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Ashlee Simpson seen on Sep 04 2008 in Beverly Hills, CA. A very pregnant Ashlee Simpson was spotted sneaking out of the back door after having lunch at Beverly Hills eatery La Scala on September 4, looking healthy and still sporting those fiery red locks. Has she still been dying her hair since she found out she was preggers? Because I don't see any roots here! Ash kept it simple with her outfit, pairing an embroidered white top (like Cake Couture's similar French Cottage Tunic in White) with vintage wash bootcut denim (like Serfontaine's Avatar Bootcut Jean in Vintage Fuzz) and flip flops. Simpson accessorized with an oversized statement necklace (check out Vevina Juji's Jelly Bean Necklace for a similar look), gradient shades and a big black bag (I'm loving Rough Roses' Whitney Tote in Black). Weight wise, Ashlee is looking very good, as she is mostly gaining in her stomach area (obviously), but looks very in shape everywhere else. Cute! It has recently been revealed that amid much speculation, Ashlee and hubby Pete Wentz are expecting a boy. Pete confirmed to Playboy Magazine recently, saying, "We know with 90 per cent accuracy that it's a boy, and our due date is around Thanksgiving." He continued that they haven't even started to think about names yet, but that he wants the boy to have a rocker-esque name. Of course he does! I wonder what doozey they're going to name this kid... leave it to celebs to go buck wild with the weird child names!

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Ashlee Simpson seen on Jul 07 2008 in Calabasas, CA. Ashlee Simpson was spotted out with husband Pete Wentz grabbing dinner at the Sagebrush Cantina restaurant in Calabasas on July 7, and I must say... these Simpson girls sure have been fond of their cowboy boots lately! Sporting a black mini dress (check out Laura Dahl's Penny Tank Dress in Black, which has a similar racerback detail like Ashlee's, or Autumn Cashmere's Halter Chemise Dress in Mochachino, for a snugglier, warmer choice) with brown boots, Ash accessorized with a vintage Chanel bag and a wristful of bracelets (Brian Nagourney Jewelry's Forget Me Knot Bracelet in Black is similar). In related Ashlee news, it seems that the "Little Miss Obsessive" singer is determined to have a healthy pregnancy, complete with regular workout sessions. Simpson hired sister Jessica's former trainer, Mike Alexander, to whip her into shape, and that is exactly what he is doing. Alexander says, "She's still clinging to the hope that she can limit her total weight gain to no more than 30 to 35lbs. So she is doing low-impact exercises, such as riding the stationary bike and Pilates." A source says that Ashlee is also being so cautious about not touching a drop of alcohol that she recently sent back a pasta dish at an Italian restaurant because she found out that it contained vodka. What do you think, dear readers... is there such a thing as being too health conscious during a pregnancy? I doubt it!

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Ashlee Simpson seen on Jul 04 2008 in Malibu, CA. Ashlee Simpson was spotted with husband Pete Wentz and puppy Rigby on the Fourth of July leaving a friend's house in Malibu, looking extremely pregnant and extremely glowing. Sporting a long, empire waist patterned frock (like Kelly Cushing's Butterfly Print Silk Dress in Blue) with black gladiator sandals and large shades (similar to Nour's Noushi Sunglasses in Crystal Mystery), Simpson finished her patriotic look off with a skinny black headband and gold locket necklaces (check out Kuo Ting Jewelry's Double Heart Locket Necklace with Seed Pearl in Gold). Very cute! While she is growing by the day, sources say that Ashlee is expecting a baby boy. A source told OK Magazine that when Pete and Ashlee stopped by posh LA baby boutique Petit Tresor, the couple "made it very clear that it was a boy. Almost everything (they picked out) is blue. They picked up a bib with "hunk" written on it." Since celebrities are known for naming their babies kooky names (considering Nicole Kidman just named her daughter Sunday), I wonder what the Simpson-Wentz's will name their tiny tot. Tuesday?

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Ashlee Simpson seen on Jun 10 2008 in Hollywood, CA. We haven't seen much of Ashlee Simpson here on CoutureCandy lately, but guaranteed that now, since she's preggers, we will be seeing a lot more of her! A.Simp was spotted leaving a meeting at the Ren Mar Studios in Hollywood on June 10, proudly flaunting the new curves that come with being with child. Work it out, Ash! For a loose cotton frock like Ashlee's, check out Ecoganik's Supima Jersey Surplus Dress in Orchid or Plenty by Tracy Reese's Long Halter Dress in Carmin. Accessory wise, Ashlee slipped on a pair of round shades (like Nour's Kiara Sunglasses in Manner Mania), held onto a studded black leather bag, and took the comfortable route by spending the day in a pair of flip flops (she's not going the Nicole Richie/Christina Aguilera route and wearing stilettos until the baby's born!). While her latest album was, ahem, less than a hit... it seems that the younger Simpson has decided to cancel her summer tour and instead spend the time relaxing and taking care of herself to ensure a healthy birth. Her spokesperson said, "After careful consideration, Ashlee has decided to postpone her summer tour. She is committed to giving her fans the best show possible, and will be back better than ever and ready to rock in the future." Jeez, talk about a cheesy statement! Ready to rock? Haha. While I don't know if Ashlee has ever rocked, or will ever again, I will say that she is looking great flaunting her new figure!

