They’re indestructible. They’re endlessly versatile. They’re form-flattering on anyone, of any gender, and have been since practically the dawn of recorded history. (Levi Strauss sold his first pair in San Francisco in 1853.) It’s no stretch to say that the Levi 501 ($98), the company’s signature fit, is the most timeless pant in history.
In 1917, Converse, then a humble footwear company in the Boston suburbs, introduced a basketball shoe to the American public. Five years later, at the behest of an American semi-pro basketball player who had some design ideas, the company tweaked the shoe into, well, pretty much what it is today ($55). That player’s name? Charles “Chuck” Taylor.
There’s a reason the camel topcoat has survived the fickle tastes of fashion: It works with everything and on everyone. (Indeed, as a color, camel might even be more versatile and match-friendly than white.) Back in the day, they used to be made from literal camel hair, hence the name. Originally designed in 1936 by Bausch & Lomb to help pilots protect their eyes and maintain their sight while flying (that’s where the name comes from) Aviators eventually became the signature model for Ray-Ban—and the go-to shades for a certain impossible-mission-tackling action star.
You more than likely have your fair share of t-shirts, ranging from ones sporting your favorite band’s last tour dates to ones that proudly display your pick of beer. But there’s something to be said for a timeless white t-shirt. Frankly, everyone should have at least one amazing white tee in their closet that can pair with everything from jeans to suits.
Tweed fabric has been around since the 1830s, when a London merchant apparently misread the word “tweel” on a label. It remained a popular material right up until Chanel made it a signature part of their fashion house. Elle explains, “There is nothing quite as iconic as a classic Chanel tweed piece. If you’ve had the honor of wearing one—a jacket, a dress, a skirt—you know that its texture, its weight, and its very aura are the things magic is made of.” Say what you will about the increasingly popular (and stylish) wearables trend: nothing beats a classic analog watch. Whether you’re blowing your bonus on a Rolex or saving up for a Patek Philippe, owning a nice watch isn’t just about owning a nice watch. It’s an investment in your future—and your kids’ future, and their kids’ future. You have an heirloom now. Hats have always been in vogue. And don’t take it from us—take it from the certified fashion rags! Glamour, for instance, collected 100 years of headwear for women while GQ put together 400 (!) years of hats for men. From the Cavalier seen in the British royal courts of the 1600s and cloche hats worn by women in the ’20s all the way down to the fascinators flaunted by today’s elite and the baseball caps seen on the streets, hat styles may be in constant flux. But there’s no doubt that hats as a whole have always been—and always will be—a staple for fashionable folks.
Pinstripes are always a stylish choice for those who want to capture a classically sophisticated vibe. But your fashion-sense doesn’t have to (and in fact shouldn’t) be inspired by a 1930s gangster or 1980s banker. Embrace modern sensibilities by sticking to a suit done up in the “chalk stripe” look ($799), which kind of looks a bit like a sun-faded tattoo.
The shearling coat has been an outerwear mainstay since at least the days of the Wild West. Back then, they were designed for maximum warmth during cold, dry winters. But nowadays, you’re more likely to see them in fall-ready denim or faux suede bombers—and there’s not an Instagram fashion feed on the planet these days that isn’t loaded up with the style. (Fair warning: while you may look amazing in a shearling coat, the most famous creature ever to wear a shearling coat will always, always be the Canadian IKEA monkey.) This wardrobe staple is something that many ladies like to keep in the closet in order to whip it out any time they need a reliable outfit for dates, dinners, clubs, and work events. While it sounds simple enough, everyone has a different version of the classic piece—one woman might prefer something a little shorter with no frills while another might like length and plenty of frills, for instance—which is why this is a trend that will never, ever go out of style. Today, high-heels may be associated with powerful women and even a dash of sex-appeal, but the origins of the style actually date all the way back to the 10th century. In fact, they were once designed for 15th-century Persian warriors to help the soldiers secure their feet in stirrups. By the early 17th century, upper-class women had adopted the style to make them more statuesque and they have remained a popular choice ever since for women (and some men) around the world.
In 1955, French couture designer Christian Dior introduced the world to the A-line skirt as a part of his spring collection. The style which is fitted at the waist and hips before getting increasingly wider towards the bottom can be worn in plenty of chic ways that can work as office wear, formal wear, and casual wear—basically, everyday wear. You may associate floral prints with spring skirts and summer shirts, but this timeless and endlessly varied pattern is practically as beloved as nature itself. Stunning on shirts, coats, boots, and even outfits for itty bitty babies, fashion-savvy dressers will always appreciate items adorned with flowers.
