How to Style Shorts

Date: May 1, 2024

Shorts season is officially here! It’s time to bring your favorite pair of cutoffs out of storage or the back of the closet and dress them up for a new season — or maybe add a few new pairs to the rotation to keep things fresh.

A woman with long brown hair wearing a green cap, a striped long-sleeve shirt, and blue drawstring shorts stands on a sidewalk. She is holding a red smartphone and has a gold watch on her wrist. This outfit pairs well with jean shorts.

When you were a kid, shorts were probably a foundational piece of your summer wardrobe. You could wear them with anything and everything, from oversized T-shirts (shoutout ‘90s kids!) to colorful tanks. Shorts are just as versatile once you’re all grown up, but they can be a little harder to style, in part because they’re so versatile. Can you really wear shorts with everything? We’re here to tell you that yes, you definitely can.

Ahead, learn what to wear with shorts of all kinds, from denim cutoffs to pleated shorts to longer-length styles like Bermuda shorts.

How to Style Short Denim Shorts or Cutoffs

The classic needs no introduction. Cutoffs are an absolute summer staple for people of all ages, whether they’re literal cutoffs from old jeans or the perfect pair of AGOLDE or Kut from the Kloth denim made to look like a vintage pair you unearthed at the thrift store.

A woman with curly hair is wearing a light beige knit sweater and black denim shorts while relaxing on a lounge chair outdoors. She has one hand resting on her face and the other hand on her lap, and she is wearing black sandals. This comfortable look includes stylish jean shorts.

Should cutoffs and jean shorts be tight or loose-fitting? Of course, this all depends on personal preference, but a slightly looser fit tends to be more comfortable and flattering, and is the perfect foundation for a plethora of jean short outfits. We know how annoying a pinchy denim short can be, so we make sure that every jean short we sell has the perfect leg opening — not too tight, not too loose, but juuuuust right.

There’s a reason the Kut from the Kloth Jane Short is one of our biggest bestsellers: it makes getting dressed so, so easy, which is exactly what you’re looking for in the summertime. The Jane Short comes in a variety of washes, like classic blue denim and a trendy gray shade; it’s made of the most comfortable stretch denim to move with you throughout the day; and you can choose between a raw edge cutoff style or a cuffed look to suit the occasion and your outfit. Agolde’s Parker Short is another effortlessly cool fan favorite in 100% cotton denim that molds to your body as you wear them, and the longer length gives you a little more coverage.

For a casual look

Shorts lean casual, so don’t overthink it! T-shirts, tanks, and sweatshirts are a natural match for low-key jean short outfits. A muscle tee feels edgy, while a mesh-y texture gives the classic cutoff a modern spin. When it comes to tees and tanks, a full- or half tuck feels the most modern.

Layers are key for those in-between days when it’s cool in the morning and warm in the afternoon. Wear your shorts with a simple, lightweight sweater or knit top and toss a jacket over the top; we love a light army green jacket or loose-fitting cardigan.

To dress up denim shorts

A tucked-in button down shirt always looks polished, especially when paired with a loafer or sleek slide. For a fun juxtaposition, pair your denim shorts with a super feminine ruffled top or printed blouse; it adds polish and prettiness to the more rugged denim. For a hippie vibe, grab a boho blouse and style with a brown leather belt and sandals.

Shoe-wise, anything goes — sneakers, flats, sandals, wedges, whatever!

How to Style Pull-On Shorts

Pull-on knit or chino shorts are another option for low-key looks if denim shorts aren’t your vibe. These have a sporty playfulness that makes them ideal for summer fun, so pair them with graphic tees or striped, colorful tops that lean into the casual vibes of the season.

How to Style Longer Length Shorts

We love a longer length short with a ladylike cardigan sweater. It’s a simple, chic way to elevate denim shorts, especially the bestselling AGOLDE Parker Long Short, which has a slightly longer length and inseam than a traditional denim cutoff.

A woman with long wavy hair is wearing a striped cardigan over a white tank top and distressed denim shorts, standing with her arms crossed. She is also wearing beige espadrille flats and leaning against a light-colored wall. This ensemble highlights a trendy way to style jean shorts.

Bermuda-length shorts are also making a comeback, and while they may give you pause at first, lean into the preppy vibes and pair them with country club-worthy pieces like a button-down Oxford shirt (half-tucked, of course!), or go tomboyish with a muscle tank and sneakers.

If you’re wearing a longer silhouette, stick to slightly cropped tops, lightweight sweaters, or slim-fitting tanks to balance the proportions and ensure you’re not drowning in fabric.