Black Sheep Syndication

We love how edgy she's gotten over the years!

Ashlee Simpson is currently in the Big Apple for NY Fashion Week, and the singer is pulling out all the stops when it comes to her runway show looks! The blonde beauty emphasized her tiny frame in tight leather pants, a blouse, and a black fur jacket when she stepped out yesterday, and it appears that someone might have hired a stylist!

Poor Ash had to deal with a bit of embarrassment later in the day!

As she walked the red carpet for the Garnier Fructis Blow Out Bar and Style Station Party, guests and reporters didn't recognize who she was and mistook her for High School Musical star Ashley Tisdale.

How mortifying!

She definitely has different style than her older sister!

Ashlee Simpson made her way through JFK airport yesterday, and the former pop princess looked more like a punk princess in skinny jeans, sneakers, a beanie and a leather jacket. The only element of her outfit that was the slightest bit girly was her favorite Chanel necklace.

The blonde beauty had a relaxing couple days in the Big Apple! On Sunday, the single mom enjoyed a day of shopping with her girlfriends in the West Village before stopping to get a caffeine fix.

We bet Auntie Ash knows if Jessica is expecting a girl or a boy, and we're dying for her to spill the beans!

All good things have to come to an end unfortunately!

Ashlee Simpson and her son Bronx touched down at LAX yesterday after spending the holidays in Hawaii with mom Tina and sister Jessica, and the blonde singer was all smiles as she toted her baby boy through the airport. A little down time clearly put her in a cheery mood for the New Year!

Ash must be thrilled to become an auntie again! While on vacation in tropical paradise, Jessica confirmed that she was expecting her second child with fiance Eric Johnson by writing "big sister" in front of her daughter Maxwell in the sand, then tweeting a bare belly shot of her growing baby bump.

Noticeably absent from the Hawaiian gathering? Papa Joe Simpson, who has been laying low since his rumored gay confession and subsequent divorce filing in October.

Ashlee Simpson decided to give her son Bronx a lift when the adorable pair arrived back in Los Angeles on Friday after they touched down at LAX.

The 28-year-old entertainer seems more focused on family since her recent split with Vincent Piazza earlier this week. The duo began dating last year after she split from ex-husband Pete Wentz but broke it off over the Thanksgiving holiday weekend due to scheduling difficulties.

Looks like Bronx will be spending more time with mommy!

Another one bites the dust!

Ashlee Simpson and Vincent Piazza have split after a year and a half together.

"There was no bad blood and no third party involved. It was honestly just a long distance relationship and it became too hard to make it work. It's not necessarily forever and they could get back together. Nobody is to blame. Just the distance," a source dished to Us Weekly.

The singer and the Boardwalk Empire star began dating in June 2011 after the blonde beauty split with husband Pete Wentz.

Miss Simpson is bound to be lonely now that everyone around her is coupled up. Her sister, Jessica Simpson, is happily engaged to Eric Johnson, and her former beau is in a steady relationship with model Meagan Camper.

Something tells us Ash won't be single for long!

Ashlee Simpson is giving us a sneak peek at her new "Bat For A Heart" music video, and this is also the first song she's released in four years. We can't believe it's been 8 years since she burst onto the scene with her debut album, Autobiography!

“Happy Halloween! As promised, here’s a little tease of what’s to come!” Ashlee tweeted. “In this tease I do drop the F bomb so you’ve been warned!”

The 28-year-old singer/actress shows a lot of skin and looks like a hot mess in some of the shots, but she still looks pretty sexy. But how's the sound? You tell us! We're reaaaally curious as to what the rest of the video (and her forthcoming album!) will be like!

Ashlee Simpson was spotted meeting up with a friend for lunch today in Studio City, wearing her favorite Anine Bing jeans, and while the singer/actress has always been on the slimmer side, it looks like she's lost even more weight over the last few weeks.

We're not sure what's eating away at her, but rumor has it she's barely on speaking terms with her big sister Jessica! According to a source for OK! Magazine, Jess turned to Ashlee for support this summer when she was trying to lose her baby weight, but when Ashlee "showed very little sympathy for her, Jess lost it." The source added that Ashlee believes Jessica “only has herself to blame” for her weight troubles. Ouch!

“She was devastated and hit back, saying Ashlee is jealous of the attention she gets. It turned into a massive fight," the insider added. “Ashlee used to feel like they were friends. They would party together, but ever since Jess decided to have a baby, she’s way more straight-laced. It’s alienated Ashlee.” Hmm, think any of this is true?

Welcome back Ash!

Ashlee Simpson was looking slim in an Anine Bing black leather jacket and skinny jeans when touched down at LAX yesterday. Look who's coming back to town in style!

The 27-year-old entertainer just came back from attending the the season three premiere of Boardwalk Empire in New York City earlier this week and we bet she can't wait to get her hands on her big boy Bronx!