Let's be real: most guys own one pair of shorts they actually like, and another four they keep "in case." We can do better.
The right pair of shorts does a lot of quiet work, it makes a polo look intentional, a linen shirt look effortless, and your whole summer feel less like a wardrobe compromise. Below are four pairs we keep recommending at Q.Contrary, each one solving a different problem. Pick the one that fits your week.
Greyson Wainscott Short — The Everyday Workhorse
There's a reason this one is a best seller. The Wainscott has the cleanest tailored silhouette in the lineup, a 9" inseam that hits right at the top of the knee (read: flattering on basically every guy), and a moisture-wicking performance fabric that breathes when the temperature climbs. It transitions seamlessly from a morning round to a casual lunch to errands you definitely need to run before dinner.
If you only buy one pair from this list, this is the one. Wear it everywhere.
Ballin Tech Short — The "I Have Plans Tonight" Short
If you've ever needed shorts that don't look like shorts, the kind you can throw on with a button-down for date night and not feel underdressed, the Ballin Tech is your answer. It's a dress-forward poly-blend tech fabric with 360° stretch, anti-crease construction, and shape retention so the silhouette stays crisp, even after a long day. (Ballin has been making men's pants in Canada since 1946, so they know what they're doing here.)
The structured waistband is the sleeper feature: it sits cleanly without rolling or buckling, which is genuinely flattering if you're carrying a little extra around the middle. Quick fit note: these run a touch small, so size up if you're between sizes.
9" inseam, dressy enough for dinner reservations, comfortable enough to wear all weekend.
Greyson Montauk Short — The Clubhouse Move
If the Wainscott is the workhorse, the Montauk is the upgrade. Greyson cuts this one from premium Italian fabric in a trim, slightly slimmer silhouette with an 8" inseam, a touch shorter than the Wainscott, which gives it a more refined, intentional look. The pink sky color is the kind of soft, easy hue that reads as confident without trying too hard.
Quick honest note on fit: it runs trim through the thighs and seat, so if you're built more athletic or a little fuller through that area, size up.
This is the pair that goes from the back nine to the clubhouse to a long lunch on the patio without changing.
NN.07 Gregor Linen Drawstring Short — The Vacation Short
This one is the easy yes. The NN.07 Gregor is 100% linen with a drawstring + elastic waistband, a relaxed casual fit, and a roughly 6.7" inseam. It's the pair you pack for a beach week and somehow end up wearing every single day, to breakfast, to the pool, to dinner with a linen shirt and leather sandals.
Dark army is the move because it's actually wearable beyond vacation. Throw it on with a white tee on a hot Saturday at home and you'll look like you tried, even though you didn't. (We won't tell.)
The pull-on waistband also makes it the most forgiving pair on this list when you've had the second helping of pasta.
Shop the NN.07 Gregor Linen Short →
So, Which Pair Do You Buy First?
If you only own a couple of pairs of shorts and want them to do everything: Wainscott. If you want shorts that look polished enough for a dinner out: Ballin Tech. If you spend real time on a golf course and want to graduate from the pro shop: Montauk. If a vacation is on the calendar (or you wish it was): Gregor.
Or, you know — just buy all four. Summer is short. Your shorts shouldn't be the limiting factor.
