There are perfectly good celebrity style moments, and then there are the looks that really stick with you, the ones you try desperately to recreate at home. In 'Great Outfits in Fashion History,' Fashionista editors are revisiting their all-time favorite lewks.
There was a time — at some point between her infamous "SNL" performance and the 2012 presidential election, to be more precise — that I counted Ashlee Simpson as something of a style icon. How much of that had to do with the fact that she was living my pop-punk princess dreams, floating seamlessly between the backstage area of Fall Out Boy concerts and the VIP section of NYC nightclub Angels & Kings with then-husband Pete Wentz? That's one secret I'll never tell.
But revisiting some of Simpson's looks from that time, I can see what resonated with me. For big red-carpet appearances, Simpson took inspiration from old Hollywood and '20s flapper glam and gave it a cool, MySpace-worthy spin. Take this romper she wore to the 2009 InStyle summer soirée, for example: It's by Jill Stuart (then the fashion brand for cool young starlets); the champagne satin is a classy choice, and the bustier neckline feels much hipper when combined with the tap-short shape at the bottom.
Simpson plays up that contrast with a pile of long pearl necklaces, a white clutch by Dolce & Gabbana and leg-elongating pumps from Brian Atwood. She keeps the beauty look unfussy, going for a smoky eye and (arguably too) undone hair.
It's the kind of look I'd have blogged about on my LiveJournal, but honestly, there are parts of this I'd still wear today. Shop Simpson-inspired picks in the gallery below:
Please note: Occasionally, we use affiliate links on our site. This in no way affects our editorial decision-making.