Editor’s note: For more posts covering #WTWT (What to Wear Today), click here.

Are you read for fall? Black suede bomber by Timberland. Slim dark denim by Mott & Bow. Glasses by Warby Parker. Boots by Thursday Boots.

There’s something in the air, isn’t there? A hint of a crisp breeze, maybe a rustle of leaves on the ground — yes? If you responded reasonably to either of these questions, then this is the blog post for you today on The Style Guide. The time between the often-oppressive heat of summer and the first snowfall can (depending on where you live) be rather long, or rather short. Either way, you need gear to get from point A to point B without continually relying on that stash of summer shorts and T-shirts. And given that fall is perhaps the best season for menswear, this is a time to fully embrace the transitional temperatures.

The ideal transitional outfit. Henley by Pistol Lake. Slim dark denim by Mott & Bow. Cotton rugby stripe socks by American Trench. Winston Herringbone watch by KOMONO. Boots by Thursday Boots.

The biggest key in making that transition comes in taking items you’d wear throughout the rest of the year — like a great henley — and repurposing those pieces alongside fall-appropriate textures (and colors, too). Take, for example, the short-sleeve henley you’d wear through the summer. Throw some long sleeves on that bad boy, look for a piece that’s been garment-dyed or incorporates some slight marled texture (Todd Snyder offers a pricey take on this variety) and you’re good to go in terms of casual weekend layering. It also does just fine underneath a sportier crewneck sweatshirt — budget retailers like Old Navy provide a great take on this menswear staple. Of course, no great henley would be complete without that essential fall layer — a terrific bomber jacket (Editor’s note: Look for a full rundown on key jackets for the season next week). Know that these pieces also work for the office, too — you can sub in a rugged chambray shirt  and fit right in depending on your office environment.

Of course, if you prefer a lighter top layer, a merino wool cardigan from the likes of JACHS NY (as discussed here) could do just fine, too. Heck, any of the sweaters discussed on this blog last week could work on their own if the temperatures aren’t too biting. And a trusty denim jacket is also always a solid piece to bridge that seasonal gap. But trying to push the envelope (within the reason) is what we’re all about. So if you haven’t given a great bomber jacket a look yet, this fall would be an excellent time to do so. The best bomber jackets are cut slim, with high armholes, relatively trim sleeves and a decently tailored fit through the body — essentially, just as your favorite fall blazer. There are a variety of fabrics and various takes on the bomber, all stemming from either military or athletic styles, but a crisp, fall-appropriate color (like the inky black seen above) and classic detailing never fails — particularly when it comes to this navy suede J. Crew bomber jacket.

A pricey but undoubtedly sleek take on the bomber jacket via J. Crew.

Cheaper options, like H&M’s Wool-Blend Pilot Jacket, are absolutely on the market, but you lose the unique texture of suede. And if you do go the suede route, paying a premium for higher quality is recommended. In fact, J. Crew appears to have that corner of the market covered with this buttoned suede bomber, too. Whichever route you do decide to take, it’s worth noting that any of the styles mentioned above could bring a sharp sportswear edge to something as dressy as a white Oxford, navy knit tie and grey chinos. And the nice thing about a classic jacket is that a quality piece in a neutral color will enhance any other classic staples you decide to stick with — say, that ever-reliable pair of dark denim you should have handy.

Before you drop lots of cash on a thick pair of selvedge denim, it’s worth exploring lower-priced retailers like Uniqlo and Old Navy for classic, well-fitting selvedge though. Mott & Bow’s Slim or Skinny denim offers a different take on the style, too — their jeans are built with a nice bit of stretch for lots of comfort and mobility.  In the spirit of jeans that’ll take a beating however, investing in a pricier (yet incredibly high-quality) pair from a retailer like Billy Reid is definitely an option, too. That same pair of dark denim can move seamlessly from the office to the bar when paired with crisp fall essentials — like that chambray shirt or that henley (if your office leans casual or creative). Perhaps the one thing that can really make or break a seasonal outfit is footwear, though. Fall is the optimal time to break out those boots from storage — and the options are numerous if you start out with a solid base (for example, a navy bomber jacket).

Get the most out of your transitional style with a grippy pair of tan suede boots. Pictured option by Thursday Boots. Patterned socks by Richer Poorer. Slim black jeans by American Apparel.

With, for example, a navy jacket, a great leather chukka boot is going to be an exceptionally versatile pick — although it all comes down to that jacket, as some might be against pairing a brown leather boot with a black suede jacket, or vice versa. Ultimately though, if the look is casual enough and the occasion calls for it — perhaps out at the bar with friends — that’s one rule it’s OK to break.  And some rugged black moc-toe boots as pictured earlier in this post can lend a rugged vibe to an outfit. To avoid any potential pitfalls though, an in-between tan suede captoe boot  (like that pair above from Thursday Boots) can really work wonders when it comes time to pull an outfit together. Don’t sleep on the brand’s new Chelsea boots, either. The tan suede matches well with black & brown leather belts, and although it gets a little close in the color wheel to a brown leather jacket, it’s a reliable option that works in a pinch with multiple outfits. And on the boot front, that’s perhaps one place it’s OK to skimp a bit if you throw down some cash on a great bomber jacket (case in point: H&M is even making a dark beige desert boot this season).

Given that multiple textures and potentially even variations on suede are incorporated into this look, playing it simple & classic on the #WatchGame front is advised. A stainless steel dive watch is a style essential that won’t fail you in any situation, be it dressy or casual, and brands like Invicta (as any reader of this site will know!) churn out affordable, reliable dive watches in bunches. By starting out with a neutral base, like a stylish and sleek bomber jacket, you give yourself leeway to work in other rugged-refined items for ensembles that can work in multiple situations, be it in the classroom, trekking through campus or heading out to your local watering hole. And no matter the situation, mixing and matching a few key pieces from the other three seasons should carry you well through this one.

How do you dress to transition through fall? What styles are you looking forward to bringing back out of your closet?