If you’ve reached your fifth decade, you know better than anyone that fads come and go with the tides. You also have a well-honed personal sense of style, refined by years of knowing what works—and, better yet, what doesn’t. You probably also know that being 40 (and above) means looking polished, wearing timeless clothes that fit, and projecting an image that reflects your exalted station in life.
But if you need a refresher course—or are simply looking to stock up your closet for the coming season—allow us to offer some help. Some heroic brands—a few of which you’ve likely never heard of—have only one mission: to help you consistently look your best, year after year after year. Here, we’ve rounded up them. When it comes to stocking (and restocking) your wardrobe, stick with these guys. You’ll never have to concern yourself with a fad again.
Regent Fitted Dress Shirt
$92; buy now at brooksbrothers.com
They’ve dressed presidents. They’ve dressed movie stars. They’ve also dressed your colleagues—on every rung of the career ladder. In short, if you’re not wearing Brooks Brothers dress shirts by now, you’re not doing it right. (Pro tip: keep an eye out for holiday weekend sales, where you can generally pick up standard-issue button-downs for half off.)
The Iconic Rugby Shirt
$98; buy now at ralphlauren.com
You name it (polos, cufflinks, gala-worthy tuxes, double-breasted camel-hued suede bombers), and Ralph Lauren has it. But if you want to experience the best of what they have to offer, look to the preppy roots that helped immortalize the brand on the pantheon of men’s style. And for that, let the classic rugby—a potent mix of tough-guy magnetism and polished academic charm—be your starting point.
Park Avenue Cap-Toe Oxford
$395; buy now at allenedmonds.com
If you’re looking for the best bang for your buck—and, frankly, there’s never a reason not to—look no further than Allen Edmonds footwear. For starters, every pair is handmade (from a 128-step process, no less) with indestructibility in mind. But, if something happens to go wrong, to any degree, for a nominal fee, the company will restore the shoes to like-new condition. Oh, and also, each and every pair are timeless lookers. In short: a pair of Allen Edmonds shoes will literally last you a lifetime.
Want les Essentiels
O’Hare Leather-Trimmed Tote
$250; buy now at mrporter.com
If you don’t have one yet, know this: the tote bag is the best bag a man can own. And Want les Essentiels, with their streamlined designs and dedication to superior materials, makes the best tote bags on the market—at a fraction of the price of their highfalutin competitors. Just throw your stuff in and go, and look great while doing so.
Jetsetter Stretch Italian Wool Suit
$750; buy now at bonobos.com
The online-only Bonobos specializes in clothing that, put simply, is automatically tailored. Once you pinpoint your size and fit, by heading into one of their 50-plus “guideshops” around the country (where stylists can help you figure out what works best on your body), you can start ordering suits and shirts at the click of a button—and will never have to embark on a trip to the tailor again. Bonus: all orders have free shipping.
Silver Dial Chronograph
$130; buy now at jomashop.com
We get it: kickstarting a timepiece collection, especially if you’re buying online, is a daunting proposition. A few poor-choice purchases, and you’re thousands of dollars in the hole. That’s where Seiko comes in. Of all the many watch brands on the planet, none can match the sheer range of Seiko. So, if you want to test-drive a timepiece that’s a little bit out of your purview—like, say, a chronograph with funky rose-gold hands, a topographical face, and oversized numerals—you can do so at a relatively low-risk cost. Then, when you’re ready to upgrade to a Rolex-grade version, you can check out the company’s Grand Seiko look book, where you’ll find top-notch watches (and four- or five-figure price tags to match).
Cora Leather Jacket
$498; buy now at allsaints.com
Fact: every guy needs a leather jacket in his closet. But, once you top 40, the bells and whistles of the biker look championed by artsy post-grads will cause you to veer into mid-life crisis territory. Instead, stick with something more reserved and understated, without sacrificing material quality. That’s where All Saints comes in.
Supima Cotton Crew Neck
$9.90; buy now at uniqlo.com
There’s nothing exciting about Uniqlo, and therein lies the appeal. Their wares, from plain tees to graphic button-downs, are standard-issue at its finest—at prices you can’t find anywhere else. To be sure, the clothing runs a little slim. But if you find that it fits your frame just fine, order away in bulk.