Rivaling floral prints for the adoration—and closet space—of nature-loving shoppers, animal prints may fade in and out of mainstream popularity, but they always manage to endure and resurge. Whether you’re into zebra print, cheetah print, cow print, snakeskin print, or tiger print (which is currently all the rage), you can stick with one style or mix them up for the ultimate animalistic aesthetic.
Riding boots aren’t just for those who are about to hop on a horse. While there are certainly styles that are better suited to actual equestrians, there are others that are made specifically for streetwear, even sporting a lowered heel that isn’t designed to hook nicely on an animal’s stirrup. From simple black riding boots to ones with elaborate flourishes and even loud options like this bright pink chrome-like pair, riding boots, in all their adaptability, will never go out of fashion.
Humphrey Bogart looked dapper in a trench coat in Casablanca in 1942. Audrey Hepburn made one a part of her iconic style in the 1961 film Breakfast at Tiffany’s. And in 1999, Keanu Reeves and company took the trench coat to new heights in The Matrix. Another classic style that gets an update every year (including last fall’s chicest choices), you can opt for a truly timeless option by investing in a classic Burberry trench that looks equally stylish on both men ($1,990) and women ($2,090).
There’s a reason the blazer has been around for centuries: Everyone looks better in one (when it’s properly tailored, at least). It tightens up the waist and broadens the shoulders, resulting in a trimmer, taller frame—and who doesn’t want that? Bonus: You never don’t look put-together and polished when wearing a blazer. The folks at Business Insider recognize that most of us “grew up thinking cashmere sweaters were the height of luxury.” Their coveted status was even immortalized during an episode of Seinfeld. And while this is an item that could set you back quite a bit, there are thankfully more affordable modern blends that will give you the look—and equally important: the feel—of cashmere.
Fabrics that come from animals may be culturally taboo these days, but thanks to high-quality faux versions, you can still enjoy leather jackets, fur-trimmed hoods, and suede shoes.
If there’s one garment that exists in every closet—among men and women, young and old—it’s the white button-up. Wear it dressed-to-the-nines. Wear it with jeans. Wear it with a pair of sweats. Wear it with nothing else! It always, always works. No other piece of clothing on the planet has the range. This one isn’t going anywhere.
C’mon: Pretty much from the second men started wearing them, suits have been a part of fashion. They’re not going anywhere. And if you think even the most old-timey iteration—the three-piece, complete with waistcoat and all—has already disappeared, think again. Given the sheer number of options on the market—from Armani to Zegna and pretty much every other designer on fashion’s rolodex—it’s more popular than ever. Just maybe don’t wear one on Casual Friday.
The double-breasted jacket has endured for one reason: It exudes gravitas. To make one work in today’s world, though, you probably want to avoid the railroad baron vibes. Dumb yours down a bit by pairing it with contrasting slacks and shirts in soft fabrics, like chambray.
While suspenders have certainly been more popular in the past—when they were an actual necessity—they’re experiencing a resurgence lately. Nowadays, people wear this centuries-old accessory more for style than practicality.
Audrey Hepburn was also well-known for her adoration of Breton tops, but she’s not the only one who championed the simple yet sophisticated stripes. The picture-perfect choice for country club members who like to spend a day at the pier or cruising around the lake on a yacht, Breton tops also regularly pop up on the runway in trend-setting seasonal lines that cater to anyone who enjoys a timeless preppy look. Safari adventures and hikes through the forest aren’t the only opportunities to slay some serious wilderness wear. If you’re into the outdoor vibe, then be sure to try out some fashion-approved options, whether that’s a killer pair of hiking boots or parka that could get you through an Antarctic trek unscathed. ae0fcc31ae342fd3a1346ebb1f342fcb You might think of the turtleneck as a dead style worn only by art curators from last century. You’d be wrong. Turtlenecks are just as strong today (at least among the fashion set) as they ever have been. Exhibit A: Ralph Lauren (age: 79), the king of American wardrobes—and always, no matter what, the most effortlessly best-dressed guy in the room—is still rocking the turtleneck. Once relegated to gyms and errands days, both Adidas and Nike have established themselves as powerhouses in the foot apparel industry, scoring famous faces like Lebron James and Kylie Jenner to promote their latest must-have sneakers.
No, it’s not just your grandpa who likes to wear loafers. For men and women both, the loafer is (and always has been) the footwear of choice for laid-back people who still care about their appearance—especially in the summer. For maximum style, go sock-free. And don’t stick a penny in it.
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