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Ashlee Simpson seen on Apr 07 2008 in West Hollywood, CA. I just recently came across this sighting of Ashlee Simpson lunching with her bandmates at Cafe Med from early March, and I decided to post it now because of how into Ash's outfit I am. Down to every detail, I think she got it just right with this look. Starting with her Chanel pearls and to-die-for blue YSL heels, Ashlee then paired a striped tank (check out Signorelli's black and white Tank with Gold Logo in Pearl Stripe) with cropped black skinnies (like James Jeans' Alex Skinny Zip Crop Jean in Black) and a pair of black Wayfies. Sportin' a black cardigan with the sleeves rolled up just enough to reveal her new tat, Ash also accessorized with an oversized black patent leather bag (similar to Aaneta's Olivia Bag in Patent Black) and a gold necklace (I think Jessica Elliot's Birds, Heart, Lock Tattoo Pendant in Vermeil would get Ashlee's stamp of approval, being tattoo-inspired and all). With all of the superstar blockbuster albums set to be released in the upcoming weeks/months (Madonna's, Mariah Carey's, etc.), it seems pretty gutsy that Simpson would release her new album on the same day as Mariah Carey. Talk about major competition! Industry insiders say, "Ashlee needs to hit a home run with this album. She really had great success with her early work, but ever since the lip synching on 'Saturday Night Live,' she's had something to prove. Her career literally depends on this album being successful." Geez, talk about no pressure or anything!

Ashlee Simpson seen on Mar 25 2008 in Hawaii. Let the celebrity bikini pictures begin! Ashlee Simpson was spotted frolicking on the beach with BF Pete Wentz, flaunting her figure in a teenie weenie yellow bikini (Tyler Rose Swimwear's Cannes Bikini is an adorable teenie weenie yellow polka dot bikini). Ashlee also showed off her new tat- what do you think? Not one to sit back while pretty much every other starlet is hopping on the "I have my own clothing line" bandwagon, Ash is set to design a line for Wet Seal, set to debut on April 22. The launch will coincide with her new album, "Bittersweet World," and will include a major in-store and online promotion. A Wet Seal spokesperson said in a statement, "Ashlee is a role model for our girl and her fun and flirty sense of style is an inspiration for the line. The goal was to partner with an icon and deliver affordable fashion, and Ashlee is an ideal partner for this. We're excited to see the designs brought to life in our stores and we look forward to Ashlee's exclusive merchandise being available across America." Can I have some wine with that cheese! Sheesh. What do you think, will you be forking over your hard earned bucks for Ash's collection at Wet Seal?

Ashlee Simpson seen on Mar 16 2008 in Los Angeles, CA. Ashlee Simpson was spotted kicking around town with a buddy on March 16, still rockin' her fiery locks (further accentuated with her bright red Wayfarers). In a basic, all black look, Ashlee started with a simple black top (like Hope & Glorie's Short Sleeve Sweater Top in Black) and paired with cropped skinny black jeans (similar to James Jeans' Alex Skinny Zip Crop Jean in Black). From there, Ash accessorized with the aforementioned shades, a patent leather bag (check out Aaneta's larger Olivia Bag in Black Patent) and a strand of Chanel pearls that I don't think really work for Ashlee's look- agree? For all the Ashlee fans out there, it seems that her new album, "Bittersweet World", is set for release on April 22. The album, which features collaborations with Timbaland and the Neptunes' Chad Hugo, is heavy on 80's influences, Simpson is the first to point out. She says, "I almost wish I lived my 20s in the 80's. A lot of the record is a bit cheeky. Sometimes I'm writing about something serious, but it was fun for me to kind of goof around as well." So, will you be picking up a copy, or will you let this one sit on the shelves?

