The 11 outfits run from plain tan chinos and a tee to a matching short set, and from sneakers to loafers and clogs.
What you’re doing that day picks the one to wear: a casual dinner calls for a button-down or a beige henley with loafers, a weekend errand run suits a graphic tee or black drawstring shorts, and a cool night calls for a gray sweater.
Fabric matters as much as the outfit, since cotton, twill and denim each wear differently by 2 p.m. in July.
1. Chino Shorts
Tan chino shorts are the safest pair a man can own, and I’d buy them before anything louder. Tan goes with navy, white, olive and gray, so one pair covers most of a week’s tees and shirts.
A solid tee and clean white sneakers are enough. If a plan has a table and a tablecloth, swap the tee for a button-down and leave everything else alone.
2. Denim Shorts
Light-wash denim shorts bring a worn-in, rugged look that suits a weekend afternoon better than an office-adjacent lunch.
A single pop of color from the shoes works when everything else stays quiet. Skip a denim top with them unless you want a full Canadian tuxedo, which is a lot in summer.
3. Everyday Shorts
Two men, two shirts, two pairs of shorts, and nobody is trying hard. That is the appeal of an everyday pair: they work for drinks on a ledge, a walk through the city or a casual dinner.
Pick a short-sleeved button-down in a solid or a small print and wear it untucked.
Mid-tone shorts in a neutral shade will mix with most of what is already in your closet, so buy one good pair before a third or fourth.
Relax, pal—you don’t have to keep up with every manufactured menswear micro-trend. Instead, embrace the fact that the state of shorts today is, well, whatever you want it to be.
— GQ
4. Cargo Shorts
Black cargo shorts with side pockets give you somewhere to put your phone, keys and wallet, which is the whole reason to wear them. Black also hides the bulk better than khaki or olive does.
Pair them with a plain white tee, as above, and keep the pockets mostly empty so the shape stays clean.
I’d choose a pair that sits at the knee or just above it; anything baggier and longer starts to look like a costume.
5. Shorts and Low Top Sneakers
Black drawstring shorts, a black tee, white socks and white low tops make a two-color outfit that needs no thought. The white at the feet is what keeps all that black from looking flat.
Wear crew socks that show just above the shoe, as here, and keep the sneakers clean; scuffed white ruins this look fast. It works for errands, the gym commute and an easy day out.
6. Short Sets
A matching short set removes the guesswork: a black tee and shorts in the same fabric, finished with white sneakers, and you’re dressed in about a minute.
The shared color makes you look taller and more put together than separates tossed together.
I’d wear the set as a pair only occasionally, and break it up on other days. The tee pairs with jeans, and the shorts with a white tee, so one purchase gives you three outfits.
7. Graphic Tee and Shorts
A graphic tee works best when it is the only loud thing on you. White with a bold print, black shorts and a black cap keep the colors tight, so the shirt does the talking.
Choose a print you would still like in a year, and keep the shorts plain. Crew socks and chunky sneakers finish it, and none of it asks much from you on a weekend.
8. Button-Down Shirt and Shorts
Light blue and beige are a quiet pair, and a button-down turns plain shorts into something you could wear to a casual lunch or a store run. White sneakers keep it clean.
Wear the shirt untucked with the sleeves rolled to the forearm or just past the elbow, and keep the shorts a shade or two lighter or darker than the shirt, never the same.
I’d pick this over a tee whenever the plans include anyone you want to impress a little.
9. Patterned Shorts and White Tee
Let the shorts carry the pattern and keep everything above them plain. A white tee pairs cleanest with light blue printed shorts, because nothing competes with the print.
White sneakers match the tee and tie the outfit together.
A cap is optional, but I like one on a sunny day. Choose a small or soft print over a busy one, since it is easier to repeat through a summer.
10. Long-Sleeved Henley and Loafers
A beige long-sleeved henley with navy shorts is a calmer, older take on summer dressing, and loafers push it closer to smart casual than beach. Brown leather loafers suit the warm beige.
Push the sleeves to the forearm and leave the placket open a button or two.
I’d skip socks or wear low ones that don’t show. It suits cooler evenings, dinners and anyone tired of tees.
11. Sweater and Clogs Outfit
A textured gray sweater over a white tee is how I’d wear black shorts when the weather turns cool. The tee collar shows at the neck, which breaks up the gray.
Slip-on clogs in a neutral tone make the look relaxed and easy to put on.
Keep the shorts plain and fitted, not baggy, so the sweater is the focus. It’s a good evening outfit for a cool night out.
Choosing the Right Materials
Fabric decides how a pair of shorts feels by 2 p.m. in July, so check the tag before the color.
Cotton is the dependable default.
It’s soft and breathable, and it works across seasons, which is why chino and tailored shorts are usually cut from it. Wear cotton with Oxford shirts or polo tees and it looks put together without effort.
Twill is cotton with more structure. It holds a crease and drapes a little better, so it suits casual outings and everyday errands where you want some shape.
Denim is the most versatile of the three. It goes with graphic tees, tanks and lightweight button-ups, and it carries from daytime into the evening.
If I could own only one, I’d pick cotton twill for its balance of comfort and shape.
Color Coordination
Start simple: pick shorts, shirt and shoes in the same shade family. That keeps the outfit reading as one idea instead of three.
White and gray tees pair with almost any color of shorts, so they’re the safe starting point.
Navy and black sharpen casual chinos, while tan and beige warm up lighter shorts. Pastels lift a summer look, but leave everything else neutral.
Brown leather sandals and white sneakers cover most situations. Skip dress shoes and wool blazers, since both fight the casual base.
A striped polo adds a little pattern without much noise.
If you want to skip the thinking altogether, try a matching top-and-bottom set. It shortens your morning, and you can spend the saved time on the details, like a belt or a watch.
Frequently Asked Questions
Can shorts ever look dressy?
Yes, tailored shorts in a solid neutral like navy, stone or charcoal work with a crisp polo or a linen short-sleeve shirt. Leave out cargo pockets, heavy denim and elastic waistbands, since they pull the outfit back toward casual.
What colors work best with shorts?
Keep the shorts, top and shoes in one shade family so the outfit reads as a single idea.
White and gray tees go with nearly any shorts color, navy and black sharpen chinos, and tan and beige warm up lighter pairs. Pastels brighten a summer look if everything else stays neutral.
What shorts should a 45 year old man wear?
Chino or tailored shorts with the hem just above the knee (a 7–9 inch inseam) are the safest choice at any age.
Tan chinos mix with navy, white, olive and gray, so one pair covers most of a week. Wear them with a polo, a short-sleeve shirt or a plain tee, and skip anything baggy or oversized.
What to wear with shorts?
A solid tee or a short-sleeve button-down worn untucked, plus clean white sneakers, handles most situations.
Brown leather sandals also work, and loafers push the look toward smart casual. Skip dress shoes and wool blazers, since they fight the casual base of shorts.
What is the current trend for men’s shorts?
Shorts now cover far more than gym wear: chino, denim, cargo, tailored and patterned pairs all work.
Light-wash denim gives a rugged weekend look, and matching top-and-bottom sets make dressing quick. Whatever the style, fit comes first and color second.
