In an era when men can wear suits or sweatpants to work, it’s essential to know the foundational principles of looking good. Here are 20 timeless best practices from our favorite style experts and designers.
1. THE WORK BOOT WORKS WITH EVERYTHING.
A great pair of boots is an investment that will give your look character. And as they get worn in, they’ll become a part of your personal signature. You can wear a classic work boot everywhere and with everything from jeans at a concert to a suit on a date at a nice restaurant. Texas-based Helm Boots slims the profile of its made-in-the-USA stompers with the new Ayers model (pictured below). The slightly dressier silhouette still feels casual with a rubber sole and Helm’s trademark white stripe.
2. A SUIT IS MORE THAN A SUIT.
You probably don’t wear a suit to work every day, but it’s still an important wardrobe player if you pitch it right. The key is to pick a versatile style you can break apart and wear as separates. Look for a slim version with natural, unpadded shoulders and less-formal patch pockets, like Suitsupply’s Havana model ($499, us.suitsupply.com. The jacket can serve as a blazer with a pair of jeans, and the slim trousers will work with a casual sweater or even a high-low combination such as a hoodie and boots (see Rule 5). A solid shade is always a good choice, or dial it up with a subtle windowpane plaid in gray and camel Italian wool.
3. MAKE YOUR NEW PAIR OF JEANS 1990S-STYLE WASHED BLACK DENIM. No sweat if you missed Kurt Cobain, grunge and faded black denim the first time around. Somehow an amalgam of rocker bona fides and soulful nuance, washed and artfully distressed black jeans are the newest denim treatment for those bent on escaping the ever-present blues. Take Nudie Jeans’s interpretation from its Replica series based on actual worn pairs, in the skinny Grim Tim fit ($250, nudiejeans.com). To avoid flyover-country overtones, keep the look simple and sharp with just an inky black T-shirt or an urban parka and grounded with black lace-up boots or canvas kicks.
4. CLEAR IS THE NEW BLACK WHEN IT COMES TO EYEWEAR.
Going clear is a reverse-chic move that’s trending in both sunglasses and eyeglasses. Transparent frames signal that you’re above the style-wars fray, but their attitude makes an indelible impression nonetheless. Cutler and Gross offers splurge-a-rific see-through sunnies in either round or D-frame models with groovy green lenses, while Moscot’s squared-off 1960s Nebb style oozes The Graduate cool.
5. IT’S TIME TO ELEVATE YOUR HOODIE GAME.
No excuses. This fall, all the big designers have a heightened take on the humble hoodie: Rag & Bone’s black funnel-neck version under a slim overcoat, Michael Kors’s skiwear-inspired hoodie–bomber jacket hybrid or L.A. streetwear ace John Elliott’s oversize textured hoodie layered over his signature elongated tees. A spiffed-up hoodie, often in a fabric with a high-tech sheen, raises your style game without sacrificing the comfort of an old standby.
Women notice footwear. For that reason, the shoes are where any wardrobe overhaul should begin.
6. AND YES, THE SHOES WILL MAKE IT OR BREAK IT.
Women notice footwear. For that reason, among several others, the shoes are where any wardrobe overhaul should begin. The good news? Just as that pair of square-toed slip-ons you’ve had since high school will ruin your nine-to-five look, the right pair of suede loafers or pristine high-tops can raise an otherwise toned-down ensemble to new heights.
7. SPEND MONEY ON BIG ITEMS.
Certain things in your closet have a longer shelf life than others. Jeans, shirts and sweaters will wear out, look dated or get ruined by hot sauce within a few years. Outerwear, suits and leather-soled shoes can last decades. Three things to remember: First, buy in neutral tones such as navy, gray or black—colors that never go out of style. Second, learn how to spot-clean a jacket and use a shoe brush. Third, treat these items like the investments they are; if it doesn’t hurt a bit when you buy them, you’re not spending enough.
8. BUY QUALITY, NOT BRANDS.
It feels good to own a coveted label, but designer brands don’t always carry the same quality throughout their product range. If you’re going to splurge on a big name, make it count: Things like Burberry trenches, Gucci loafers and Brunello Cucinelli cashmere sweaters are iconic and worth the money. Yeezy white T-shirts, not so much.
9. YOU CAN CARRY A BACKPACK, BUT YOU NEED TO UP YOUR GAME.
There’s no reason to give up the hands-free convenience of a backpack out in the real world, but it’s time for a smarter-looking version. Emerging brand Haerfest (pronounced “harvest”) has just the ticket. Its J1 backpack (pictured below) is a luxury-meets-tech combo of leather and sturdy, line-patterned premium nylon. Neither too large nor too small, the carry-all features a fully lined main compartment and a front pouch, both cleanly designed with concealed zippers, as well as smaller interior zip pockets and an inner sleeve—all in a noticeable but still neutral olive.
10. WOULD-BE COLLECTORS, EMBRACE THE STARTER WATCH.
The classic Rolex Datejust tops the list for newcomers, according to Jon Goldfarb, owner of Second Time Around Watch Company, a Beverly Hills institution for 40 years. “It’s recognizable and holds its value. It’s something most people will recognize when a guy is wearing one on his wrist,” he says. The iconic watch dates back to 1945 and is still made today. Expect to shell out anywhere from the mid-$2,000s to the low $3,000s for a standard model; variables affecting the price include whether it’s all stainless or stainless with white or yellow gold, whether it has a classic silver dial or a more uncommon colored face, and whether it comes with its original presentation box and papers.