Ashlee Simpson seen on Feb 25 2008 in New York, NY. Ashlee Simpson was spotted at TRL in New York City on February 25, promoting her new single, "Outta My Head (Ay Ya Ya)". It seems that Ashlee has tired of her prior blonde look and has opted to jump over to the red side, and it seems from her spirited attitude in these pictures that Ashlee is definitely having more fun as a redhead. Do you like her new look? Outfit wise, Ash chose a purple and blue top (similar to Parameter's gorgeous Silk Top with Applique in Eggplant) and paired it with skinny black jeans (like Deener's High Waist Cigarette Jean in Tar) and black boots. In recent Simpson news, Ashlee has confirmed that she is "promised" to Pete Wentz, but not engaged to him. Ash said that the diamond ring she wears on her ring finger "just means that he hasn't asked my dad yet." He better get word from Papa Joe before popping that question, no doubt about that! I wonder if these two pseudo-rockers get hitched if they will last, a la Gwen Stefani and Gavin Rossdale, or if Ashlee will be headed down a fellow Simpson's path, that of Jess and Nick. Thoughts?

Ashlee Simpson seen on Dec 17 2007 in New York, NY. Ashlee Simpson was spotted in New York on December 17 with boyfriend Pete Wentz, grabbing dinner prior to a night out at Pete's club, Angels & Kings. Rocking her trademark favorite shade (obviously black), Ash picked a stylish ensemble which I think is totally working for her. Wearing a black coat (check out Ecoganik's warm and stylish Fleece Wide Collar Coat in Black) with skinny black jeans (like Denim of Virtue's super skinny Patience 5 Pocket Tapered Jean in Black), Ashlee accessorized with a black clutch, black nails and edgy black ankle boots (similar to Matiko Footwear's Portia Boot in Black Leather). While the internet has been ablaze recently with rumors that Ashlee and Pete are now engaged, it seems that there was no truth to the rumor as the two have spoken out about what's really going on. Even though Ash has been wearing a mysterious ring on her wedding finger, her rep tells People Magazine "she is not engaged." Then why is A.Simp wearing a ring on her wedding finger?? They're probably just messing with the paparazzi; it's not like that hasn't happened before!

Ashlee Simpson seen on Nov 06 2007 in Beverly Hills, CA. Ashlee Simpson made an appearance at the Juicy Couture store opening in Beverly Hills on November 6, thankfully minus the scraggly long extensions and looking pretty cozy in all those layers that she's wearing! Also, can I just say that these type of pashmina/scarves are everywhere right now! Leave it to Lohan to start another fashion craze. Sporting one of these scarves with a black leather jacket, striped top (check out IISLI's super similar Rugby Tee in Black or Autumn Cashmere's Striped Crew Neck Top in Tarmac/Black) and black leggings (similar to Hudson Jeans' Skinny Leg Knit in Black), Ashley was looking probably the most natural we've seen her in quite a while... and this is quite an accomplishment! As a recent cover of In Touch Weekly proclaims, Ash has been shot up with Botox at the tender age of 23. However, Ashlee countered to US Weekly, with her rep saying "Ashlee has never had Botox in her life. She credits her eyebrows to her makeup artist who is a whiz with the tweezer." Botox or tweezers... who to believe?! Ash then dished up some of her makeup secrets to US Weekly, saying, "I cheap out and use face wipes to take my makeup off and put lotion on. I know it's very cheesy to say, but [Proactiv] is incredible. If I have a zit I put that mask on and it's gone." Let's see- Ashlee plugging the company that her sister Jessica is a sponsor for? Coincidence? I think not. How about you?

Ashlee Simpson seen on May 16 2007 in Los Angeles, Ca. Ashlee Simpson attended the Asia Society of Southern California's Annual Gala Honoring Viacom's Sumner Redstone on May 16, and actually (and surprisingly) looked prettier and more natural-looking than in recent memory! A soft hairstyle and natural makeup made Ashlee's pretty features shine through, unlike her usual tons-of-makeup look complete with Mary Kate-ish scraggly locks. Whatever she did here, though, it's working! Wearing a basic yet stylish LBD (IISLI's Ibiza Dress is similar) with gold bracelets and decorative shoes, Ash is definitely looking more mature, and it seems like that's the look she's been going for lately. With a new album in the works, Ashlee has said that she wants to have a more "soulful" sound, as she has been working with Timbaland, John Legend, and the Neptunes on new tracks. Ash told Cosmo recently that "This record is not like, 'I didn't steal your boyfriend' or anything like that. But who knows what's going to happen in the next few months. I'll probably have my heart broken and then end up with one of those kinds of songs on there." Maybe, maybe not… but either way, Ashlee says how she's "coming into my womanhood, and it's changing my music." Whether this is a change for the better, we'll have to wait and see!

