Key Brands:
Polo Ralph Lauren, Brooks Brothers, J.Press, Gitman Bros., Beams Plus, Bass

Key Pieces:
Navy Blazer, Varsity Jacket, Rugby Shirt, Oxford Shirt, Penny Loafer, School Sweater, Chinos (in Khaki or Neutral Color), Knit Tie

How to Wear This Look:
The “Back to school” vibe doesn’t only have to apply to those hitting the textbooks. A seasonal staple all on its own, there’s a decades-long legacy when it comes to the well-educated aesthetic. Engineered by the well-heeled students roaming the halls of America’s Ivy League institutions in the mid 20th century—but preserved by detail-obsessed Japanese fans—the style is a blend of casual tailoring and school-themed gear. While it’s unlikely that most modern men will consider switching up their entire wardrobes to soft-shoulder suiting, there’s aspects that should fold into most wardrobes quite nicely.

For some easy wins, consider swapping sneakers for a pair of loafers, a pair of chinos for your daily jeans, scooping up a vintage college sweater (bonus points if it actually is your alma mater) and trading your denim jacket for a varsity jacket or blazer. You may not have that Ivy League degree, but you can certainly dress like you do.

Key Brands:
Shorts: Patagonia, Stone Island, Supreme, Nike, Eric Emanuel, Prada

Hoodies: (Including, but not limited to) Champion, Supreme, Palace, Off-White, Stone Island

Key Pieces:
Statement Sneakers and… well, Shorts and a Graphic Hoodie

How to Wear This Look:
Before you roll your eyes, there’s plenty to suggest that this is one of fall’s signature styles. Especially in the months of September and October, when the temperature is cooling off but still sunny and summery, this is one of the more obvious (but highly practical) style moves you can pull off while in the early phases of the autumn season. You might ridicule the look, but if it’s good enough for Jonah Hill, it’s good enough for us.

For the shorts, we’d recommend a pair of sport-focused shorts. While we’d lean toward an inseam somewhere between five and seven inches, we prefer bottoms with a technical bent, usually engineered in a waterproof or water-resistant mesh or nylon material (as opposed to options in a run-of-the-mill cotton). That said, some of our favorite brands have created a variety of sweatshorts which can also do the trick.

The hoodie is going to be the focal point of this style, so we’d suggest something more graphic that what you might be used to. That said, if oversized logos or over-the-top graphics aren’t something you’re willing to take on, fear not: A pop of color can work as a suitable, but less obvious, statement. With fewer pieces in the look, your footwear is just as important. While most sneakers should fit the bill, we lean toward trying a pair of high top sneakers (vintage Jordans are an easy choice, for example) worn with rolled-down crew socks. That’s just a starting thought, the important thing is that it coordinates (or strategically clashes) with what you’re working with up top.

Key Brands:
RRL, Visvim, Engineered Garments, Kapital, Levi’s, Carhartt, Dickies, Schott, Ben Davis

Key Pieces:
Straight Leg Selvedge Denim, Denim Trucker Jacket, Leather Biker Jacket, Chore Coat Army Surplus Cargo Pants, Workwear Trousers, Field Boots

How to Wear This Look:
The main issue with “Americana” is its sheer ubiquity. A combination of workwear and military fashion, the aesthetic is as much a testament to the United States’ global sartorial reach as much as it is a collection of garments. Japan’s reinterpretation of Americana, pioneered by brands like Visvim and Kapital, has helped preserve the aesthetic’s visual style and key pieces. That said, clear staples include the oft-referenced icons of American style: Levi’s 501 jeans and Type 2 trucker jackets, Schott Perfecto leather jackets, Dickies 574 work pants, Carhartt T-shirts and L.L. Bean Duck Boots (just to name a few).

The benefit of this ubiquity is that you probably have several of these key pieces (or pieces designed to replicate them) already stashed in your closet. As such, there’s no finesse to pulling off this look outside of simply wearing the pieces together. While we can give some rough outlines—avoid double denim, aim for a single turned-up cuff on your jeans, consider tucking-in your T-shirts—you’re probably already confident on how to make this workwear...well, work for you.

Key Brands:
Aimé Leon Dore, Noah, OAMC, Stussy, John Elliott, Supreme

Key Pieces:
Topcoat, Bomber Jacket, Luxury Hoodie, (Understated) Graphic T-Shirt, (Minimal), Casual Trousers, Designer Sneakers

How to Wear This Look:
It can be hard to realize, given the brand’s runaway success and global dominance, but streetwear isn’t just Supreme. As streetwear becomes ever-more intertwined with modern style across the spectrum, it makes sense that guys would want to incorporate the casual comfort of streetwear—without sacrificing their maturity. Fortunately, brands like Noah, Off-White and OAMC, run by streetwear design icons Brenden Babenzien, Virgil Abloh and Luke Meier respectively, clearly incorporate the hallmarks of street-inspired fashion into their conceptual (and in the case of the latter two, runway) collections.

