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.

• The Jacket: Flint and Tinder Chore Coat, $158 — Now, keep this tough chore coat in mind for when it starts to cool off once Labor Day passes. It pays off to be prepared, and the best chore coat for men is a perfect layer for early fall — thanks to Flint and Tinder for their work on this rugged jacket.
• The Denim Shirt: Buck Mason Double Weave Vintage Two-Pocket Shirt, $105 — Whether you choose to keep your Flint and Tinder chore coat on all day or feel like wearing this classic men’s shirt all on its own, Buck Mason has you covered with one of the best transitional shirts for men. Wear it from late summer into fall with ease.
• The Henley: Todd Snyder Made-in-LA Jersey Henley, $88 — To ease right on into early fall (crazy, I know!), pick up this rugged henley from none other than NYC’s own Todd Snyder. It’s one of the best short-sleeve henleys around, with easy layerability alongside your Buck Mason shirt.
• The Pants: Proof Rover Pants, $98 — Step out of summer and into early fall the right way — with some rugged men’s pants fit for the trail and bonfire beers in equal measure. The Proof Rover Pants, with their five-pocket construction and stylish array of colors, are some of the best pants for men.
• The Boots: LEMS Shoes Boulder Boots, $165 — Want waterproof boots that are packable, lightweight and made to take you through the seasons? You want some of the best men’s boots here.
• The Watch: Marathon MSAR Watch, $850 — Regardless of season, every guy needs a stylish everyday watch — if the watch in question just so happens to be an adventure-ready dive watch that looks great with waterproof boots, workwear pants and the Flint and Tinder chore coat? Even better.
• The Everyday Carry: Filson Ripstop Nylon Pullman, $250 — No matter what’s on your agenda heading through August into the fall, Filson is here for you with one of the toughest shoulder bags on the market. It’s got space for EDC essentials, work-from-home gear and plenty more.
• The Sunglasses: Raen Optics Wiley Polarized Sunglasses, $170 — Hey, there’s still time to admire many a late summer or early fall sunset out there, and you need to be wearing some of the best sunglasses for men to properly take it all in. These polarized sunglasses from Raen Optics take the cake.

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.