Ashlee Simpson seen on May 05 2007 in Los Angeles, Ca. Ashlee Simpson was spotted leaving the boutique Tracey Ross on May 5, and her style was kind of starting to look like her pre-plastic surgery days, as crazy as that is to believe! Wearing a striped tee (Signorelli and IISLI make similar tees, take your pick) with knee length black shorts, Vans sneakers and black Wayfarers, Ashlee incorporated a little bit of that edgy-ish style she used to be known for. Someone who might not like Ashlee’s style right now, or even Ashlee period, is older sister Jessica. Star Magazine is reporting (remember the source here, people) that Jessica and Ashlee are having a downright girl-fight! A “source” at Star says that “there’s certainly a sibling rivalry between them.” Jessica might hold resentment for Ashlee due to one incident in particular with her ex-BF John Mayer, when John asked how old a picture of Jessica was, and it actually turned out to be Ash! Talk about apparently touching a nerve! While this is 99.99% most likely totally gossip, it’s still fun to talk about, don’t you think?

Ashlee Simpson seen on Apr 26 2007 in Hollywood, Ca. As Ashlee Simpson walked down the beige carpet (?) last night, April 26, at Us Weekly's Hot Hollywood Party, I had to think, was she inspired by Dorothy from the Wizard of Oz? Wearing a Brian Reyes striped dress (Walter's striped dress is similar) with bright red shoes and a clutch, Ash was definitely channeling Dorothy. Striking poses is obviously nothing new to Ashlee, who is featured in May's issue of Harper's Bazaar, clad in designer duds and finally talking about her drastically changed look. When asked about her rumored (and obvious) plastic surgery, Ash simply says how "I loved how I looked. I’m not an insecure person, nor was I before. It’s a personal choice. I believe if somebody chooses to do plastic surgery, it [should be] for yourself, not for anyone else.” Well there's a textbook response if ever I've heard one. At least her philosophy on life seemed a little more genuine, as Ashlee told the mag how she "just wants to have fun. Life is too short…through all my changes, I’m still the same person." Ash still seems to be comfortable with herself, which in the end is truly the most important thing.

Ashlee Simpson seen on Apr 17 2007 in Hollywood, Ca. Ashlee Simpson and bisexual boytoy Pete Wentz did their usual routine and hit up Parc on April 17, but the one question that just has to be asked is…. Why is Ashlee's hair two different colors? It's like the top of her hair is a dark blonde/light brown, and the bottom of her "hair" (read: extensions) is platinum blonde. Come on, Ken Paves, step up your game! Besides the whole hairstyle faux pas, Ashlee stuck to a basic black ensemble (with the exception of a pair of firetruck red pumps) of black denim capris (like the 10 Inch version of our 14 Inch J Brands), a black cami with a black jacket over it, a patent leather Prada bag and a gold necklace. TMZ is reporting that one of the perks of dating Ashlee is havin' yo bills paid for! It seems that Pete has found himself a little sugar mama, because after the twosome left Parc (and Ash paid for the valet) and headed to fill up the tank of Pete's Range Rover, Ash once again scrounged around in that behemoth bag of hers for money to give to a homeless man who serenaded the two at the gas station. Now there's a song I would pay to hear! Let's hope Pete plays his cards right if he wants to keep riding on this gravy train.

Ashlee Simpson seen on Apr 12 2007 in New York, NY. Ashlee Simpson hit up the opening of a new club, Runway, in New York on April 12, noticeably lacking something (or should I say someone) who she's been very attached to lately, new boyfriend Pete Wentz. Wearing a black babydoll tunic dress ( Zoa makes a similar one in black) with black tights, a silver ring and holding a black clutch, it was nice to see Ash crack a smile, considering how whenever she usually goes out at night she's pouting to the max. Just one minor style-related comment: would it have killed ya to get a manicure, pre-event, Ashlee? Yikes. Pete must not mind her terrifyingly chipped nails, however, as the two recently took a secret trip to Cabo, and have been spotted leaving Hollywood hotspot Parc, hand in hand. Inside Parc, however, the twosome was even more intimate. Sources say Pete and Ash "cuddled up in a semi-hidden booth, holding hands, gazing into each other’s eyes and smooching in between Simpson’s dance sessions with a group of girlfriends. They definitely weren’t hiding the fact that they were together. They were making out a lot and they were pretty intense.” Considering Pete recently admitted that he enjoys making out with other boys, we'll see if this is a match made in heaven, or one that will be over before it really began.

