The list runs from olive hiking shorts in ripstop to black pleated shorts with a real crease, and the setting you’re dressing for decides which pair is yours: every cut is casual, and the shorter it is, the more casual it gets.
Daytime errands and beach trips take almost anything, while a barbecue or picnic needs chinos, linen or a relaxed blazer. Offices and formal events mostly rule shorts out, so check what your peers wear before you choose.
1. Cargo Shorts
Pockets are the whole argument for cargo shorts, and khaki is the safest color to carry them in. Keep the pockets close to empty, since a phone and a wallet on each thigh turn a clean line into a bulge.
A plain tee tucked in nowhere, white socks and gray sneakers keep it simple. I’d skip anything with extra straps or flaps.
2. Denim Shorts
Denim shorts earn their place by being the least fussy option in the drawer. Worn with a cream tee and white sneakers, distressed pairs look relaxed without trying hard.
Light fraying is plenty for me. Heavy rips read as a costume on a normal weekday, so I’d pick a pair with one worn-in look and let the tee stay plain.
3. Chino Shorts
Olive chino shorts do more work than their plain look suggests. Pair them with a black polo and you have an outfit that fits a waterfront lunch, a casual date or a backyard party.
Olive is my pick over tan because it hides wrinkles and pairs with black, white and navy alike. Keep the polo fitted through the chest, and the whole thing looks deliberate.
4. Athletic Shorts
On a train, in a white tee and black athletic shorts, comfort is the point.
Black is the version to own: it stays low-key, so a clean white tee makes the outfit look chosen rather than left over from the gym.
I’d keep these for errands, commutes and travel days. For dinner or a date, switch to chinos.
5. Bermuda Shorts
Knee-length Bermudas ask for a bit more care than shorter cuts, because the extra fabric can swallow a short frame. All black, with a long-sleeve top, keeps the line long and quiet.
The maker of this look added a lightweight V-neck sweater and leather sandals, which is a good variation for cooler evenings. Flip-flops are fine at home, but sandals look sharper out.
6. Loafers with Shorts
Brown loafers with light blue shorts give you the easiest way to dress shorts up without a tie or a jacket. White socks and a white shirt keep the palette clean.
I like a cap on top, since it stops the outfit from feeling too formal. Leather matters more than the shape: smooth brown leather looks intentional, while worn-out canvas slip-ons can look like an afterthought.
7. Linen Shorts
White linen drawstring shorts are the coolest thing you can put on in July heat. Linen breathes and stays light, and a striped button-down keeps the look from drifting into beachwear.
Wrinkles come with the fabric, and I’d accept them rather than fight them. A silver watch adds a little polish, and if you want one cheap upgrade, roll the sleeves to the forearm.
8. Short Shorts
Red short shorts with a floral white tee make a loud outfit, and they only work if everything else stays quiet. White sneakers do that job, so I’d leave the socks and accessories simple.
These suit warm days and men comfortable showing leg.
If that’s not you, a longer cut is easier. Keep the print on top only; 2 busy pieces compete.
9. Tailored Shorts
Black pleated shorts can pass for dressy, which is rare for the category. A white tank looks relaxed against them, and loafers in black and white tie the two together.
I’d choose a pair with a real crease and a clean waistband over anything stretchy. White socks keep the line light, and a fitted tank beats a loose one here.
10. Hiking Shorts
Olive hiking shorts are a quiet way to wear technical gear in town. They’re usually made from durable nylon or ripstop, so they shrug off rough use and don’t need babying.
Beige fleece and a brown beanie keep the palette earthy, which suits cool mornings. Pick olive over bright colors if the shorts will see daily wear, and swap boots for sneakers when the trail isn’t involved.
11. Shorts with a Polo Shirt
A navy polo with white shorts is about as safe as a summer outfit gets, and I mean that kindly. The contrast is crisp, and nothing needs explaining.
Choose a polo that fits through the shoulders and ends at mid-zipper of the shorts, not below.
Add clean, smart casual shoes in brown or white. Keep the white shorts spotless; they show every smudge.
12. Button-Down Layered Over T-Shirt
A cream button-down worn open over a white tee is the easiest layer for loose black shorts. It adds length and some structure without any extra heat.
Leave every button undone and let the shirt hang.
Black sneakers match the shorts and keep the bottom half simple. I like a tee a shade brighter than the shirt, so the layers stay distinct.
13. Casual Tee and Plaid Shorts
Olive plaid shorts are easier to wear than they look, because the pattern already supplies the interest. A plain black tee lets it stand alone, and black sneakers keep the bottom half from competing.
I’d pick a plaid with muted checks over a high-contrast one.
Olive reads close to a neutral, so the tee can be black, white or gray. Keep the print on one piece only.
14. T-Shirt and Baseball Cap
Cream tee, gray shorts, a baseball cap: an outfit this plain needs one thing that catches the eye, and blue sneakers do it. Keep everything else quiet and the shoes look chosen.
I’d wear a cap in a solid color, nothing loud, so the sneakers stay the accent.
Gray and cream sit close in tone, which keeps the whole thing calm. It’s a good errand-and-coffee outfit, and it takes about 30 seconds to put together.
When to Wear Shorts
Every pair of shorts is casual, and the shorter the cut, the more casual it gets. Save them for daytime outings, errands, beach trips and warm-weather events.
A relaxed blazer or a dress shirt can push them into semi-casual territory, which suits a barbecue or a picnic. Formal events and most offices stay off the list unless the dress code says otherwise.
Fabric matters as much as length. Running and athletic shorts often come with very short inseams, and they work outside the gym, but a wardrobe needs at least one pair that isn’t sports fabric.
I’d buy cotton or a linen blend, since the better material makes the same shorts look more considered.
Stick to well-fitted pairs in neutral tones or classic patterns, and they’ll work almost anywhere shorts are allowed.
Shorts Etiquette
Shorts are a great choice for sports, a beach vacation or tropical heat. In most other settings, they’re not the first pick.
At work, look at what your peers and higher-ups wear, then decide. An offsite retreat or a very casual workplace can make shorts fine; otherwise, skip them.
If you’re already known for pushing fashion boundaries, you can get away with it, but most men can’t.
My rule is simple: if you have to ask yourself whether to wear shorts, save them for another day.
Fit comes next. A pair that sits right on the waist and thigh looks intentional, while a sloppy pair undoes even the right occasion.
Traditionally, shorts have never held a prominent place among gentlemen in public, aside from wearing them to the beach or on the tennis court.
Frequently Asked Questions
What shorts are in style for guys?
Chino, denim and tailored shorts are the safest bets.
Olive chinos beat tan for me because they hide wrinkles and pair with black, white and navy. Denim works best with only light fraying, and tailored pairs look best with a real crease and a clean waistband.
How to style shorts professionally?
Choose tailored shorts with a crease and a clean waistband, then add a fitted polo or a button-down.
Skip stretchy fabric, and keep the palette simple, such as black pleated shorts with loafers. Shorts still don’t suit formal events or most offices, so check what your peers and higher-ups wear before you decide.
Do guys look good in shorts?
Yes, when the fit is right and the outfit stays simple.
A pair that sits properly on the waist and thigh looks intentional, while a sloppy pair spoils even the right occasion. Keep to neutral tones or classic patterns, and put any print on one piece only.
What shorts should a 45 year old man wear?
Olive chino shorts are the pick I’d make, worn with a fitted black polo.
That outfit works for a waterfront lunch, a casual date or a backyard party. Choose cotton or a linen blend over sports fabric, and keep the fit clean through the waist and thigh.
