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A couple of weekends ago, I was in New Orleans, where I found myself at a bar called The Swamp.
Let me tell you: the swamp creatures were out. The drunkest, barely-21-year-old college kids were swarming the premises (or more accurately, swaying around the premises and filming themselves dancing on TikTok). After realizing we were the oldest patrons there, my group and I swiftly maneuvered our way out of the crowd of intoxicated children, but not before noticing that all of the men there were dressed the same.
It was polo shirts paired with tight, light khaki short shorts as far as the eye could see. I have been a proponent of short shorts for years, so I’m not taking issue with the length here, but rather the awkward tightness of the bottoms and the outfit as a whole.
Now, I’ll cut the youngins some slack here. Whether it’s due to lack of funds or lack of inspiration (if your peers are all dressing the same, why ostracize yourself?), they’re probably wearing the same shorts their mom bought for them in high school. However, I have seen many a grown man wear a khaki short to barbeques, tailgates and summertime dinners. It’s the article of clothing many men gravitate towards for casual-to-semi-formal warm-weather get-togethers. Unfortunately, your sad, beige, uninspired khakis still look boyish to me.
Instead of channeling SEC frat boy this spring, ensure you’re elevating your warm-weather ‘fits with a pop of color and a touch of retro bagginess. I prefer a Patagonia baggie or a loose, drawstring pull-on short over the rigidity of a thigh-hugging khaki. Throw on a crewneck sweater or a crinkly button-down, and you’re good to go.
This specific vibe I’m trying to get you to cultivate is maybe best exemplified by the popular Instagram account @lostjcrew, which posts pages from old J. Crew catalogs from 1983-1997. The page is rife with retro-style inspiration and a time capsule for editorials before the age of the internet. Think dashingly handsome models doing preppy activities like skiing in knit sweaters, walking barefoot on the beach in J. Crew’s iconic rollneck and sailing in a pair of white and blue-striped shorts.
Nearly every look is simple. Take this man hauling what looks to be wooden lacrosse sticks in a plain, grey long-sleeve shirt and a pair of very green shorts that hit on the upper thigh. Or these three gentlemen standing on a pier observing a landing seaplane in rugby shirts and casual shorts.
Are these particularly revolutionary outfits? No. But it is a classic look, one that maintains your comfort while making you look put-together.
Ditch the khakis this spring and summer, and peruse a few of my favorite short options right now below.
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