Ashlee Simpson seen on Apr 02 2007 in Los Angeles, Ca. Ashlee Simpson has been looking quite forlorn lately. Whether she's leaving new hotspot Parc or seen here shopping in LA on April 2, seeing Ash crack a smile is getting rarer and rarer! What does the young Simpson have to be so sad about? The fact that the general public thinks she is only marginally (if that) talented, or how she must not even recognize herself when she looks in the mirror? Jealousy over the fact that her big sis Jessica is in a steady new relationship? I don't know about the first two, but I know that Ashlee has nothing but well wishes for her big sister. Seems like Ashlee has given John Mayer her "Simpson Stamp of Approval" after 8 months of dating Jess, as a friend of the family told People magazine that "Ashlee loves John. She thinks he is great for her. More importantly, Jess is happy." While it's great that Ashlee approves of Mr. Mayer, I feel like he has made Jessica totally Blah with a capital B! While there are still those rumors that Ashlee is dating Pete Wentz, only time can tell when she is actually going to find a man to call her own. You can snag Ash's casual look here by picking up a pair of vintage wash bootcut jeans with a long black tank, grey hoodie, black beanie and her fave black Wayfarers.

Ashlee Simpson seen on Mar 09 2007 in Los Angeles, Ca. Ashlee Simpson headed to (who else) Ken Paves on March 9 to get her hair done, and the two most likely gossiped the whole time about who’s dating who, giggling like little schoolgirls. As Ashlee left the salon in dark skinnies and a button-up coat, I have to say, her extensions look very obvious! Just saying!

Rumors have been swirling lately that Ash is making a move on none other than newly single Ryan Phillippe, and that the two were getting quite cozy at Les Deux on March 3. Sources say that the two arrived separately, and when Ryan arrived, he found his way to a seat at Ashlee's table. An onlooker says that Ashlee looked really excited, and that it was obvious that she had a crush on him. The troublesome two then headed to The Library, the clubs VIP section, and emerged a few hours later looking "tousled". I love that word. Reports say that they then headed to Ryan's bachelor pad, where Ashlee spent the night. Just gossip, or is this a new celeb hookup I smell?

Ashlee Simpson seen on Feb 28 2007 in Beverly Hills, Ca. Seen shopping in Beverly Hills on February 28, Ashlee Simpson stayed quiet and shied away from the photographers' questions, for a sunny day of solitary shopping. Wearing medium wash jeans tucked into black boots with a navy tee and black sweater, Ashlee was quite bundled up for being in LA! But what might have been most noticeable about her outfit are her bright red sunglasses… looks like Sally Jesse Raphael's trademark look might have been Ash's shadespiration!

Ashlee has also been in the middle of romance rumors this week, with Fall Out Boy bassist Pete Wentz publicly denying the fact the he and Ash are an item. While it's true, the troublesome two have been seen kissing and holding hands recently, Pete says that it is definitely nothing serious. He tells Rolling Stone that "maybe in a different universe, we'd be some hot couple, but not in this one. I'm attracted to creative people and train wrecks, and there's no shortage of that in Los Angeles." So what are you saying Pete, that Ashlee's not creative? Hey, he said it, I didn't.

Ashlee Simpson seen on Feb 03 2007 in Studio City, Ca. From one Ashley to another, it seems that Ashlee Simpson enjoys going out in public with older sis Jess, due to the fact that besides spending time with her beloved sibling, she gets to be ignored by the paparazzi who clamor for a shot of the older Simpson. When Jessica met up with a friend on February 3 at the Mexicali Cocina Cantina Restaurant in Studio City, Ashlee joined the two a little later for the remainder of their meal. Wearing medium faded jeans with a black short sleeve tee (get yours a few sizes too big to wear it baggy like Ash does), black boots, a silver ring and Ron Herman Free City hoody, Ash did get her fare share of the flashbulbs.

But, Ashlee has been quoted as saying that Jessica usually gets more of the attention and autograph seekers when they are seen together. When one fan who Ashlee posed for a picture with asked her "why the photographers ignore her all the time," Ash said that she is "thankful for that!" In this crazy world of It Girls not even being able to go to McDonald's without being swarmed by the paps, I'm sure Ash can take any breather from the photogs she can get!

Ashlee Simpson seen on Dec 10 2006 in Los Angeles, Ca. Ashlee Simpson leaves LA store Hollywood Rag on December 10 looking quite warm and cozy, but take into consideration where she is. In True Religions, a white thermal, a blue scarf, a black beanie and a black sweatshirt with fur hood, Ash braved that near subarctic Los Angeles weather. What was it, like 65? Anyways, In Touch is reporting this week that Ashlee has given away some of her barely-worn designer duds to her loyal cleaning woman, Maria. Instead of just letting these pricey outfits collect dust in the nether-regions of her closet, she has gotten into the holiday spirit and given these outfits as a gift to Maria, who in turn has sent some of the pieces back to her family in Brazil. Let's hope that these Brazilian family members are a size 0!

