She doesn't always get the proper credit for it, but Ashlee Simpson is a women of great style. While her music career has stagnated a bit in recent years, the supremely fashionable singer is still too often compared to her big sister — you know, that singer/actress/worth-millions designer Jessica. Now that Ashlee Simpson is pregnant with her second child, and first with new hubby Evan Ross, I look forward to seeing how she dresses her bump since I have always admired her rock chick style.
The younger Simpson sister has always had a more rock 'n' roll-informed point of view with fashion, thanks to her clothing choices and willingness to experiment with hair of all lengths and hues. Meanwhile, Jessica has always trafficked in more of a sexy Texan look, with her big, blonde, and voluminous hair and her figure-hugging clothes serving as her signatures.
These are some of Ashlee Simpson's best looks through the years and they remind us that no, she is not Jessica's fashion twin. Her look, especially her more street and casual ensembles, is uniquely her own.
Boho Chic Layers
While she has the same flowing blonde waves as Jessica at times, Ashlee’s long and chic boho layers were a modern update of Stevie Nicks’ style. Total rocker babe, right?
Her high-waisted, black leather pencil skirt was already rock ‘n’ roll to begin with. She added a blush graphic tee for further punch.
Simpson’s leather burgundy shift didn’t have a lot of movement, but she sure looked like a rock goddess.
If there is one thing I’d wager money on, it’s that I’ll never see Jessica Simpson hack off her long, flowing, and wavy locks. Ashlee, however, has gone super short, like with this white-hot pixie.
Red Hair, Don't Care
Ashlee has been blonde, brunette, and black-haired. But when she went red, it elevated her unique style to a whole other level. She can pretty much pull off any shade or length. Really!
Ashlee's Take on the LBD
LBDs are LBDs. We all own several and wear them. But this LBD, with the peep-toe booties, was decidedly Ashlee.
Simpsonized Street Style
While Jessica has been seen in floral dresses with leather jackets black tights, her little sister’s version of this popular street style comes with a knit beanie.
A. Simpson is not a big shower of cleavage. She tends to remain covered up without looking frumpy. This ladylike and sleeveless black lace frock was her exercise in elegance.
X Marks the Spot
Another LBD… but with an edge! Simpson’s short cut and the X across her chest were simple but standout touches.
V for Vendetta
This is a personal favorite. Simpson is super deft at taking a simple LBD with interesting elements and dressing it up with things like a short, platinum ‘do.
While a vintage-look rock tee paired with leather leggings and a jacket is not a new rock chick convention by any means, it was so effortless on Simpson. It looked put together without too much thought and it was a casual, street style win.