Style Suggestion: Here’s What to Wear for Labor Day Weekend

It’s summer’s last gasp, and it’s here already. Bring on Labor Day, and let’s start the never-ending quest as to what to wear for Labor Day weekend. Well, folks … that’s a bit dramatic, but your search ends today at The Style Guide. It’s a weekend that calls to mind any number of potentially tricky men’s style scenarios. After all, you’ve likely got to dress for a road trip … while also packing enough gear to wear to a weekend BBQ or head to the beach. We didn’t say it wasn’t a busy weekend, that’s for sure. It’s a great way to close out summer and look toward fall, and with that being said, it’s a weekend to approach with transitional style in mind. The gear you bring with you needs to toe the line between casual and laidback, yet appropriate for the situation. From manning the grill to stoking the bonfire, I think the below men’s style picks have something for everyone. That means we’re reaching for a ridiculously stylish Taylor Stitch shirt-jacket, plus an American-made T-shirt and classic khaki shorts — among other choice selections. I’ll let you be the judge of whether this outfit can work for you — if you agree, feel free to hit me up on Twitter. If not… keep it to yourself, ehh?

The Weekender Bag: Nisolo Leon Weekender — $397.98

Nisolo
A handsome, durable and super-stylish way to carry your favorite #menswear.

Is the Nisolo Leon Weekender expensive compared to lower-quality brands? Assuredly. But are you that much better off for ponying up the extra cash? Absolutely. A stylish weekender bag is yet another way to complement your stylish wardrobe — and with its burnished leather and quality construction, the Leon Weekender looks outstanding and is made to get better with age. That sounds to me like a pretty great way to pack up for Labor Day — and plenty of other road trips in the months ahead.

The Shirt-Jacket: Taylor Stitch Maritime Shirt Jacket in Sun-Bleached Indigo — $148

Taylor Stitch
Part shirt, part jacket — the perfect piece to wear on the road and once you’ve arrived.

With any gear — I mean, literally anything — from Taylor Stitch, you know you’re in good hands. With the rugged, casual-yet-versatile Taylor Stitch Maritime Shirt Jacket, that’s perhaps no more true. It’s an ideal piece to bridge the gap between summer and fall, crafted from 100 percent selvage Japanese indigo. That gives it a distinct look and a weight that’s just right for layering over a rugged henley or an American-made T-shirt at a bonfire — and that means you can wear it all on its own for weekend travel, too. In short, Taylor Stitch has outdone itself once again with the Maritime Shirt Jacket.
Frank And Oak

The T-shirt: Flint and Tinder Slub Tee in Dusty Field Grey — $38

Flint and Tinder
An American-made T-shirt that nods to a truly American holiday.

Labor Day is a holiday celebrating hard-working Americans in the labor force across the country — why not tip your cap to them with a stylish T-shirt that’s fittingly made in the States? From durable waxed trucker jackets to your new favorite Oxford — which should also be in your bag for the weekend — Flint and Tinder does it all. In fact, this Flint and Tinder slub tee  in a pleasingly faded dusty grey should fit right in with your rugged Taylor Stitch shirt-jacket for the weekend.
Timex
The Shorts: Taylor Stitch Maritime Shorts in British Khaki Linen Herringbone — $118 AND Flint and Tinder Breaker Trunk — $38.98

Casual men's shorts
A pair of shorts for night and a pair of swim trunks for the day. Nothing else to it.

Because we’re dealing with style scenarios aplenty across Labor Day weekend, you should prep and pack accordingly. If you spend the day at the beach or the pool, break out the affordably priced, well-made and durable Flint and Tinder Breaker Trunk in a go-anywhere shade of dark grey. The tailored fit helps the Breaker Trunks wear more like shorts for day trips to a lake or the beach. And for the rest of the time — backyard BBQ or bar trip alike — Taylor Stitch delivers on both versatile style and a unique fabric blend with the Maritime Shorts in a standout shade of British Khaki. It looks to me like these are the perfect shorts to close out summer, ehh?

The Footwear: SeaVeees Hermosa Plimsoll Regatta — $69.98

SeaVees
From the custom-dyed upper to small details like waxed cotton laces, SeaVees has crafted a pair of sneakers fit for the last bit of summer.

When you need style that’s simple and effective, you should reach for a sneaker like the SeaVees Hermosa Plimsoll Regatta. The timeless silhouette of the SeaVees Hermosa Plimsoll channels the kind of laidback, go-anywhere vibe you need for Labor Day. The Hermosa Plimsoll also features a custom-dye herringbone textile upper and waxed cotton laces — two touches that upgrade it considerably over your average pair of sneakers. When it’s time to hit the beach or the pool, just kick ’em off — SeaVees sneakers are practically made for it.

The Socks: Arvin Goods No-show Socks (Three-pack) — $30

Arvin Goods
Sustainably made no-show socks crafted with style in mind.