Ashlee Simpson seen on Dec 03 2006 in Los Angeles, Ca. Just when it seems that Ashlee Simpson's addiction to plastic surgery has calmed down a little, there are new reports claiming that Ash wants desperately to get her rear filled out with butt implants! The source claims that Ashlee "wants to look better in jeans" and, now that she's lost a considerable amount of weight, thinks that her "flat butt looks even flatter". Butt implants? Really, Ashlee? I think we should take this goss with a grain of salt, but looking at how Ash spent over $130,000 on plastic surgery this year alone according to NW Magazine, who's to say what procedure she won't go under the knife for next! It is a little scary to think that, at the young age of 22, she has had more work done that some women twice her age!

Ashlee stepped out in Los Angeles on December 3, wearing a black tee with Tom Ford's stunning Whitney sunglasses. After the Coffee Bean, do you think she was on her way to her surgeon's for a festive holiday gathering?

Ashlee Simpson seen on Nov 18 2006 in Hollywood, Ca.

First off, let's start with a little game of guess who, shall we? Is this billionaire twin fashionista Mary Kate Olsen? Nope. Tanorexic stylist to the stars Rachel Zoe? Try again. It's Ashlee Simpson silly, and man she really wants to be an Olsen, doesn't she! Spotted shopping on (where else?) Robertson Blvd. in Hollywood on November 18, it appears that Simpson might be taking baby steps to return to her previous rocker image. In a black scarf and True Religion jeans, Ashlee was also rockin' Tom Ford's new pair of Whitney sunglasses with a beat up old pair of Chuck Taylors. And we all know that Converse are the official sneaker of the punk rocker, so does this mean Ashlee will return to her (faux) punk roots?

Maybe, maybe not, but a musical comeback is definitely in Ash's near future. At the final performance of her role as Roxy Hart in Chicago, music legend Robert Smith of the Cure was in attendance, and Ashlee could barely contain herself. She says that "to work with Robert Smith would be an honor!," flirting with the idea that the two would be collaborating on a future record. Just make sure that Robert has actually agreed to work with you Ash, before you tell everyone that he is!

Ashlee Simpson seen on Nov 14 2006 in New York, NY. Ashlee Simpson is now back in the US after her London engagement in which she starred in the musical "Chicago," and she has definitely wasted no time in the romance department! Just getting out of the relationship with her bandmate, Braxton Olita, Simpson was spotted at celeb breeding ground Hyde in Hollywood with Fall Out Boy singer Pete Wentz, who she allegedly had a brief fling with earlier this summer. Wow, Ash sure doesn't waste any time! Will Ashlee and Pete be this falls newest couple? Only time will tell. In the meantime, Ashlee showed up on November 14 in NYC for the 10th Anniversary of Chicago, sporting a curly, childlike bob. Where is Ken Paves when Ashlee needs him! Bring some of sister Jessica's HairDo extensions, stat! At least her cute black lace tunic was a smart move, I just wonder what kind of music she's going to make now, because you know that fake-punk rock sound just isn't going to cut it with this new glam image she's got goin' on!

Ashlee Simpson seen on Oct 10 2006 in London, England. Ashlee Simpson strikes her best seductress pose at a recent charity event in London, where she has been holed up lately while she stars in the musical "Chicago". I have to give Ash credit here, though. Even though she's still sportin' those ratty extensions, she really pulled together a classic look here. In a mini cocktail dress with clean lines, Ashlee proves how much she has matured lately. And while the world is still abuzz about how much work she really has had done to that mug of hers, I've got to hand it to her, she is looking pretty hot these days.

To get Ash's sleek look, go for a killer classic cocktail dress, like our Eskell Bonfire Open Back Dress, which is like a sleeveless version of Ashlee's. I mean, just check out that sexy back!

Ashlee Simpson seen on Oct 06 2006 in London, England. While Ashlee Simpson has opened to mixed reviews in her role as Roxie Hart in the musical "Chicago" in London, that's not stopping her from getting her weave on! Stepping out to dinner at Nobu, Ash took a much needed night off from rehearsals. While I have to applaud Ash for stepping outside of the norm and branching out to do a musical, I just don't see it! Ashlee seems too young to be in the role of Roxie, especially compared to the actress playing Velma, who looks to be about 40! It almost seems like Ashlee could be her daughter when looking at stills from the production. On the other hand, this all might have been a part of Ash's plan to one-up her sister, as Jessica is presumably stewing over the fact that her younger sis beat her to musicals. Boo hoo Jess, you're always crying about something!