$154 (was $280); buy now at backcountry.com
The 671,760 men who live in Phoenix, Arizona, can move right along. The rest of you, however, should take heed: good outerwear is an essential part of your wardrobe.
Whether you’re looking for jackets that can weather an Everest ascent, or just something that will keep your wool suits safe from a light drizzle, Helly Hansen is sure to have what you’re looking for. And if you purchase during the off-season (i.e., right now), you can score prices up to half off.
The Tie Bar
Texture 3-Piece Style Box
$49.95; buy now at nordstrom.com
Now, we’re not suggesting you stock up on ties at The Tie Bar. For sumptuous, well-designed neckwear, there are plenty of alternatives. (Plus, your tie collection should be robust enough by 40.) You should beeline to The Tie Bar, though, for suit accessories: pocket squares, lapel pins, and, of course, tie bars. Remember: no suit is complete unless and until it’s full accessorized.
Jeans in Slim Fit with GapFlex
$69.95; buy now at gap.com
When it comes to a cornerstone pair of jeans, most guys swear by Levi’s. But we’re going to posit an alternative: The Gap. Whatever the fit or hue, you’ll be able to find it at The Gap. The clincher, though, is the “GapFlex” fabric, which allows for extra give throughout the jean. Sure, it’s is a cheesy term, but, at the end of the day, you’re getting a leaner look and a more comfortable fit—and, given the fact that The Gap offers B.O.G.O. deals, like, every two weeks, at an amazing deal, too.
Finsbur Floral Geo Print Cotton Shirt
$133; buy now at tedbaker.com
The modern fits and splashy patterns of Ted Baker are a shot of adrenaline for a flatlined wardrobe. But thanks to a reserved, debonair vibe, you won’t run the risk of coming off as if you’re trying too hard. Wade into their wares with a dotted-lined floral button-up, which gives off serious minimalist vibes. And when you’re ready to shirk the blue-shirts-and-chinos look for good, you can dive headlong into the rest of their catalogue.
Wool Cashmere Tailored Coat
$1,890; buy now at burberry.com
Yes, Burberry coats are insanely expensive. They’re also the type of thing—timeless style, indestructible construction—you’ll have for your entire life. And if you think of clothing as investment, there are few better investments you can make than a good, warm coat. Think about it: From every day between late November and early April (give or take a few weeks, depending on your exact coordinates), you’ll reach for the thing. Wouldn’t you want the best, warmest, sturdiest number in your corner?
Waxwear Slim Brief
$398; buy now at katespade.com
Jack Spade may have officially closed shop a few years back, but you can still find their (best-in-show) bags around—in various department stores, and at sister brand Kate Spade, as a dedicated “gifts for him” line. Every bag from Jack Spade is a total stunner, from a design perspective, but we’re partial to the duffels and briefs made out of waxwear: a fabric that, when scuffed, retains the mark, so the bag develops a history-tinged rugged look as the years go by. The rarity is just another bonus cool factor.
Dolce & Gabbana
Light Blue Pour Homme
$116 for 6.7 oz.; buy now at bloomingdales.com
True style means that every part of you—even the parts most people won’t see—is 100 percent on point. Fragrance is no exception—and no one puts out better scents than Dolce & Gabbana. Case in point: Light Blue, which, as it name suggests, is a balanced, fresh cologne that runs zero risk of overpowering the room.
RB3025 58 Original
$178; buy now at sunglasshut.com
Face it: every guy harbors some degree of action-hero aspirations. Now, you can’t exactly roundhouse kick your way through town without repercussions, but you can dress like one. That’s where Ray-Ban, the pioneer of Tom Cruise’s favorite frames, comes in. There, you’ll find polarized (meaning: maximum UV protection) lenses of all shapes and sizes and colors. If, say, you don’t feel like rocking the mirrored grey or black lenses that are culturally well-worn by now, consider opting for a blue-spectrum gradient pair, like those pictured.
Red Wing Sheldon Boot
$369.99; buy now at clubmonaco.com
At Club Monaco, you name it, you can find it. But tucked amidst the waffle crew-neck sweaters and slim-cut wool trousers, you’ll find an impressive offering of third-party wares. Case in point: the company’s deep selection of Red Wing boots. We’re particular fond of the Sheldon, which features a clean-lined silhouette that works just as well with a suit as it does with distressed denim. If that particular flavor of debonair indestructibility is your cup of tea, beeline to your nearest Club Monaco.
