#OOTD: This Is How to Wear Your New Favorite Jacket for Early Fall

If it feels wild to you to be talking about how to dress for early fall, rest assured that you’re not alone. Why, just yesterday, it seemed like we were talking about how to wear chukka boots for summer or even how to style your polo for spring. With all that being said, we’re standing now in mid-August, looking toward Labor Day and the gradual shifting of the seasons. Fall is my favorite time of year, and it’s quite the chance to make your men’s style essentials work for you. That being said, today’s #OOTD covers the kind of men’s gear you can start wearing right now, and then keep wearing on into October if you accessorize correctly (or heck, even longer than that if you live in a temperate climate).

It all starts with, as you’ll see below, perhaps the the best chore coat for men — the type of piece you can grab right now and wear atop a classic T-shirt, or have handy when it comes time to layer up with one of the best transitional shirts for men (as we’ve outlined below). Mix up layers as you please for that day hike, bonfire or to-go brewery visit, because the rest of the following picks (including workwear pants and packable waterproof boots) are ready to stand up to just about anything you’ve got in mind for late summer and into early fall. The full ensemble is below, so if you like what  you see, be sure to let me know the men’s gear essentials you’re picking up — find me on Twitter. Cheers!

A rugged chore coat and other men’s style essentials to move (slowly) from one season to the next.

Believe it or not, that brings us to the end of another #OOTD. Tough to believe, right? Hopefully, you’re a little more mentally prepared for the end of summer and the start of fall (sad, I know!). But that doesn’t mean you have to stow away your summer gear entirely — in fact, plenty of these pieces can easily qualify as early fall style essentials for September and October. That goes for the centerpiece of this outfit, a rugged jacket that’s easy to wear right now with lightweight pieces (a la that excellent rugged henley from Todd Snyder), as well as classic transitional pieces — hence, the classic men’s shirt shown above, too.

These pieces are rugged and adventure-minded (go off-trail or visit your cabin in style), all thanks to the Proof Rover Pants and some of the best men’s boots, a rugged and packable pair that doesn’t miss a beat in terms of style. Because who knows what plans you’ve got in store on or off the grid these days, I’m also recommending you snag one of the toughest shoulder bags to handle your everyday carry essentials. Naturally, to make sure you stay on time through it all, a stylish everyday watch belongs on your wrist, too. We’re not done yet, folks. No sir — because it’s still summer and all, some polarized sunglasses from Raen Optics are going to come in handier than you might think. While ending summer can be a bit of a bummer, it brings with it the promise of one of the best seasons for menswear: Fall! We’ll be right here at The Style Guide every step of the way to help you out.

 

#OOTD: How to Dress for Early Fall This Year

If it makes you jump out of your seat a bit to see the words “early fall” in a headline, know that I’m every bit as surprised by the end of summer as you. In that regard, we’ve been telling you all about the men’s style essentials to get you ready for the next season across these past few weeks, and today is no different. Our #OOTD focuses on the kind of gear you’re going to want to start slowly incorporating into your fall lineup, from a vintage-inspired chambray shirt to rugged leather boots and, simply put, the perfect pants to wear for early fall. This season is all about gear that can work with you in multiple situations. That’s why (as you’ll see), we’re incorporating a heavyweight pocket tee from our pals at Filson into the mix, seeing as you can wear it on its own during the day to grab a weekend coffee, then layer it up at night to grab cocktails at that new speakeasy in town. We’re also including a tough bag for your everyday carry, not to mention one of the best men’s watches you’ll find anywhere. Jumping into fall doesn’t have to be something you do all at once — mixing and matching the kinds of pieces that work in multiple seasons (and style situations!) is the way to go. So, ideally, this post can help you start to leave summer in the rearview mirror (sadly!) and look toward a crisp, cool, fun fall. Have questions for me on fall style tips? Reach out on Twitter.

 

Pairing a classic chambray shirt with a classic summer T-shirt — and classic leather boots. Get the idea?

  • The Shirt: Dickies 1922 Chambray Shirt, $190 — To be sure, we’ve been recommending pieces like a classic chambray shirt a lot lately — it’s the perfect layer to take you into the early part of next month, and this Dickies 1922 shirt is based on an old archival style. Utterly classic.
  • The T-shirt: Filson 8oz. Solid Pocket Tee, $55 — Leave it to Filson to craft a timeless pocket tee in a substantial fabric, perfect to wear on its own or layer underneath your new favorite shirt.
  • The Pants: Proof Rover Pants, $98 — A fitting hybrid between chinos and jeans is what this time of year calls for, and these might be the perfect pants to wear for early fall (and beyond). Easy to move around in, extremely breathable & also well-made.
  • The Boots: Red Wing Heritage Rover Boots, $269.99 — The key to moving this outfit from summer into early fall? Rugged leather boots from Red Wing Heritage, the kind that are still lightweight and versatile enough to wear with the Proof Rover Pants.
  • The Watch: Lum-Tec M84 Automatic Watch, $1,095 — Yes, we’ve been featuring this rugged Lum-Tec watch a fair amount on the blog as of late, all owing to the fact that it’s simply one of the best men’s watches on the market, and perfect for this outfit.
  • The Belt: Arcade Belt Co. Norrland Woven Belt, $38 — Finding a functional, rugged belt is no small task, but Arcade Belt Co. comes through with one of the best men’s belts we’ve seen — this is no flimsy, thin leather belt that you’d pick up by the check-out rack at a fast-fashion shop, mind you.
  • The Everyday Brief: Boarding Pass NYC Flight Brief, $199 — Thinking about taking this show on the road? Even if it’s just to knock out some work at your local coffee shop, this rugged, durable & yet refined flight brief is perfect for your everyday carry.
  • The Grooming Essential: West Skincare Recovery Cream, $55 — If you’re not yet acquainted with West Skincare, consider this your introduction. This is active skincare made for guys who need active recovery, and this cream in particular is designed to hydrate and restore skin.

Now, if you’re not feeling ready for early fall yet, well, consider this a helpful guide to get started. When you start out wearing a classic chambray shirt, especially the rugged Dickies vintage shirt above, you’re setting yourself up for success — it’s perfectly casual and versatile enough for summer and fall. The same can be said of the equally rugged Filson pocket tee, again the type of tee you can wear all on its own or under any shirt you’d like. Throw in quite possibly the perfect pants to wear for early fall, and you’ve got a winning base for an outfit that’s geared to sip on an Old Fashioned, crack open a cold beer or visit your local park. In fact, that’s where rugged leather boots from Red Wing Heritage can come in mighty handy — they’re extremely tough & versatile enough for multiple seasons. And when you accessorize with a rugged Lum-Tec watch, you’re keeping the outfit squarely in casual, go-anywhere territory. The only thing to do now? Grab your Boarding Pass NYC flight brief, accessorize with a functional, rugged belt and your everyday carry, then finish off your look with West Skincare’s Active Recovery Cream. OK, now who’s ready for early fall?