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StyleHiving: Get Ashlee Simpson’s Date Night Looks

Ashlee Simpson has had her share of hits and misses in the style department, from her days as a wild punk rocker (miss) to her transition to a buxom blonde (hit), and hundreds of other looks, hairdo’s, styles, and so on in between. However, ever since she hooked up with Fall out Boy lead singer Pete Wentz, Ashlee seems to have come into her own and developed a unique signature style that is a part punk, part sexy vixen, part avant-garde trendsetter, that suits her to perfection (come on, you know you kind of hate yourself for it, but you have to admit you’re kind of starting to envy her style!). In pictures of the two, Ashlee looks absolutely radiant- serving as further evidence to the universal truth that feeling good is the most essential ingredient to looking good. For my next ‘date night’ edition, I looked to Ashlee for inspiration. She always looks confident, happy, sleek, and never overdone.

1) The button down shirt dress keeps her look laid back and casual, while the thigh-high boots add a large dose of sex appeal for a look guaranteed to hike up any red-blooded man’s heart rate. Ashlee kept the accessories to a minimum which enhanced the laid back, effortlessly sexy vibe of the look.

[Rag & Bone Flemming Dress, $495; Shipley & Halmos Button Front Sift, $344; Pedro Garcia Suede Platform Boots, $420]

2) When a dress is not in any way revealing, yet still manages to be insanely sexy, you know you have a date-night winner! This sleek body-con dress hugs Ashlee’s curves in all the right places but still leaves more to the imagination. Ashlee kept the look young, fresh, and not to over the top by keeping it basic and unfussy- minimal accessories, a bold bag, tousled hair, and rich makeup.


[Vivienne Tam Sleeveless Seamed Shift Dress, $374; Nashelle Bracelet, $81; Goldenbleu Emerson Red Patent Clutch, $280]

3) For a safe date-night option, look no further than this image. A loose, but not too billowy blouse with ultra skinny jeans and boots is the perfect choice when you have no idea how fancy or casual your date-night destination will be. This look is fun, effortless, and has that whole- I’m-sexy-without-even-trying-to-be vibe which no man can resist.


[J BRAND Jett 12" Pencil Split Bottom Skinny Jeans, $165; Vena Cava Shaman Blouse, $324; Steve Madden Intyce Black leather Boots, $199]

[All photos of Ashlee Simpson provided by StyleHive!]

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