Ashlee Simpson’s bright yellow dress screamed Summer. She wore it simply and well, adding only an orange toned bag, embellished headband, and casual flip-flops. A great day-time look.

Ashlee Simpson took her son, Bronx, to the Children’s Museum of Manhattan, dressed comfortably and stylishly in sneakers and a 3.1 Phillip Lim tank. Her zipper-bottom jeans and Balenciaga bag help give this look an edgy feel.

Admittedly, we never really thought that wearing a hot pink tailored coat (or, I mean, not tailored too) was a good idea, but oh my god, look how cute Ashlee Simpson looks in it? Teaches us a lesson.

Va-va-voom outerwise is so so SO in this winter. Have you seen all those gold python jackets? Patent leather trenches? Why not add hot pink to the mix. Take a tip from Ashlee, though — when you’re going with a super-loud color, tone down the texture of the fabric. Hers is a demure wool. We like that. And other sleek things — like waterproof cotton canvas, a la Burberry.

Get Ashlee’s look — but take it to the extreme with a head-to-toe smattering of black and white stripes. B/W stripes have become de rigeur amongst the rock star set in recent years — stemming from the emo-indie youth movement, of which Ashlee’s boyfriend Pete Wentz, is at the crux of.

When you’re dressed down to a T-shirt, jeans, and flip-flops, there’s no reason to hold back with your accessories.

I like to call it putting on the whole house — and that’s exactly what Ashlee Simpson’s done here. On top of her casual outfit she’s stuck a trilby, enormous sunglasses, and a huge patent leather bag. Sweet.

Though it’s hard to wear pale grey any time of the year, it’s even trickier to wear it against bare skin. To pull of Ashlee’s look, get a golden spray-on tan, so your skintone doesn’t pale against the ashy steel. And pair with bold accessories – like a sharp structured black clutch and flashy red shoes. Va-va-voom!

Dressed down to kill, Ashlee Simpson shows off her toned legs in denim hotpants. For those of us who haven’t yet managed to banish the jiggle from our upper-thighs, try a longer shorts or a mid-upper-thigh cut. We love the gingham check — one of the hottest trends of the season.

Ashlee Simpson may be most infamous for bad lip synching and her recent plastic surgery makeover, but despite her nouveau take on stardom, her wardrobe’s all classic casual. Here she sports Ray Ban’s Classic Wayfarers, a Ramones rock T-shirt, and a smart black and white bag.