#OOTD: How to Wear the Best Men’s Chukka Boots This Summer

If I’ve said it before, I’ve said it a million times. The summer heat is no reason to relegate your chukka boots to storage. Why, just last month here on the blog, we talked about the best leather chukka boots you can buy for spring, the sort of pair that blends proper durability with style points and handmade craftsmanship. Those chukka boots, in fact, are back in a big way today as we explore yet another #OOTD, this one focused on, well the best way to wear chukka boots for summer. The key is keeping it light, breezy and casual-yet-cool, because the best chukka boots for men are the kind you can wear with mostly anything in your wardrobe, and just about anywhere (even to the office, once you check out the iconic dress watch in this ensemble). It helps that today’s featured chukka boots come from Veldskoen, which has a storied history of making chukka boots for hot weather.

When you don’t quite want to lace up canvas sneakers and it’s also far too hot for sturdy leather work boots, chukka boots are a great go-between. Especially if you’re spending time around and heading somewhere that requires a bit of polish and style (patio cocktails, anyone?), the best men’s chukka boots are just what the (style) doctor ordered. The supporting cast is packed with summer style essentials, including a stylish short-sleeve shirt from Huckberry. Tread carefully, select the best boots for summer and relish in the fact that you’ll have these Veldskoen chukka boots far past this season. Happy shopping, my friends.

The best way to wear chukka boots this summer

  • The Chukka Boots: Veldskoen Leather Chukka Boots, $179 — When the time comes to reach for dependable summer shoes, consider rugged-yet-lightweight, classic men’s chukka boots.
  • The Shirt: Wellen Hemp-Cotton Button Down, $68 — Keep things nice and breezy up top with this sustainable hemp-blend shirt from Huckberry.
  • The Lightweight Pants: Marine Layer Saturday Pants, $125 — These stylish drawstring pants look like chinos on the surface, but wear like comfortable sweatpants. Perfect for breezy summer days aplenty, and they’re possibly the best pants to wear with chukka boots.
  • The Socks: Mack Weldon AIRKNITx Ankle Socks, $18 — Get that “no socks” look without resorting to going barefoot. These comfortable ankle socks are the right accessory to keep you on your feet with functionality in mind. Oh, and Mack Weldon offers free shipping, too.
  • The Grooming Essential: Triumph & Disaster Coltrane Clay, $30 via UNCRATE — Shape your fresh, post-quar haircut with one of the best hair clays for men, folks.
  • The Watch: Shinola Runwell Leather Watch, $1,095 — Here’s the kind of stylish leather dress watch you can wear to the office and then to happy hour, or else to a cool-as-can-be summer party on the weekend, without missing a beat. The Shinola Runwell never fails, easy as that. 
  • The Sunglasses: Pacifico Optical Buckler Sunglasses, $195 — A sleek and on-trend #OOTD like this requires some of the coolest men’s sunglasses, like these round-frame shades in a crisp colorway.
  • The Everyday Carry: Mission Workshop 500D Drift Tote, $235 — Perhaps you’re not quite in need of a rugged tote bag like this one, but if you’re going to be out and about all day, it pays to pick up this much-loved Mission Workshop tote.

Does this #OOTD have you looking ahead to warmer days without much on your agenda besides getting another ice-cold beer at your favorite bar? Wherever you go — even if you decide to wear your new favorite chukka boots to the office — I’d say it’s well-suited to any style demand you can dream up. Start out with classic men’s chukka boots to set the tone (more casual than dress shoes, more polished than sneakers). Keep it breezy from there with a sustainable button down shirt from Huckberry, then throw on the best pants to wear with chukka boots to really drive home this effortlessly cool look.

Keep the details on point, too: A pair of comfortable ankle socks are a surprisingly underrated move when wearing chukka boots and straight leg pants (roll ’em up just a bit to show off some ankle). Shape your hair accordingly with one of the best hair clays for men, a nice way to put a bit of extra effort into this #OOTD. No matter where you go, a stylish leather dress watch is going to polish things up quite nicely with sharp looks, too. Elsewhere on the accessories front, some of the coolest men’s sunglasses will top this look off handily. And to haul your EDC picks, you know what to do: Grab the Mission Workshop tote and load it up at well. For expert, laidback-yet-cool summer style, you’ve just found the best men’s style essentials. Cheers, folks!


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