There’s a moment every year: usually sometime between the first real warm Saturday and the sniff of Masters week, when you realize it’s time. The pants get folded, pushed to the back of the closet, and the shorts come out of hibernation. It’s not just a wardrobe shift, it’s a mindset change. The days get longer, the calendar fills up with golf, patios, and impromptu dinners, and suddenly getting dressed should feel easy again. Shorts season isn’t about cutting corners. It’s about dialing things in without overthinking it.
The problem is that most guys still treat shorts like an afterthought. Baggy, too long, too technical, or just plain forgettable. They get ‘cheap’ options. However, done right, a good pair of shorts carries the same weight as a well-cut pair of trousers. Clean lines, the right length, and the right fabric—and you can move from a morning tee time to drinks without missing a beat. Shorts season isn’t about dressing down. It’s about getting the details right when everything else gets simpler.
Here is my rotation:
From top left:
1. Pennbilt Club Shorts: These have become my go-to shorts – they are easily dressed up and look great as a casual option. Just a touch of stretch has these cotton bad boys performing like technical cousins. The new 7″ option is good…but feel free to hem ’em up to that 5-6″ inseam power play.
2. Holderness & Bourne Harwood Shorts: An absolutely fantastic pair of golf shorts. They run a little slim, so it may be good to go a size up. Standard 8-9″ inseam…you know what I’m going to say.
3. Patagonia 5″ Stand Up Shorts: They are back, and they are legit. Maybe a touch thinner fabric than their older (vintage) brothers, but they are just what the doctor ordered.
4. Johnnie O Melrose Cotton/Linen Shorts: A GREAT option to have. Dress these up with a solid polo on the golf course or a date night, or cut them off and wear them beaters all Summer long.
5. Duck Head Gold School Chino Shorts: Your middle-80%-ers. They work with everything, and the new color options (pink!) are so cool. The price point makes these a no-brainer.
6. B.Draddy Zac Shorts: These are utility shorts. Get those inseams where you want them, and they are great for the golf course (original intent), for the park with the boys, or for jumping in the pool. The quick-dry material performs. And performs well.
7. Sid Mashburn Field Shorts: The dressed-up version of the Stand Ups…I’ve been wearing these for as long as Sid has been open, and I still have a few pairs in the drawer. They are built like tanks and look cool in almost every situation. The deeper the fade, the cooler the look.
8. Lululemon ABC Golf Shorts: Golf Go-To shorts. They have a little more structure and hold up incredibly well.
9. Peter Millar Crown Weekend Shorts: Beaters…for those occasions where you need something nicer than baggies, but don’t want to wear a belt. Hack: These are my driving shorts…great for long hauls down to the beach.
What did I miss?