Sensation Windowpane Check Trousers
$240; buy now at reiss.com
Reiss, a London-based clothier, offers smooth-tailored, Saville Row-inspired looks at a fraction of the price of what you’d find on the vaunted street. Exhibit A: these windowpane pants. If you look closely, you’ll notice they’re absent belt loops, which is a sign of utmost luxury (though you’ll probably have to take a quick trip to the tailor to get a perfect fit), and you’ll note that the patterning is faded just enough to keep the style on the proper side of stuffy banker digs.
Cotton Open Collar Polo
From $51; buy now at theory.com
Snobby fashionistas may sneer at Theory for copping runway looks but not quite attaining the runway pedigree. Thing is, therein lies the quality. With Theory, you absolutely can get runway looks without the runway pedigree—or price tag, either. Just look at this polo, which bucks trends (the open-neck collar, the non-tapered sleeves) left and right. It’s the future, for less.
Secret Wash Shirt in Heathered Poplin
$59.50; buy now at jcrew.com
Recently, J. Crew overhauled their entire brand. The mission: Make everything at the same high-quality benchmark, but at a fraction of the price. Thankfully, as this poplin button-down proves, the mission has been accomplished. (Shirts like this used to have an MSRP of about 25 percent higher before the overhaul.)
Petit Standard Slim-Fit Selvedge Jeans
$210; buy now at mrporter.com
Few delicacies on the planet can beat really good selvedge denim. It’s tough-as-nails, contours to your body, and—unlike normal, tear- and fade-prone denim—only gets better looking as the years go by. And if you’re looking for the best selvedge, look no further than the look books of A.P.C. Made from Japanese dry selvedge (that’s the ne plus ultra of the variety), it’s truly as good as it gets.
Ellis Chelsea Boot
$220; buy now at jackerwin.com
In essence, Jack Erwin is minimalism taken to maximum potential. You won’t find any groundbreaking trends here. Instead, you’ll find a curated selection of streamlined classics: cap-toe Oxfords, double-monk straps, penny loafers. Our favorite, though, is their Chelsea boot, which is cut slightly more narrow than similar boots, giving a more elegant, dashing look.
Slim-Fit Non-Iron Shirt
$54.99 each if you get 4; buy now at twillory.com
Every company on the planet makes a great dress shirt, these days. But, if you haven’t yet, consider checking out the well-cut options at Twillory. There, the more you buy, the more you save. The base price is $99 per shirt. If you buy in bulk (four or more), that drops down below $60. (Bonus: each shirt comes with a pair of nickel collar stays.)
Berlin Wingtip Brogues
$650; buy now at mrporter.com
It takes two months to make every pair of Church’s shoes, so you know you’re getting top-notch quality. When it comes to choosing your next pair of wingtips—the shoe that’s anchored men’s style for decades, and will for decades to come—spring for the best of the best.
Dragon Workwear Jacket
$268.80 (was $448); buy now at johnvarvatos.com
Fact: every guy wants to be a rock star. John Varvatos won’t make those dreams come true—but the clothes will help you look the part. You’ll find all the garden variety rocker gear, and then some. What truly sets John Varvatos apart from other rock-inspired brands is the courage to wade away from the studded leather jackets and beat-to-death skinny jeans to offer power-chord swagger in other forms, like this imposing embroidered jacket.
$125; buy now at bloomingdales.com
Yeah, yeah, we know what you’re thinking: dinosaur cufflinks?! When it comes to Paul Smith accessories, these barely scratch the surface of how zany things can get. The eye-popping tie bars and lapel pins are never overbearing, though. They just serve as easy ways to inject some fun into staid outfits.
Murray Cap Toe Boot
$210 (was $298); buy now at nordstrom.com
Come for the unique leather. Stay for the amazing designs. By now, Frye’s beat-up leather (which looks as if it’s tastefully survived a hundred winters) is ubiquitous. What shoppers might not know, though, is the company sells more than just biker boots. You’ll find Oxfords, backpacks, sneakers, messenger bags, and, yes, as pictured, even the occasional (hyper-stylish) dress boot.
