Grown-Up Grunge — We love how buttoned-up but roughed-up the sheer-plaid trend is, and how they can make a sophisticated look less stuffy and a dressed-down look less casual. With cutoffs, they make for a perfect combination of grunge and glitz that even Courtney Love would approve of.
Celeb Clue-In — We could create our own celebrity tabloid if we gathered every single image we've seen of this exact outfit: a slouchy tee, a butt-length blazer, cutoffs, and heels. But there's a reason it's so ubiquitous — it's because it works. Longer length cutoffs have a tendency to swallow your body, but with just a bit of tailored structure with the jacket and shoe, the shorts can feel effortlessly chic.
Extreme Canadian Tuxedo — Tucking a chambray button-up into a pair of cutoffs is a go-to trick of ours. How to bring it to the next level? By indulging in all the patchwork trends we've seen in shops.
Comme Des Garçons — We consider bateau striped tops a magical neutral. It blends into any other item, but always makes things seem more interesting. With a leather briefcase, fun oxfords, and your favorite ripped-up jeans, the look is full-on Jean-Luc Godard (but you'll feel more like Anna Karina — promise!).
Slim Jims — Let's face it. Most of the jeans fit to cut up are skinny jeans and not the relaxed fit ones cutoffs are usually made of. For a sophisticated take on the cutoff, snip the bottoms off a pair of skinnies, cuff 'em twice, and wear them with your highest heels.
Hang Out — Though this look isn't for everyone, we do love it for those among us who can't get enough of short-shorts. If you're hesitant on showing so much skin, cover up a bit with an oversized oxford and boots. Just make sure your shirt is tucked in front to ensure that no one will mistake you for having left your pants at home.
It's All White — One of the easiest ways to look effortlessly summery is to wear a white cutoff with a lightweight white shirt. Dress it up with a collection of metallic accessories.
Time To Heel — Unless you're Daisy Duke, wearing heels with your super-short cutoffs is generally a bad look. However, layering a spring jacket on top (and keeping your shirt baggy as well) helps maintain the balance and lets you confidently show off your gams.