What to Wear for Labor Day and the Unofficial End of Summer

How to Dress for Labor Day with Huckberry

Need guidance when it comes to what to wear for Labor Day? Don’t we all.

It’s a holiday weekend that marks the end of summer and the transition into fall (slowly but surely). And it also means it’s likely time to hit the road for one last weekend trip or one more summer vacation. But, it’s not all fun and games. In addition to manning the grill and stocking up on craft beer — both hard chores, we know — you’re going to have to dress with comfort, relaxation and style in mind. It’s your lucky day — our great friends at Huckberry have all the gear you need when it comes to how to dress for Labor Day. Good luck out there.

Taylor Stitch Maritime Shirt Jacket, $148

Taylor Stitch THE MARITIME SHIRT JACKET in Sea Washed Indigo

The biggest task you might face this Labor Day? Dealing with an evening breeze that signals the inevitable, upcoming arrival of fall. Layer up accordingly with a durable, unfailingly cool Taylor Stitch shirt jacket in a stunning shade of sea-washed indigo that’s more than ready for Labor Day weekend (and well beyond). The perfect go-to piece for wherever the weekend takes you.

Almond Douglas Stripe Tee, $44


There’s no need to break out your best tailored wear for a casual weekend away. Instead, pack up (and wear) a classic striped tee in a handsome, neutral color. Layered under the M-65 jacket, it’s a stylish and easygoing way to nod to both summer style and classic style.

Howler Brothers Waterman’s Work Shorts, $60

Howler Brothers WATERMAN'S WORK SHORTS in Fatigue

Labor Day is all about mixing the high and the low — and that means you need shorts that can do it all. The Waterman’s Work Shorts from Howler Brothers are tough and durable — not to mention stylish enough to go from a Labor Day weekend hike to a barbecue or some patio brews without missing a beat.

Rancourt & Co. Carson Low in Natural Chromexcel, $300

Rancourt & Co. CARSON LOW NATURAL CHROMEXCEL in Natural Chromexcel

If you’re only able to pack one or two pairs of shoes for a quick weekend trip, might as well make one pair the visually interesting, dependable Carson Low from Rancourt. They nod to handcrafted American style and versatile looks in equal measure — a perfect fit for any Labor Day outfits.

Deep Blue NATO Diver 300 Automatic, $220

Deep Blue NATO DIVER 300 AUTOMATIC in SS Diver Black

Versatility in the way of accessories is also key. And if you don’t want to bother with packing multiple watches, might as well take a ridiculously tough — and very fairly priced — NATO strap watch that works in water and on land … with all-weekend style to burn.