In terms of what to look for, you’ll find two veins of product: upscale streetwear staples like hoodies and T-shirts, and tailoring produced by streetwear brands through their lens. For the former, look for hoodies with luxury production lineages (Canada, Portugal or Italy, for example) or graphic T-shirts with small or understated logos and designs. It’s less about ostentation and more about keeping things casual—but upscale. For the latter, a blend of street-inspired runway labels and stalwarts alike generally leverage their status to create tailored looked. For some that means atelier-designed tailoring, for others—like Supreme and Noah—Loro Piana or wide-wale corduroy blazers (respectively).

Sneakers, a streetwear centerpiece all their own, should tend to go for a more simplified approach in this category. While it’s perfectly permissible to wear pared-down (see: tonal or monochromatic) options from sportswear giants like Nike, adidas or Jordan Brand, there’s plenty of alternatives that should add a touch of luxe to your fit, without sacrificing its streetsmarts. If all else fails, opt for one of several flips on the Stan Smith (Common Projects is a great place to start)—the signature tennis shoe never goes out of style.

Key Brands:

Arc’teryx, Nike ACG, Patagonia, Timberland, The North Face, Nanamica, Danner, South2 West8

Key Pieces:
Cap or Bucket Hat, Waterproof Outer Shell, Fleece Jacket, Down Inner Layer, Tactical Vest, Olive of Camo Print Cargo Pants, Hiking Boots

How to Wear This Look:
Autumn’s chill means changing leaves and more time outdoors. The change of the season doesn’t mean sacrificing your personal style. Like streetwear, multiple brands—many available in national chains and boutique stores alike—have tapped into technical materials and techniques to fuse form with function. Whether you’re hiking off-piste or simply strolling the sidewalk, there’s nothing wrong with wanting your wardrobe to be as practical as it is stylish.

The key to this look is all in the layers. As the weather progresses into the inevitable winter, you’ll slide from lighter waterproof shells into packable down vests, to deep pile fleeces (layering under and over as you go). Brands like Arc’teryx produce superior raingear, Nike ACG and Patagonia provide practical (and colorful) fleeces and few can top The North Face’s climbing adjacent down outerwear. Fortunately, with their national (and in some cases, international) reach, mixing and matching these brands should be fairly simple. Besides, they generally all produce the same layering items, so purchasing one is as easy as determining which brand’s iteration you prefer.

As far as footwear, fall is the season for boots. That said, don’t simply opt for the same pair of auburn field boots that every basic bro has been buying since 2012. While there’s a variety of brands that fit the bill, opt for selections like Danner’s Mountain Light boot, or the classic L.L. Bean “Bean Boot” for time-tested outdoor classics. If nothing else, the six-inch Timberland boot isn’t just an obvious choice—it’s an outdoorsy icon in its own right.

Key Brands:
A.P.C., Acne Studios, Ami, Common Projects, Lemaire, Maison Margiela, Our Legacy

Key Pieces:
Wool Topcoat, Neutral Crewneck Sweater, Minimal or Unbranded Hoodie, Minimal Leather Jacket, Unbranded Indigo Chore Coat (or Denim Jacket), Light Wash Slim Jeans, Monochromatic Trainers

How to Wear This Look:
Sure, minimalism isn’t necessarily a look bound by the confines of a particular season, but it’s that flexibility that makes it a perfect choice for fall. As the name implies, building a minimalist wardrobe is predicated primarily on buying a number of pieces that, thanks to their simplicity, will be pieces you reach for all year round—not just fall after fall. With this in mind, consider each piece as an investment—there might be a larger upfront cost for each of the respective pieces you pick up under this style, but the “cost-per-wear” (as well as the sustainability “buy less-buy better” approach) makes this approach one of the most cost-effective in the long term.

Like the clothing, don’t overthink when it comes to the styling. Buying a sensible shade of blue denim (ideally with selvedge hems) to pair with neutral gray knits, unbranded T-shirts and monochromatic trainers—should be fairly simple to execute successfully. As autumn begins to tilt towards colder temperatures, a wool topcoat in a neutral tan, gray or subtle plaid check—combined with a pair of sleek chelsea boots—should accentuate (but not distract) from the minimalist style you’ve been perfecting earlier in the season.

Remember: It’s not that you’re blending into the background, you’re standing out by showing restraint. Given the ubiquity of highly-branded streetwear in modern menswear, this move to simplicity will be more impactful to onlookers than it might seem at first glance.