For Ashlee's more mature and conservative look, start with a black blazer, similar to our Da-Nang Woolen Woven Blazer in Black, and wear with a floral buttoned top, like our Charlotte Ronson Button Down Blouse with Tie in Plum. For the jeans, opt for the super skinny Paper Denim & Cloth Super Slim Zipper Cigarette Pants in Olivia, and you'll be ready to make your musical debut too.

Ashlee Simpson seen on Aug 22 2006 in Manhattan Beach, California. When Britney and Christina modeled for Skechers at the height of it's late-90's popularity, the pop princesses faces helped sell many-a-sneaker. Now, Ashlee Simpson is taking the spokesperson title from them, and is the new face of Skechers. Wait, did I hear what I just said? Who knew Skechers was even still around? From the looks of this picture from the photoshoot on August 22 in Manhattan Beach, Skechers is trying to revamp their demographic from tween girls to, I don't know, rockers that hang out in graffiti strewn alleyways? I don't know, but seems like a long shot to me. To get Ashlee's outfit, however, grab the Morphine Generation tee she wears, the Skull T-Shirt with Gunmetal Foil, and pair with a pair of zippered pants, like our Bambu Tyger Indochine Pants. One thing is certain, the Simpson girls sure know how to attach themselves to products!

Ashlee Simpson seen on Aug 20 2006 in Los Angeles, Ca. Apparently a human cloning machine was invented and I am the last to know about it! As Ashlee Simpson makes her way to Hyde Nightclub in Hollywood, she is seriously a straight up doppelganger for Mary Kate Olsen. All that’s missing is the yard of fabric as clothing! In light of her recent transformation, Ashlee does look hot here, and the reason is all in the jeans. In Ashlee's favorite wash, her gray jeans, similar to our Joe's Jeans Chelsea in Getz superbly flatter her petit frame and show off those hot patent leather shoes of hers. This vibrant color works well for her too, and with a basic black cami underneath, like our Signorelli Basic Two Sided Tank in Black, and bangles, like our Rebecca Norman Wavy Thin Bangles in Vermeil piled on, Ash seems ready to dance her booty off in the club. It'll be interesting to see what starlet she turns into next!

Ashlee Simpson seen on Aug 09 2006 in Los Angeles, Ca. Constantly changing her look, and now with slightly darker tresses, Ashlee Simpson goes for a summertime stroll in this adorable white sundress. Every girl needs to have a breezy sundress in her closet for the summer months, and our Karanina Pansy Dress in White is the perfect dress for any summertime event. While everyone is saying that Ashlee is going through an identity crisis (Who will she look like this week? Jessica? Mischa? Mary Kate?), it seems to me that this Simpson is still playing with looks that work best for her. Work it out, Ash!

Ashlee Simpson seen on Jul 22 2006 in Los Angeles, Ca. It seems that Ashlee Simpson has a new little friend as she steps out of her tourbus a few days ago. Toting around her adorable new Yorkshire terrier, Ashlee is the epitome of California cool. With an oversized vintage tee and fedora hat, Ashlee throws on a rockin' pair of True Religions, the Bobby Earth Rainbow Big T's in Saddleback with a pair of gray slip on Vans. She's got her Vans on and they look like sneakers! And as if wearing a hat doesn’t make you incognito enough by itself, wear a pair of huge aviators, like our Oliver Peoples Commander Sunglasses in Black. Now completely unrecognizable from her black hair, big schnoz days, Ashlee looks hot!

Ashlee Simpson seen on Jul 19 2006 in New York City, NY. At the launch party for Victoria's Secret Pink Line, which Ashlee Simpson was recently named the spokesperson of, it's easy to assume that the focus was less on Pink and more on Ashlee's barely there dress and her new Ken Paves line of hair extensions! But back to her outfit, this dress was one that definitely caused people to take notice! Super stylish designer Ya-Ya can take credit for this floral party dress, and although we feature more of their casual pieces on our site, like long tanks and sheer wraps, they can rock out a cocktail dress too. It's just hard to believe that this is the same Ashlee Simpson who once sported jet black hair and a punk wardrobe from head to toe!

Ashlee Simpson seen on Jul 08 2006 in Los Angeles, Ca. Did Ashlee raid big sis Jessica's closet, or does she just love her Nation Ltd Short Sleeve V-Neck Tee in White as much as her sister does? Either way, it has already been established that this tee is an essential that every girl should have in her closet, to be worn day or night. Just like Jessica loves her Oliver Peoples Athena Sunglasses, Ashlee is obsessed with her Oliver Peoples . What can I say, the Simpson's love their Oliver's! What I still don’t understand, though, is what is Ashlee possibly carrying in 3 bags!

