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16 Stylish Guys On Their Favorite Summer Shoes

16 Stylish Guys On Their Favorite Summer Shoes

For Shoesday #3, I consulted some of the most tasteful fellas I know to create this list of warm weather footwear options.

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JAKE WOOLF
Apr 29, 2025
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16 Stylish Guys On Their Favorite Summer Shoes
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Welcome to Shoesday, a weekly column, sent every Tuesday, about shoes.

Now that some warm weather has finally, mercifully arrived on the East Coast, I thought it was the perfect time to compile a list of shoes that are specifically tailored to summer enjoyment—the kinds of footwear you’ll rock alongside your breeziest shirts, flow-iest shorts, linen-iest suits, and more. Now, if you’re a subscriber of this newsletter, then you know normally I’d just take this task upon myself and scour my favorite e-commerce sites to compile a selection of the best options on the market. I still might do that at some point, but this week I’m switching things up and trying something a little different by instead tapping the footwear wisdom of 16 of the most stylish guys I know, and whose taste I wholeheartedly trust.

That means below you’ll find the go-to summer 2K25 shoes of various writers, content creators, podcast hosts, and even designers, each of whom selected a pair of shoes that they personally wear, swear by, and ultimately think you’ll like too. Honestly, the best part about the list is that, while it is in my humble opinion just as useful as one I’d make myself, also completely different than anything I could have possibly cooked up. There’s everything from flip-flops to canvas kicks to luxury loafers in the mix, and even a couple of pairs of boots for those who prefer to give a big FU to the heat….anyway, let’s get to it, and enjoy!!!

This newsletter is ENTIRELY funded by subscriptions. I don’t use affiliate links, and all of these products are things I’ve endorsed and/or included because I actually like them, though in some cases I did not pay for them. Point is, your subscriptions are both extremely cool and very much appreciated. Thank you!

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The 6 Best Heavyweight Tees I Own

50 Style Items On My Spring-Summer 2025 Watch List

My 25 Favorite Sneakers For Spring-Summer 2025

And now for today’s post…

I Asked 16 Stylish Guys About Their Favorite Summer Shoes

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