Slim Fit Wash & Go Mélange Suit
$1,495; buy now at mrporter.com
Whether you’re shopping the sporty Z Zegna line or the upscale Ermenegildo Zegna collection, the company defies expectations at every turn. For proof, just look at this suit. Sure, it may look like a plain, if exceptionally well-cut, number. But get this: it’s machine-washable.
$12 (was $20); buy now at eddiebauer.com
No brand is more thoroughly equipped to help guys deal with the great outdoors—be it hiking, skiing, biking—than Eddie Bauer. Everything is rugged, cozy, and built to last. And, as you can with this hat (which is available in more than half a dozen colors, by the way), available in prices fit for buying in bulk.
Signature Leather Duffel
$299; buy now at llbean.com
While you may instantly recognize L.L. Bean for their iconic boots (which tend to sell out every year by early winter, so move fast), know that the company has much, much more to offer. Case in point: this handsome leather duffel, designed with both form and function in mind: At 44 liters of capacity, it’s practically bottomless—and looks terrific, too.
To Boot New York
Benjamin Leather Monk Strap Oxfords
$350; buy now at bloomingdales.com
We’re of the opinion that a guy can’t possibly have a deep enough stock of shoes. If you don’t yet have a pair of monk straps (a type of shoe that has all the class of a traditional lace-up, but twice the fun), now’s your time to start. The offerings from To Boot New York are quality, and a great way to wade into the trend.
Slim Leather Billfold
$195; buy now at nordstrom.com
Watches, bags, keychains, even bicycles—yes, Shinola is one of menswear’s greatest accessory makers. (Everything is hand-crafted right in Detroit, too, if all-American manufacturing is a thing you’re keen to support.) We’re over the moon for the company’s wallets, though, which make use of patented Horween leather, so your money can get carted around in something deserving of, well, your money.
$69.49; buy now at amazon.com
That’s right: men’s style is more than mere clothing—it’s about your grooming regimen, too. If you’ve yet to try Bevel, you’re sorely missing out. The company offers an entire suite of bespoke shaving products, but the real eye-catcher here is their signature super-powered razor. As one reviewer put it, “I just glide the blade on my skin and the hair disappears.” Oh, and a restock of blades is only about $10 for 20. Talk about a steal.
Cable Knit Sweater
$99; buy now at tommy.com
Tommy Hilfiger, the maestro of Americana chic, offers university-style preppy looks at bargain bin prices. But if you want to hew traditional—like, say, with a cozy navy cable knit sweater—you can find suitable options on that front, too.
$24; buy now at mackweldon.com
It’s the most essential layer of any guy’s outfit. If you’ve hit 40 and your underwear game isn’t yet on lock, it’s time to change that. And if you need a new base layer uniform, look to Mack Weldon. Their underwear is made with a proprietary moisture-wicking fabric, for maximum scent control, and are available in 26 different colors, so you can be as reserved or zany as your heart desires.
Tie 7 H en Folie
$180; buy now at hermes.com
Yes, $180 is steep for a tie. But, for when the occasion calls for it (job interviews, graduations, anniversaries, weddings), a guy should have a few of the most powerful power ties at his beck and call.
$175 (was $230); buy now at jackwills.com
Sure, Jack Wills tends to come across a little youthful. But, thanks to the whiff of English elegance that permeates their entire collection, you won’t look like you’re trying to pull off PacSun a few decades too late. Plus, as this modish peacoat shows, few brands nail the university vibe quite as well.
$89; buy now at amazon.com
Your clothes won’t mean anything if they get drenched. Enter: Davek, a company that make uber-stylish, idiot-proof umbrellas. They open and close at the push of a button, so you never have to fumble with awkward clasp systems in a busy foyer again. (We’re all guilty of that, right?)
Snapshot Card Case
$78; buy now at marcjacobs.com
If the idea of a cumbersome billfold gives you pause, just get a slim card case. But don’t be boring with it! Get creative—like with a vivaciously colored option. And when it comes to that, few brands can compete with Marc Jacobs, whose designers seem determined to make use of all 365 million colors visible to the human eye.
O’Connor Base Shawl-Collar Tuxedo
$4,980; buy now at neimanmarcus.com
Because 40 is well past the age where it’s okay to rent a tux.