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He can wear it all together—or break it down for about a billion (okay, slight exaggeration, but close) different looks. Click through to shop each piece.

Denim on denim is the way to go, but this will pair just as nicely with cords or cargo pants.

A little attitude goes a long way.

I mean, you could buy jeans at four times the price (but they wouldn't be any cooler).

Not that cheap for a belt, but it will add instant punch to any oufit and last for years.

Color contrasting high-tops stand out.

Total adorableness, for under 100 bucks. Click through to shop each piece.

Sure, it goes with jeans, but be adventurous—mix it with another print.

Just the right amount of flounce, and a cute-as-pie pattern.

A school girl classic that will never go out of style.

A bit spendy, sure, but the imitations pale in comparison and these will look great with skirts, dresses, patterned tights, leggings and skinny jeans—really, you can't go wrong.

Clever and cute.

Every girl needs a little bling--but the traditional color keeps this from being cute overkill.