The Best Shorts For Men And How To Wear Them

Athletic, relaxed, or preppy, shorts are the quintessential summer staple that every man needs but most have difficulty finding. Shorts, given their casual reputation, can read messy and unrefined if done in the wrong fabrics and if the fit is off. Done well, however, and shorts will read polished, boosting your casual wear for summery looks done to absolute perfection. From short shorts to dressier versions, we take you through the best shorts for men to wear this summer.

The Perfect Fit

Over the last decade, shorts have got shorter. It’s traditional to lay the blame at Daniel Craig’s overexposed legs, ever since his Ursula Andress-esque stride from the sea in Casino Royale, sporting a pair of La Perla shorts that took their name a little too literally. But what’s suitable for James Bond on a Caribbean beach doesn’t translate well to a barbecue in Colchester.

“A length that grazes the bottom of the thigh is best,” says stylist Dan May, who has worked with the likes of David Beckham and Eddie Redmayne. “It’s the most flattering to any body shape and avoids cutting off the knee.” May also advocates a cuff at the bottom: “It offers the illusion of shortness without showing too much flesh.”

That low-thigh sweet spot is imperative even if you’re trying to cover up rather than show off. As with your upper half, acres of fabric only serve to draw the eye to precisely the thing you’re trying to divert attention from.

Even men with big thighs should opt for a slight taper to the knee, while the edges of your shorts shouldn’t extend beyond hip width, otherwise you risk boxiness that makes your calves appear puny in comparison. Ditto anything with cargo pockets – having things to carry is a problem easily solved by picking up a bag.

The Dos & Don’ts of Shorts

Shorts are most definitely not the easiest clothing piece to pull off. Whether you are someone who lives in shorts or prefers a pair of jeans, first things first, the fit is everything. Not all men have similar proportions, and the way something sits on someone else may not necessarily complement your body. So try on shorts before you purchase them. Strike an appropriate balance and find shorts that will be fitted, but not entirely constricting. Do not opt for shorts in cheap or ‘board-shorts fabrics for everyday wear – this will read juvenile and will not allude a mature aesthetic.

When to Wear Shorts


Shorts are the answer to relaxed casual looks. Team them with a chambray/linen button-down or a simple t-shirt. A pair of espadrilles or boat shoes will elevate your look and are a more appealing option to the typical thongs most gents tend to wear.

Smart Casual

It is important to realize that shorts need to be worn in the right context. We recommend thoroughly considering whether shorts would be ok for the smart casual event you are attending. If so, team chino-esque shorts with simplistic dress shirts and appropriate blazers or throw a lightweight sweater over your shoulders. Loafers and sneakers are great shoes for smart-casual events.

Sports Luxe

When it comes to perfecting sports luxe, comfortable shorts are integral, but the way they look should take maximum priority. It’s all about the way you adapt sporty clothing for everyday wear, so ensure your shorts are in basic colors for maximum versatility. Team your shorts with other staples, like rich-toned bomber jackets, white trainers, and novel baseball caps for a playful take on the sports luxe trend.

Different Types of Shorts

There are many short styles on the market, but we’ve selected three of the most versatile styles that should be a part of your everyday wardrobe.

Cropped Shorts / Short Shorts

The cropped short nods back to yesteryears with its retro vibes and shorter proportions. One of the most versatile short styles, the cropped short offers much in terms of flattering slimmer to medium body types and works terrifically for casual days and nights alike. Versatile tones are great, but don’t be afraid to experiment with a bit of color given this type of short is typically a casual staple piece. Team your short shorts with white trainers, espadrilles, and playful accessories like baseball caps, bright watches, and round sunglasses.

Tailored Shorts

The tailored short is typically reserved for smart casual looks. With their chino vibes and more inflexible materials, they are great for updating dressy casual looks for the warmer months. While they are stylish, tailored shorts are also great for practicality and will allow your legs to breathe. The main thing you should remember when opting for tailored shorts is to find them in versatile colors like navy, khaki, and beige, which will afford you a great deal of adaptability for your wardrobe.

Baggy Shorts

Your biggest responsibility when it comes to baggy shorts is to ensure that they are well balanced for your body type. Proportion is key, so ensure you know what works with your body, but more importantly for your height. Experiment with different fits and textures to ensure that the baggy shorts will be a flattering piece as opposed to reading clownish or dated. Preserve a much shorter length with your baggy shorts.

What are the most comfortable men’s shorts?

The most comfortable shorts will fit you well and have some stretch for freedom of movement. Even tailored shorts can be made with fabrics that have a stretchy design. However, if you are after a more casual look, it’s hard to go past a pair of sweat shorts made of soft, stretchy cotton for the perfect amount of lounging comfort.

What kind of shorts are in style for guys?

If you’re looking for an on-trend pair of shorts, show a little leg with a cropped pair, look more formal with tailored shorts, or embrace a chilled vibe with a pair of baggy shorts.