11. THIS IS THE ONLY SKIN PRODUCT YOU NEED TO FACE THE WORLD.
Hollywood men’s grooming expert Cheryl Marks, who tends to Will Arnett among other celebrities, says her guys go nuts over Jack Black Double Duty SPF 20 face moisturizer ($28, getjackblack.com). “It has everything they need, and they don’t feel like they have anything on,” she says. “It does its job and feels good on the skin.” Lightweight and non-oily, the potion hydrates skin for a better appearance and offers broad-spectrum protection against UVA and UVB rays. Fragrance-free and packed with vitamins and antioxidants, it’s formulated for all skin types.
The trend toward activewear does not give you carte blanche to rock your pajamas to dinner.
12. ATHLEISURE: JUST BECAUSE YOU CAN DOESN’T MEAN YOU SHOULD.
It’s now possible to be both comfortable and stylish (see: tapered sweats, ultralight runners, looser cuts), but there are limits. The trend toward activewear does not give you carte blanche to rock your pajamas to dinner or dress head-to-toe in matching logos like an off-duty gym teacher. The winning play here is moderation, combining one or two informal elements with an otherwise put-together look. Try a pair of monochromatic Nike Roshe Ones ($75, store.nike.com) with dark jeans for a style that’s equal parts sporty and polished.
13. BUY TRENDS IN ACCESSORIES.
Botanical prints are big right now. Buy them in shirts, socks, ties, maybe a five-panel hat—but not a suit. Trends are fun to wear, but they work best when combined with the classic standbys already in your wardrobe. Need proof? Google “Justin Timberlake denim suit.” You never want to be that guy.
14. SELVEDGE IS GOOD; STRETCH SELVEDGE IS BETTER.
Selvedge jeans in dark indigo are an integral part of any man’s wardrobe, but spending six months breaking in a pair is no fun. Recent advances in textile technology, however, have made it possible to have great-looking selvedge jeans that are also exceptionally comfortable from the first wear. Try on a pair of Naked & Famous Denim’s Weird Guy stretch selvedge ($166, tateandyoko.com) and you’ll never go back.
15. DON’T SETTLE FOR A SHIRT THAT DOESN’T FIT PROPERLY.
All shirts are not created equal, nor are they sized the same—so don’t settle for a button-down that doesn’t fit just right. Shorter, skinnier guys can turn to Uniqlo (sized for petite Japanese dudes) and Thom Browne, while classic American brands including J. Crew and Ralph Lauren tend to fall on the larger side. Once you find a shirt that suits you (shoulder seams should sit at the edge of your shoulders; the front should be snug without puckering), buy it in quantity.
16. YOU’LL NEED A TAILOR (A REALLY GOOD ONE).
Some guys can dress entirely off the rack and look great, but for the rest of us it takes a bit of modification. This is doubly true when it comes to suiting, which succeeds or fails depending on how well it fits your body. A good tailor can mean the difference between your looking like a kid in his dad’s suit and looking like the guy who owns the place. Do some research. Ask around. Approach the best-dressed man in your office and find out where he gets his clothes tailored. And then be explicit about what you want. Traditional tailors can be a conservative lot, so if you want that suit skinny, make sure they make it skinny. If you like a high-water look, don’t let them talk you out of it. The first time you wear a jacket or trousers that fit you perfectly, you’ll understand.
17. A LITTLE MILITARY GOES A LONG WAY.
Fashion has gone hard corps for fall, with military looks crowding the runways along with an attendant surfeit of shiny brass buttons, kitschy braid trim and tricked-out fatigue jackets. Serviceman style has been a perennial influence for designers, but you want to look current, not like you’re dressed for a costume party. Go for a contemporary interpretation such as the wool peacoat from John Varvatos (pictured above), with its regimental border stripe in a subtly contrasting gray and the unexpected but sleek addition of black leather panels at the pockets. As Mr. Varvatos himself says, “Military-inspired clothes are masculine and classic. They never go out of style, which is why men love wearing them each season.”
18. FIND A STYLE ICON AND LET HIM GUIDE YOU.
Maybe it’s your dad, maybe it’s Steve McQueen, maybe it’s Cornel West. These guys spent decades perfecting the art of dressing, and you could definitely learn a thing or two from them. Take note not just of what they wear, but of how they wear it, the countless details that make a studied outfit look effortless. Finally, make the look your own, adding and subtracting elements to tailor it to your lifestyle and personality.
19. BUY LOCAL (AND PAY A BIT MORE FOR IT).
Guys have more style options than ever before, from international mega-retailers as well as homegrown brands. Both have their strengths, but buying clothes that are made in the United States not only supports our economy, but the garments are often of much higher quality than fast-fashion imports. Check out Alden for shoes, Freeman for outerwear and Tanner Goods for belts and wallets. Spend a bit extra and feel good about wearing something made in your hometown.
20. ACCESSORIZE WISELY.
Personalize your style by working in a handcrafted accessory. It might be a rough-hammered silver bracelet, a worn and aged vintage belt or a handmade leather portfolio. Keep it simple and take some time to search out the talisman that says something about you.