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How to Dress for Warm Weather and Still Look Good

How to Dress for Warm Weather and Still Look Good

Look, let’s face it, summer is a hard time for anyone to look their best. It isn’t autumn when any old sweater, scarf, and jacket will do. And it isn’t winter, where you’re so bundled up in a coat, it doesn’t matter what you look like. No, summer has its own set of issues: humidity, worrying about having a good beach bod, and the dreaded swamp ass.

The one good thing about summer, from a sartorial perspective, is that there are many opportunities to dress for a specific occasion. Think about it, in the three-month span of summer, you could easily find yourself at the beach, on a boat, the best man at a wedding, or enjoying a much-needed holiday in Italy. It’s the full social calendar of the season which means I have the chance to update my wardrobe and try out a few new styles while I’m at it.

Here are a few ways that I’ve found to dress during the hotter days still ahead, but still feeling cool (both figuratively and literally).


Embrace the Wrinkles

A fabric that I came to love too late in the game is linen. God, what have I been missing? Just about any day of the week, you’ll see me in a pair of linen pants and a button-down (for the Alain Delon look, make sure the button-down is oversized). I stick with a fairly monochromatic color scheme when I’m wearing linen, giving me the flexibility to mix and match or create a warm weather uniform.

The only drawback of linen, of course, is the wrinkles. It’s something you really have to just embrace. They’re going to happen and even the crispest shirt will buckle and crease. It’s part of the charm and sure beats having to iron for a few months.

The Best Linens for Summer: Try Road to Nowhere’s Santos jacket and Tonga trousers for a casual uniform. Go ahead and pair it with some Sabahs in a bold color.


Who Wears Short Shorts?

If you didn’t answer that question with a resounding “Yes!,” then you’re doing it wrong. I look at my father’s yearbook and I enjoy the freedom they have in their short shorts. The sartorial mores of our time say that shorts should hit right around the knee, but I dare to dream big for my readers and think a five-inch inseam is just about right for anybody. It’s going to be strange at first, I’m sure, but a higher inseam has the added benefit of giving some length to your legs and giving the illusion of a more toned backside. Further, playing with proportions is a lot easier with a shorter short — baggier shirts tucked in the front for a Call Me by Your Name vibe, or a short-sleeve button-down for a more streamlined silhouette.

The Best Short Shorts for Summer: Aimé Sport Short; Todd Snyder Weekend Short; Patagonia Baggies


Sandals are Fine (with Exceptions)

You’ll find that, when it comes to shoes in the summer, I’m pretty flexible. I think, given the right conditions and outfit, just about anything goes. The stringent rule of sandals being “too casual” just doesn’t apply when circumstances are taken into account. What if it’s a beach wedding? What if all you have is a carry-on and you don’t want to be bogged down with dress shoes? What if you’re just hanging with friends at a bonfire? Sandals, clogs, slides — they’re all fine. It’s the flip-flop-loving crowd we have to be worried about. Anything that’s advertised as a BOGO deal at Old Navy just isn’t for you, my friend.

Nota Bene: Your sandal size and your shoe size won’t always line up. With, for example, clogs, your foot will naturally want to press more into the front of the shoe to add extra stability since there is no back or laces. Too loose, though, and you run the risk of chafing. I usually order my shoe size and a size up to ensure I have the best fit possible (only if it’s free shipping, of course).

The Best Sandals for Summer: Gauri and Co Woven Mules; Strange Paradise Slides; Birkenstock Arizona Essentials


Don’t forget the Accessories

With more clothes on, it’s easier to accessorize. You have a broader canvas to focus on. But that doesn’t mean you should forgo the extra step during the hotter months.

I’m particularly partial to ball caps/dad hats all summer long. I love them. They’re easy and often tighten up a look that one may otherwise mistake for my pajamas. My favorite is a classic Yankees hat. Unfortunately, I don’t know a lot about sports, so I avoid anyone who seems even the slightest bit interested in the logo on my cap.

Another option would be a kerchief or bandana. I love that small bit of dandyism that you can pull off with even just a plain t-shirt on. I’m fond of linen for the faded tonal colors, but some people look great with a silk option knotted casually around the neck. Look up about half the guys at Pitti Uomo this year — the only difference between them pulling it off and you is confidence.

Sunglasses are a staple, of course, but I recommend really investing in a good pair, especially ones that can be worn year over year. Try not to get too involved in trends, but also try to not stick with the standard aviator or wayfarer. I recently got a pair of Persols like those worn in The Talented Mr. Ripley, but these from The Reference Library were a very close second.

Don’t Stop There: I love a few pieces of jewelry, but try to keep it as simple as possible. I wear a couple of thin metal bracelets and a ring most days. But if I’m putting an outfit together, I may throw on a couple rings, like these signets from Atelier Domingo’s, or a necklace like this one from RÄTHEL & WOLF.

The Best Accessories for Summer: Persol PO3260S Sunglasses; Atelier Domingo’s Original Ring; Yankees baseball hat

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