4 Looks That Will Never Go Out Of Style
Gain a modern edge by investing in affordable, enduring pieces
Trends come and go, but style is timeless—and there are a few key pieces that will never go out of style. We narrowed it down to four no-fail looks that will keep you looking on-trend, even years after buying. Read on.
The Double-Breasted Suit
The double-breasted suit hasn’t always had the greatest ambassadors—remember Letterman in his supersize version, or John Gotti on his perp walks?
So it’s no surprise the DB, as it’s called, quietly retreated in the early 21st century. But it never fully disappeared. Now it has reemerged as a go-to style for well-dressed men.
Chief among the updates: a shorter jacket and a slimmer cut that shows off your body.
(Still need help? Here’s how to look damn good in a suit, every time.)
“These styles are more versatile,” says Patrick Johnson of the custom suitmaker P. Johnson Tailors. “Pair yours with a white twill shirt, a knit tie, and driving shoes or with a turtle or crewneck knit and canvas shoes.”
But don’t get carried away with patterns, he says. A solid or a subtle glen check or stripe works best.
Polo Ralph Lauren suit, $1,295
Suitsupply sweater, $149, and pocket square, $49
The Gray Flannel Suit
The actor Gregory Peck immortalized the gray flannel suit on film. But Gianni Agnelli, known as much for running the car company Fiat as for his impeccable taste in clothes, knocked the formality out of this classic by wearing it with driving loafers or lace-up tan suede boots.
“He made flannel look soft and sporty,” Johnson says. Another reason it has survived the generations: Flannel is forgiving. “The weight eats up any sort of imperfection, and it also drapes well, so it looks great on any body type,” he says.
Just make sure you avoid heavier British flannels in favor of lighter-weight Italian versions. Wear your suit with a knit polo, a superfine wool cardigan, or a patterned button-down shirt.
Related: How to Look Better in a Suit From Head to Toe
Suitsupply suit, $499
Eton shirt, $285
Military-Inspired Clothing
Modern camouflage can trace its roots to WWI, when technological advances turned brightly colored uniforms into deadly targets. Today, ironically, civilians turn to camo to stand out.
Military-inspired clothing, such as field jackets and stout leather boots, aren’t just fleeting trends but permanent fashion staples, says Christopher Serluco of the Fashion Institute of Technology. They’re as edgy with T-shirts and jeans as they are with sophisticated options.
The trick: “Treat camouflage and other military colors, such as olive and navy, like neutrals,” says Serluco. “They go with anything.” Stay modern by creating unexpected contrasts—like pairing a field jacket with a suit or wearing tailored sweatpants rendered in brushstroke camo.
(Military looks great for fall. Check out some more of our favorite transitional pieces for this season.)
Armani Exchange cardigan, $200
Vince shirt, $65
Guess joggers, $98
Cartography necklace, $199, and bracelet, $99
TAG Heuer Monza chronograph, $5,200
Heritage Pieces
From sturdy boots to denim shirts and jackets, work-wear is back. One of the biggest trends in menswear involves well-made, functional clothing that can take a beating and still look great.
“The denim jacket has definitely made the leap from mining to rock ‘n’ roll and catwalks,” says Jonathan Cheung, head of global design at Levi’s. The company first produced a tough, riveted jacket in the 1870s, and its chambray shirts debuted in 1913.
The key to keeping heritage feeling modern is choosing the right fit and fabric, says Cheung. The denim jacket you rocked when you still wore braces would now look worse than your overbite, so go for a more tailored look. Since new fabrics stretch, breathe, and repel moisture, you could even bike to work in them.
Related: 4 Clothing Items You Should Really Buy Used
7 for All Mankind jacket, $299
Levi’s Made & Crafted shirt, $218
Mavi pants, $98
Will Leather Goods belt, $185
Cartography bracelet, $199
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