Ashlee Simpson seen on Jun 11 2006 in Los Angeles, Ca. While it's unclear whether or not this picture was take pre or post Ashlee's nose job, which she still hasn't fessed up to yet, Ash is sure sportin' some serious weaveage! And no, that's not a misspelling of cleavage, I'm referring to her oh-so-obvious weave that she has going on.. I mean there are two distinct hues of blonde in her hair! Either way, Ash's new look is about a bajillion times better than her scary pale phase, and as she continues to evolve her look, her style evolves right along with her. In the super hot J Brand 12 Inch Pencil Leg Jeans in Gray, and a sheer black tank like our American Vintage Double Strap Cotton Tank in Noir, Ash is at the forefront of fashion. Only time can tell if she will eclipse big sis Jessica in terms of personal style!

Ashlee Simpson seen on Jun 01 2006 in Los Angeles, CA. At a recent performance, Ashlee Simpson flaunts her newly blonde tresses and significantly slimmer sniffer, in a basic top combination that is super easy to achieve. To get Ashlee's layered look, start with the same basic white tee that Ashlee wears, the Nation Ltd Short Sleeve V-Neck Tee, and pair it with a classic black tank like our Saint Grace Low Back Textured Rib Tank in Black. Cue a smoky eye and some black nail polish, and you've got this Simpson's stage look down pat. Unfortunately for Ash, though, her summer concert ticket sales have been less than spectacular. At a recent performance, she performed for a crowd of 700 in a stadium that seated 6,500. Ouch!

Ashlee Simpson seen on May 28 2006 in Los Angeles, CA. Wait, which Simpson is this? Now that Ashlee has gone blonde, gotten her honker shaved down, and plumped up her lips with some collagen, the only phase of her transformation into Jessica she has yet to complete is the boob job! While Jess has yet to blab about what she thinks of little sis’ transformation, it’s a safe bet to say that no one wants to have a case of the Single-White-Females, especially from your little sister! While running errands in Los Angeles (with a bag, doggy carrier AND coffee, no less), Ashlee is at the height of fashion right now, wearing her J Brand 12 Inch Pencil Leg Jeans in Black with a Nation Ltd Short Sleeve V-Neck Tee and a basic hoody similar to our Mike & Chris Long Sleeve Sam Zip-Up Hoody in Black. Oliver Peoples Commander Aviator Sunglasses in Gold complete the look. Have to admit, this Simpson is lookin' good!

Ashlee Simpson seen on May 23 2006 in Los Angeles, CA. In a sighting that appears to be before the infamous nose job, but not before the blonde dye-job, Ashlee Simpson is seen at LAX boarding a flight to some fabulous local, undoubtedly. Following big sis Jess' example yet again, Ashlee goes casual in the Bobby Big T in Easy Rider style of True Religion. And everybody knows that you need to have an uber comfortable hoody when traveling, so one such as the Mike & Chris Long Sleeve Sam Zip-Up Hoody lets you travel in comfort and style. Throw on a checkered fedora and grab an Ugg doggy carrier, and you're in business.

Ashlee Simpson seen on Apr 24 2006 in Los Angeles, CA. The stylish Ashlee Simpson has gone gray! In Touch magazine pictured Ashlee Simpson wearing a pair of gray jeans.

Ashlee Simpson seen on Oct 30 2005 in Los Angeles. Rebel Yell is one of the most clamoured-for brands by celebrities and fashionistas alike, and Ashlee goes casual in her tan Rebel Yell shirt.

Ashlee Simpson seen on Jul 23 2005 in Los Angeles, CA. Ashlee has taken a liking to Grail's destroyed skull tees, transforming her from a pop princess into an edgy rocker. Funky yet still cool... Grail is a must have for celebs and fashionistas alike.

Ashlee Simpson seen on Apr 27 2005 in Los Angeles, CA. Ash wears the Bobby cut of True Religion denim, as she strolls through the street for a casual day in Los Angeles. Paired with a cotton top and scarf, this outfit is perfect for catching lunch with friends or stopping in to the hottest boutiques.

Ashlee Simpson seen on Mar 20 2005 in Beverly Hills, CA. One of Hollywood's greatest chameleon's, Ashlee Simpson can go from frilly and girly to a fabulously punk rock without blinking an eye. Spotted roaming Beverly Hills, the singer rocked a fantastic and totally unique (true to Simpson style) look. Pairing a casual tee and Jessica Eliot antique key necklace, and her Oliver Peoples (a fav with her big sis also) Simpson proved that in fact all Simpson's shop in style. Although maybe it would have been a better idea to just bring someone to accompany her on her shopping excursion, instead of just chatting it up on her cell the whole time!