Fall Style Guide: 6 Classics To Take You Into Fall


Fall is officially here, and depending on where you live it already feels like summer’s long gone. But early fall weather can be quite erratic, with brisk mornings, chilly nights, and afternoons that feel as though they’ve been pulled right out of summer. The key to dealing with this bipolar stretch of weather is layering, so yes, put away your warm-weather duds but don’t reach for your winter parka just yet. Below, I’ve rounded up my top 6 transitional pieces perfect for layering this fall that should keep you both warm and stylish in the months ahead.

The American Oxford

The oxford-cloth button-down, or OCBD for short, is perhaps the most ubiquitous article of clothing in all of menswear, and for good reason. No other shirt so perfectly straddles the line between formal and casual, and if I had to wear one shirt for the rest of my life, the OCBD would be it. The oxford-cloth button-down as we know it today was created by Brooks Brothers in the early 1900s, when the company adapted the collar–a design imported from across the pond and first utilized by English tennis players looking to keep their collars at bay during matches–to their preexisting oxford-cloth shirts (the “button-down” in OCBD actually refers to the collar design, not the shirt as a whole).


The fabric itself is made with a basketweave pattern where multiple warp threads are crossed over an equal number of undyed weft threads. The result is a cloth that is generally thicker than most shirting fabrics yet still incredibly comfortable against the skin, which is precisely why it’s a fantastic early-fall material (it’s also great for spring, winter, and cooler summer days). And it’s damn versatile, too–you can wear your OCBD to work or out to the bar, tucked or untucked, with or without a tie, and layered under a sportcoat or even a hoodie.

Uniqlo ($30)

Kamakura ($79)

Brooks Brothers ($95)

Gitman Vintage ($165)

The Grownup Sweatshirt

These aren’t the ratty oversized sweatshirts you’d wear to the gym. No, the sweatshirts I’m talking about are logo-free, soft to the touch, and cut as trim as any other sweater you might own. The arms and body should be fitted–not to be mistaken with tight–and the length should ideally hit somewhere around the belt line, though a little lower is perfectly acceptable too. Heather grey is a classic and versatile choice, but don’t shy away from colors like navy, olive, and brown. You can wear your sweatshirt over a tee paired with jeans, over your newly purchased OCBD and chinos, or layered under a denim jacket for those brisk fall nights.


Uniqlo ($20-$40)

Everlane ($40)

J.Crew ($75, $85, $128)

Todd SnyderXChampion ($98-$150)

The Denim Trucker 

If you’ve seen the movie Badlands, I don’t have to tell you how badass a denim trucker jacket can be. Simply put, it’s an American classic, and the thing that makes it so iconic is that it looks good on just about anyone. The key, once again, is to get the fit right–it should wear trim and close to the body, even if you’re on the heavier side. If your jacket is too baggy or the length hits far below the belt line, you’ve sized incorrectly. I recommend buying the raw variety (untreated and without any artificial distressing) with the purpose of breaking it in over time. Like a pair of jeans, a raw denim jacket will eventually fit like a second skin and fade in a way completely unique to you.


You don’t have to go much further than Levi’s ($78) to find the perfect trucker jacket. For those looking for a premium option, check out Imogene+Willie ($195) or the Japanese brand Big John ($295). If denim jackets aren’t your thing but you love the look of a classic trucker, check out Filson’s waxed tin cloth jacket ($230)–an ideal choice for those rainy days.

Heavy Cotton Pants

Denim is an obvious choice, especially if you opt for some of the heavier options (anything between 14 and 17 ounces is good). Dark, unadorned, and slim–meaning form fitting with a slight taper–are what you should be looking for. Indigo is a classic option, or you can try black or even grey for a little more variety. In my experience, two pairs–one black and one blue–are all you really need.


If you can’t wear jeans to the office, then go with cotton, but focus on heavier fabrics with interesting textures like twill, moleskin, and my personal favorite, corduroy. Corduroy is especially great because it adds an interesting layer of texture to any outfit, and the fabric is so soft you’ll feel like you’re wearing sweatpants at work.

Rogue Territory Stanton 16.75oz jeans ($245)

Uniqlo Corduroy Pants ($39.90)

Urban Jungle Hikers

Danner is a company out of Portland, Oregon known primarily for making hiking and work boots. They also produce a wide array of military and law enforcement footwear, built tough and made to take a beating even in the harshest of environments. The Danner Stumptown line takes that legendary build quality and wraps it in a more palatable, fashion-forward package.


The anchor of the Stumptown line is the Mountain Light model ($330), a design first introduced in 1979 and reproduced to spec. In terms of construction, they don’t disappoint. The upper is built around a single piece of leather, with the tongue folding over onto itself and closing the gaps one would normally find in a traditional pair of boots.  The interiors are also lined completely in GORE-TEX for extra waterproofing. They’re comfortable enough for fall, but they can easily take you through winter if you wear them with thicker wool socks. And if you ever wear out the nearly indestructible Vibram sole, you can send them back to the Danner factory for a little spa treatment.

Camp Socks 

Come fall, you’ll need some hearty footwear to contend with the impending chill. And with that, you’ll also need some socks. But don’t be boring.  Pull on something textured and patterned and with a color palette that goes beyond navy. Stripes? Sure! Fair Isle? Definitely! Even marled camp socks, like the colorful ones featured in our gallery, are a great choice for the fall months ahead. Plus, they’re thicker than your run-of-the-mill dress socks, and with some wool in the mix they’re sure to keep your feet nice and toasty.


Uniqlo (3 for $12.90, 4 for $12.90)

L.L.Bean ($19.95)

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Ilya is Worn & Wound's Managing Editor and Video Producer. He believes that when it comes to watches, quality, simplicity and functionality are king. This may very well explain his love for German and military-inspired watches. In addition to watches, Ilya brings an encyclopedic knowledge of leather, denim and all things related to menswear.