The first thing you put on each day should instantly boost your confidence. It should also be comfier than all get-out. Don’t cheap out here. Quality basics are worth a few extra bucks, but you should expect to turn over your daily rotation every six months. As always, we'll spotlight Supreme's consistent collab with Hanes, but—whether it's classic Calvin Klein or a smaller undergarment specific brand—we recognize it's a highly personal choice.

Nothing beats a crisp white T-shirt. While Supreme provides its own flip on the classic Hanes three-pack, you can also switch it up with Uniqlo's equally top-notch plain white tees (featuring proprietary Airism or Heattech technology). Just make sure the fit is spot-on. That way you can wear it standalone, or layered up under all the flannels, sweatshirts, jackets and jerseys that fill out your closet.

Maybe it’s straightforward Supreme. Maybe it’s a vintage band tee. Maybe it’s something different entirely. The only rule is this: Avoid imagery that will make you cringe three years from now.

No matter how deep you go down the rabbit hole of far-out washes and funky distressing, keep at least one pair of flexible jeans in your bottom drawer. From classic Levi’s 501 to selvedge Saint Laurent, there’s high-quality denim at every price point. A.P.C.’s is a great brand to start exploring if you’re looking to expand beyond the Levi’s you can buy at the mall (without sacrificing your budget).

Corduroys or chinos, belt loops or side tabs, skinny-fit or wide-leg. The choices are endless. The important thing is that you’ve got an appealing alternative to denim on hand. Wool drawstring trousers—which can play casual or formal depending on how you wear them—are a fine place to start. Acne Studios is highly recommended for beginners here, with options that can embody minimalism, or go out-of-the-box with print and texture.

It’s not fall and winter forever, so we also recommend keeping casual shorts around, even if it’s just a basic pair of Patagonia Baggies. Odds are, you’ll end up wearing them more than you expect—especially once the dog days of summer roll around.

Oxford shirts have been a foundational menswear piece for more than a century. Which means most major designers have put their own spin on the design. Find one that jibes with your look, then buy two of them—one in white, the other blue. It’s fairly obvious, but it’s going to be the bedrock of your “work” (and post-work “play”) wardrobe.

Polos are the ideal “tweener”—perfect when a collarless shirt feels too casual, but tailoring would be overkill. For a timeless design that won’t break the bank, consider shopping the feed for Ralph Lauren (we have a classic style in mind), Lacoste or Fred Perry, three labels that helped make the polo shirt a staple.

Yes, you should have one in a neutral color. But neutral doesn’t mean boring. Subtle detailing, like Maison Margiela’s four exposed pick stitches (a signature for the minimalist-meets-conceptual brand), can elevate a standard black, gray or navy jumper. Meanwhile, a strict minimalist design (think: A.P.C. or The Row) will only emphasize your most interesting jackets and footwear.

Hoodies are the pinnacle of egalitarian fashion. We won’t knock you for dropping serious dough on your dream sweatshirt. But a clean blank from Champion gets the job done, too.

The easiest way to polish an outfit? An unstructured navy blazer. Start with a cotton or linen blend (unlined) for year-round wearability, then start adding wool or cashmere options for colder months. Given that this isn’t part of a complete suit (more on that later) you can opt for something that’s luxe, but more informal. Trust us, there’s a difference.

Various types of suiting—and the suit itself—cycle in and out of fashion. Two things that never change: Black and navy suits are tops for versatility, and the jacket needs to fit in the shoulders. Past that, a good tailor should be able to handle the rest. For something a bit more forward facing (without feeling hard to wear) consider tailoring the trousers up a little higher than what you’re used to (tell your tailor “no break” and he’ll know what to do).

Everybody needs oxfords (or at least loafers) for kicking around at formal events. Good news is that a well-made pair can last decades. Start with black or brown, and pick up a leather belt in the same color to match.

Smart white shoes are the bedrock of any sneaker collection. Yours might be chunky retros, understated canvas, Euro trainers, hoops-inspired, or patent leather luxe. Regardless, it’s probably best to keep them clean.

The safe play is sticking to the Three C’s (chukka, chelsea, combat), or a pair of hard-wearing work boots. That said, the right sneaker boots can also do the trick. Just have a weatherproof option (with Vibram soles if you’re lucky) on deck if there’s a chance of snow.

Think of a good raincoat as the insurance policy for protecting your T-shirt collection, favorite hoodies, and priciest knits. The traditional choice is a trench (Burberry and Mackintosh are perennial favorites), but other, more technical options abound.

Junya Watanabe and Hedi Slimane both riffed on the iconic Perfecto biker jacket to create modern icons of their own. Those are killer pieces, provided you’ve got deep pockets. Otherwise, look for an original from Schott, which sell for a fraction of the cost and pack plenty of moto-punk edge.

Conventional wisdom says you can’t wear a denim jacket with jeans. Truth is, you can wear a denim jacket with anything, provided the cut is impeccable and you’ve got the confidence to carry it. And, like your favorite jeans, this is one item that only gets better with age.

Duffle, teddy, military, puffer, double-breasted—take your pick. Remember that during the winter months you’ll be wearing a coat everyday. So coordinate with your other cold-weather clothing accordingly.

Hats are an accessory. As in, not required for daily wear. That makes them perfect for a lighthearted touch. Throw on a laid-back dad cap whenever the mood strikes—even if that’s only when you’re actually hanging with your dad.

The bolder among us have reclaimed small cross-body bags. For everybody else, there are backpacks and totes. Big on utility, sure, and equally cool in full-grain leather (for a professional vibe) as full-on graphic canvas (that New Yorker tote you've been seeing everywhere is just one example)

Besides your phone, a wallet is probably the accessory you reach for most on a daily basis. It’s also one of the simplest upgrades to make. Get one that’s worthy of holding the credit cards inside of it.

If you can put a Rolex or Patek on your wrist, go for it. But brands like Seiko and Hamilton offer fine watches at reasonable prices, while the G-Shock cult is strong these days. Don’t sleep on Timex, either—the company's recent collabs with Todd Snyder to Engineered Garments are seriously good.

To ensure they work with your face shape, you’ll need to try on sunglasses before buying them. Unless those sunglasses are Ray-Ban Wayfarers. Don’t complicate things: Make these your first pair of shades, and build from there.