Never one to skip out on the details, stylish no-show socks are going to be an essential as you pack up this Labor Day weekend — particularly if you’re bringing easygoing sneakers. Available with simple color combos and blocked designs that won’t look half-bad after you’ve slipped off your sneakers, Arvin Goods makes the brand’s no-show socks with sustainability, style and fair pricing in mind. Another brand that’s tailor-made for Labor Day, ehh?

Greats

The Watch: Ventus Caspian C-01 Brass Watch — $299

With a case that’ll patina over time and a black canvas strap, this is a durable weekend watch.

When a weekend calls for a little bit of everything — from beach time to pool time to grill time — you need a stylish casual watch that’s up to the task. The rugged, durable and uniquely crafted Ventus Caspian C-01 Brass Watch is your pick, fella. The brass case on the tough Caspian C-01 Watch is designed to patina over time — that’s a good thing, because this timepiece can stand up to adventures aplenty. The black canvas strap and 100-meter water resistance add another dimension of functionality, too. In summary: Definitely bring this watch with you for Labor Day.

The Sunglasses: Steven Alan Bristol Sunglasses in Brushed Gold — $148
Steven Alan
Throwback vibes make for a distinct and versatile pair of sunglasses.
Make no mistake, you don’t want to be caught away from home without a pair of stylish sunglasses. And with their retro-inspired design, versatile shape and unique gold finish, these Steven Alan Bristol Sunglasses are perfect for laidback beach days and day trips this coming Labor Day weekend. And the good news? The Bristol Sunglasses will look just as great for Labor Day trips in years to come as they do now.
Grooming Essentials: Harry’s Essential Travel Shave Kit — $49.98
Harry's Shaving
All the gear you need to get the perfect shave while on the road.
Another thing you don’t want to leave behind? Your toiletries. And if you’re a guy who likes to keep his scruff maintained — as you should be — the easy-to-use, travel-friendly Harry’s Essential Travel Shave Kit bundles everything into one package that’s, well, essential. Trust me: Don’t leave home without it.

Florsheim

The Ballcap: Huckberry Explorer’s Cap — $38
Huckberry Explorer's Cap
Grab this ballcap, toss it on and hit the road — it’s perfect for travel and Labor Day weekend particularly.
Among #menswear picks you see pop up consistently on this site, the Huckberry Explorer’s Cap might top that list. Maybe it’s the fact that these vintage-inspired ballcaps are so well-made and subtly stylish, yet it’s the perfect spring and summer … and fall … and winter accessory to me. When you want to keep the sun off your face this Labor Day weekend, there’s not a better ballcap out there to grab.
The Essential: Orange Vessel Co. Stoneware Growler — $69.98
Stoneware Vessel Co.
Perhaps the best way to transport your favorite beer — and keep it fresh and flowing at your destination.
Now, is beer a “must-have” essential in the way that the Huckberry Explorer’s Cap or a Taylor Stitch shirt-jacket might be? Surely not. And if you’re hopping on a plane this Labor Day weekend, well, this Orange Vessel Co. growler will have to stay behind. But if you’re making the trek to a friend’s house and can spare some room in your ride? This durable growler can more than handily help you transport your favorite craft beer.
Gifts for the Host: Brooklyn Slate Company Slate Coasters — $27 AND Spiegelau IPA Glasses, Set of Four — $32
Spiegelau
Two gifts that pair nicely with one another — oh, and great beer.
Yet again, let’s keep in mind a golden rule of travel: Always bring a gift for the host. Or in this case, gifts. And hey, there’s some beer in the mix again! Brooklyn Slate Company makes a coaster that’s, dare I say it … stylish and rugged. And Spiegelau crafts some of the more unique glassware in the beer world — bring along the Orange Vessel Co. growler and fill it with your favorite IPA. Those IPA glasses will do the rest of the work.

Ready for some fun in the sun — and a few choice brews — this Labor Day? I know I am. And I hope you’ll be packing and wearing the best men’s summer gear for the occasion. I can’t recommend easily wearable pieces like an American-made T-shirt and a rugged Taylor Stitch shirt-jacket enough — from the beach to the bonfire, both layers absolutely work. Accessories like the Huckberry Explorer’s Cap are definitely critical, as is a rugged casual watch and the right weekender bag. It’s also critical to remember stylish shorts, and luckily for the both of us, the Taylor Stitch Maritime Shorts fit the bill nicely. Packing up men’s grooming essentials is pretty critical when it comes to staying fresh — let the Harry’s Essential Travel Shave Kit do the work for ya. I’d definitely be remiss if I didn’t remind you to bring along stylish sunglasses (preferably something retro-inspired like the Steven Alan Bristol Sunglasses). Lastly, don’t leave home without your favorite brew — the Orange Vessel Co. growler helps check that box. How will you be dressing for Labor Day? And what do you think of the above picks?  Let me know via The Style Guide Facebook page!

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