The List: Buy This Rugged Gear to Make the Stylish Transition into Fall

Simply stunning suede chukkas that should be on your list for early fall.

Ahh, yes — here we are. Right before Labor Day weekend, staring down the end of summer and looking toward early fall. What’s a guy to do? Easy. Shop for men’s style essentials like a tough camp shirt, a rugged long-sleeve henley, a  classic men’s Oxford shirt and stylish suede chukka boots. Then, wait for your closet to refresh almost instantly. OK, not quite. But the point is that the pieces you buy now are going to make all the difference in getting you ready for the season ahead. And if I were you, the first purchase I’d start with? Pre-funding the stellar Taylor Stitch Chukkas in Chocolate Weatherproof Suede, as seen above (and below). Good luck out there.

Taylor Stitch Chukkas in Chocolate Weatherproof Suede — $248

Simply beautiful suede chukkas for early fall.

Our friends at Taylor Stitch always up the ante when it comes to dependable style on all fronts — these handsome, functional Weatherproof Suede Chukkas should be a go-to pair of stylish fall boots with everything from a charcoal herringbone suit to a classic chambray shirt and indigo denim.

Taylor Stitch Everyday Blazer — $277.98

Taylor Stitch

The year-round blazer you need, made from fall-friendly suiting wool.

Made from year-round suiting wool in the tailored-yet-not-tight fit for which Taylor Stitch is known, the Everyday Blazer is handsome & versatile, wearable with tan chinos or dark denim. Pair it with the Weatherproof Suede Chukkas above for A-plus style from head to toe.

Frank And Oak Dylan Slim Raw Selvedge Denim — $119

Super sharp, slick denim from a Canadian menswear stalwart.

Frank And Oak stays on the cutting edge of things with monthly product drops, and that’s certainly the case with their recently revamped denim line. The crisp and clean Dylan Slim Raw Selvedge are the perfect pair of jeans to wear to your next rock concert.

Flint and Tinder Staywax Camp Shirt — $168

Just one of the color options in which you can pick up the durable Staywax Camp Shirt.

The extraordinarily tough, durable and stylish Staywax Camp Shirt is the quintessential fall shirt — easy to layer over everything from a slub tee to a long-sleeve thermal henley. Add broken-in denim and tough leather boots … bingo.
Roark Revival 12.5oz. Travel Stretch Denim — $67.98

A pair of crisp, well-cut indigo denim — nothing more, nothing less.

OK, so you’ve got your tough outer layer for early fall — what about a stylish pair of classic men’s denim? That’s where Roark Revival enters the frame — the brand’s Travel Stretch Denim is comfortable and well-fitting, perfect for a fall getaway.
Rhythm Vintage Stripe T-shirt — $34
Bespoke Post

An easy-to-wear T-shirt in a shade befitting of early fall.

Is there such a thing as a stylish T-shirt that’s uniquely suited for early fall? In the case of the Rhythm Vintage Stripe T-shirt, well … yes. The rich stripes are vintage-inspired and ready to layer under a charcoal Oxford with dark denim.

Frank And Oak Jasper Oxford Shirt in Dark Red — $39.50

Nothing better than a fall-friendly Oxford, perfect for layering with a rugged crewneck sweater.

OK, you’ve got your stylish T-shirt on lock, so the basics are taken care of. The Jasper Oxford Shirt from Frank And Oak exudes  casual-yet-elevated style — the Dark Red color is ideal for wearing with the aforementioned Travel Stretch Denim and the beautiful Weatherproof Suede Chukkas from Taylor Stitch.

Timex x Todd Snyder Military Watch — $138
Timex x Todd Snyder

A striking casual timepiece perfect for wearing with your favorite jeans and your favorite boots.

The ongoing Timex x Todd Snyder partnership never disappoints — take the handsome Timex x Todd Snyder Military Watch, a fast-selling, stylish casual timepiece that’ll take you into September and beyond in serious style.
Bellroy A5 Work Folio — $199

A slim, stylish work folio to organize your essentials.

Stepping into a new season is all about staying organized — this, the Bellroy A5 Work Folio can help you get ready for Q4 (or whatever you might be working on) in style. Truly, it’s an everyday carry essential.
House99 Truly Brighter Eye Balm — $26

The little details, even in grooming, make a difference. Well-done, Mr. Beckham.

House99, the line of grooming gear from sporting legend and style icon David Beckham, can absolutely help with keeping your grooming rotation tight and well-stocked.. I’ve been testing the Truly Brighter Eye Balm across these past few weeks, and it reduces puffiness and adds luster — a winning combo, in short!
Grayers Campesina Double Cloth Thermal Henley — $48.98

Providing an ideal mixture of comfort and warmth, this henley should be a fall go-to.

So, what exactly are you going to wear under a rugged outer layer like the Flint and Tinder Staywax Camp Shirt this fall? Easy. A classic henley, much like the layering-friendly Campesina Double Cloth Thermal Henley from Grayers.
BREDA Visser Watch — $90

Dressy, classic and still easy enough to wear with a T-shirt.

For those who favor a stylish leather watch with some polish, the BREDA Visser Watch is an affordable alternative to add to your watch collection. You can wear it everyday — especially with a classic Oxford. Speaking of …
Flint and Tinder Garment-Dyed Oxford — $98
Flint and Tinder

A rich, fall-ready color sets this Oxford shirt apart.

Another Oxford?/ You betcha. If ou’re going to transition into fall, you’re going to need menswear essentials that look the part — like the richly crafted Flint and Tinder Garment-Dyed Oxford, an easygoing shirt made for everything from blazers to crewnecks.

Knickerbocker Mfg. Co. Olive Watch Cap — $40

A warm watch cap that you’re going to need sooner than you think.

It’s going to be chilly before you know it — sadly, that is. However, the simple-yet-stylish Knickerbocker Mfg. Co. Olive Watch Cap is one way to be prepared ahead of time.
Now then … who else is ready for the start of fall? I know I am. Hopefully, these versatile men’s style essentials get you thinking about the changing seasons. For me, something like the Everyday Blazer from Taylor Stitch is the perfect way to step into (slightly) different weather. And for my money’s worth, I’d say you can’t go wrong by picking up the Weatherproof Suede Chukkas to amp up your fall footwear rotation. Have other thoughts? Hit me up on Twitter. Thanks for reading! 

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