Clothing can get expensive—like, really expensive. Need a new suit? That’s $500, easy, before tailoring is even factored. Shoes worn thin? That’s another couple bills, if you want a pair that’ll actually last. Tallying the costs is enough to cause a man to commit to a lifetime of pleated chinos and ill-fitted button-downs.
But before you retreat into a sartorial wasteland, know that things don’t have to be like this. In fact, you can pick up a veritable armada of stylish digs for the price of a single J. Crew overcoat. The key? Start with the basics. Scoop up a merino crewneck. Slip on a pair of sumptuous leather shoes. Rock a denim jacket (yes, they’re cool again). Herein, you’ll find all of those and more—and all at under a hundred bucks. Happy shopping.
Brooks Brothers Merino Wool Crewneck Sweater
$59.50; buy now at brooksbrothers.com
Every guy has one, and yet few men regularly opt to update theirs. Yes, the grey crewneck sweater is a fall and winter (and spring, depending on your climate) menswear essential. But, after a few seasons of consistent wear, the shoulders give out, and the waist stretches, transforming what would otherwise be a form-flattering merino sheathe into a slovenly sail of fabric. In other words: it’s probably time for an update.
Brooks Brothers Solid Oxford Polo Button-Down Shirt
$49.50; buy now at brooksbrothers.com
For easy layering, slide an OCBD (that’s menswear lingo for “Oxford collar button-down”) under a crewneck. A grey sweater over a light-pink shirt is a tried-and-true combo, but charcoal over white, burgundy over off-white, and any shade of blue over any other shade of blue also rank on the timeless-classic pantheon. Feel free to mix and match to your heart’s desire. Take heed, though: Since this OCBD is from the Red Fleece line, it’ll run a bit slimmer around the midsection than your standard Brooks Brothers button-down.
J. Crew Classic Denim Jacket
$98; buy now at jcrew.com
If you’re looking for an all-weather, all-season jacket, consider picking up a denim one. The days of the boxy, faux acid wash look are long gone. Instead, you’ll find streamlined silhouettes and rugged materials that ooze James Dean–level cool. And considering that jean jackets are tough as nails, your investment will last you until the next horrendous phase of ugly jackets rolls around.
Lacoste Classic Piqué Polo Shirt, L.12.12
$89.50; buy now at macys.com
Few closet staples are more versatile than the polo. It fits neatly into most dress-codes without sacrificing an ounce of cool. If the weather’s nice, no HR flack will send you home for wearing one; no bouncer will turn you away at the rope, either. Lacoste’s iconic iteration—which features bicep-hugging sleeves, a trim and fitted waist, refined color schemes, and feather-light cotton construction—gives you the best bang for your buck.
Levi’s 501 Original Fit Jeans
From $21.50 to $79.50; buy now at amazon.com
Is there a better pair of jeans than Levi’s 501? They fit like a glove, come in a vivid shade of indigo (don’t sit on a white sofa!), and are practically indestructible. Yes, it’s not for nothing this beautiful creation is considered a classic.
The Sperry Authentic Original A/O Boat Shoe
$95.00; buy now at macys.com
A loafer is too serious for casual settings. A slip-on sneaker is too casual for serious ones. Enter: The leather boat shoe, a genius innovation that effortlessly straddles the line between laid-back and buttoned-up. We recommend picking a pair up in light brown. It’s a less-harsh hue than black or navy, and will likely slide in seamlessly with whatever’s currently in your closet.
A|X Armani Exchange Basic Pima Crew
$29.50; buy now at amazon.com
Fellas, rejoice: Your lifelong Goldilocks-like quest for the perfect white t-shirt is over. Forget the Hanes or the Jockey. Instead, pick up this version from menswear’s godfather, Giorgio Armani himself. It’s not too baggy, not too slim. The sleeves show off just the right amount of bicep (if you have it) and the neckline shows off just a peek of pec (if you have that, too). And it’s made from a blend of pima cotton that’s just as soft as it is tough. This is one tee that’ll hold up wash after wash (after wash after wash).
MVMT Runway 60mm Polarized Aviator Sunglasses
$90.00; buy now at nordstrom.com
Get your Tom Cruise on and splurge on a pair of aviator-grade aviators. With burnished stainless frames and wholly polarized lenses (meaning: maximum UV protection), you’ll be safe to ride into any danger zone.
L.L.Bean Rangeley Flannel Shirt
$49.95; buy now at llbean.com
Beloved by denizens of both the Brooklyn Red Hook and the upstate one in equal measure (that is to say: hipsters and lumberjacks), L.L. Bean’s signature flannel has near-ubiquitous stylistic appeal. It’s also tough as nails, and certain to keep you warm no matter how low the mercury goes.
Converse Chuck Taylor All Star 70 Lace Up Sneakers
$80; buy now at bloomingdales.com
C’mon, guys. You can’t go wrong with the classic. You know it, you love it, it’s been around forever, and it’s certainly not going anywhere in the foreseeable future (even if you can peer into next century, we’d bet). There’s no better time to stock up than now.