Even if they’re both into style, the online communities for men’s clothing and fine horology exist on different islands. Guys who are into suits and Japanese workwear are often not that up on watches. And guys who are into watches are not always interested in clothes. These communities speak different languages, and have different standards for what makes something good. 

If you’re on this side of the divide – the one that’s more interested in menswear than mechanical movements – finding the right watch can be a challenge. For one, prices are dizzying. While you can get partially canvassed suits nowadays for $500, and full-grain leather shoes for half that amount, the ticket price for an entry-level, quality watch usually starts in the low four-figures – collector’s pieces are five-figures. That can make experimentation prohibitively expensive. Secondly, if you’re concerned about how to find a watch that actually complements the rest of your wardrobe, you have to learn a new visual language. Which watches go with suits, which go with workwear, and which go with contemporary menswear? 

I recently chatted with Greg Lellouche, co-founder of No Man Walks Alone (a sponsor on this site, although this isn’t a sponsored post) about how to find the right watch for any given wardrobe. Greg has been an avid watch collector since the late 1990s, when he bought his first one, the Sinn 142 ST you see him wearing above. Since then, he’s collected everything from vintage Rolexes to Speedmasters to Reversos. When he worked on Wall Street, Greg’s coworkers used to turn to him for advice when they were looking to buy a new wristwatch with their annual bonus. 

Much of men’s style takes after British tailoring, when dress norms were set during a different time period and climate. This is why, when we imagine a fall wardrobe, we think of the kind of heavy tweeds and wool overcoats that used to be seen in periodicals such as Apparel Arts. And yet, today, the cold season has been noticeably pushed back – late September still feels like summer and we’re months away from heavy outerwear weather. The biggest challenge for dressing this time of year is managing the wide temperature swings that can bring warm afternoons into chilly nights. Back when he was still writing about men’s style, Will Boehlke used to call this “shoulder season.”

It’s easy to dress well for early autumn if you rely on suits and sport coats. Instead of lightweight Frescos and linens, you want jackets in ribbed corduroys, mid-weight tweeds (nothing too heavy), and worsted wools. Worsted is just another way of saying the wool fibers were combed before they were spun into yarn, which makes the resulting fabric a little smoother and clearer finished (as opposed to woolens, which are left uncombed and are consequently spongier). 

There’s also a class of fabrics colloquially referred to as faux or citified tweeds. These are smooth, tightly woven worsteds made in rustic patterns reminiscent of traditional checks. They carry the distinctive colors and patterns of Scottish estates, as well as the tonal range best associated with the British countryside – bark, moss, and heather. They wear warmer than true summer fabrics, but don’t trap as much heat as real tweeds. Which is to say that they fit exactly in the middle. A couple of faux tweeds, along with a heavier navy sport coat in hopsack, serge, or this Sportex, and you’d have your early-fall tailored wardrobe covered. 

If prep ever makes a comeback, it’ll be because of lookbooks like Drake’s. For this coming fall/ winter season, they shot their collection of brushed Shetlands and tweedy outerwear against the collegiate Gothic architecture of Oxford University. The combination makes the photos look as though they were lifted straight out of Take Ivy. One of Drake’s employees, an Oxford alum who helped put this project together, led the team through his favorite parts of the campus and his old, familiar watering holes. 

Drake’s Creative Director, Michael Hill, doesn’t want you to think this is about Ivy Style, however. “We’ve always been inspired by Ivy clothing, but this isn’t about recreating a look,” he says. “It’s just that we’re close to Oxford and it’s a beautiful setting. Ivy is a style that inspires us greatly – we look back at provenance and history a lot. But this is also very much about doing something right for today, in our own way, and presenting our clothes in a manner that we feel was fun and playful.”

Playful is a good way to describe some of the new items this season. There’s a pocket square decorated with a spinning collage of space-floating astronauts (if you buy a truck-ton of those squares, I imagine they could make for cool wallpaper inside a nursery). I also like the single-stick London Undercover umbrellas that feature an archival print on the underside of the canopy, as well as the brightly colored, Kelim scarves (I bought the blue one). For the bold and fearless, there are block striped Shetlands coming soon. Those look as though Drake’s mashed together all the Shetland yarns they’ve run separately in the past and turned them into a single sweater. David Hockney, a man known for his eccentric embrace of color, would be proud. 

A couple of years ago, former Eidos designer Antonio Ciongoli and Stoffa founder Agyesh Madan headed to India to work on a collaboration. They developed two hand-dyed indigo fabrics – one shirting weight, the other trouser weight – and came up with a hand-block pattern for some prints. Unfortunately, the collaboration never came to fruition. Eidos’ parent company, Isaia, wasn’t sure how the market would react to unstable dyes (in contrast to synthetic dyes, natural dyes fade and run easily). Like Brooks Brothers’ customers in 1959, who angrily stormed back into the stores and complained about how their madras shirts were bleeding in the wash, they worried that people would mistake the character of natural dyes as defects. 

The work wasn’t all lost, however. Madan eventually used part of that trip for a Drake’s collaboration, and Ciongoli used it as inspiration for a new line. Since stepping down as Creative Director at Eidos – which is now run by Simon Spurr – Ciongoli has started 18 East, a new menswear apparel brand under Roller Rabbit. The line is debuting tonight at New York City’s 180 the Store. 

18 East isn’t necessarily a travel line, but it’s about traveling. The number 18 refers to how R is the 18th letter of the alphabet (a nod to their parent company, Roller Rabbit), and East is an allusion to Eastern manufacturing. “Everything we make is with small, artisanal suppliers,” Ciongoli explains. “When people talk about handwork, they’re often talking about how someone is operating a machine by hand. But handwork here means real handwork – even the embroideries are done purely by hand.” 

Hidden in the history of the tassel loafer is the story of why men’s dress has become increasingly casual with each passing generation. In the post-war period of the late-1940s, right when tweed jackets and Shetland sweaters dominated prep schools and Ivy League campuses, debonair actor Paul Lukas came back from Europe with a pair of oxfords. Their laces had little fringed tassels at the end, which Lukas thought made them look jauntier. So he took them to a couple of custom shoemakers to see if they could make something similar, and they in turn took the job to Alden. The company’s president at the time, Arthur Tarlow, came up with tassel loafers. That makes Alden’s model the original, and Paul Lukas the first man to wear this style. 

Alden’s tassel loafers were an instant success, but they didn’t exist in a vacuum. If you flip through any men’s clothing catalog from this period, you’ll see how much the idea of comfort had already supplanted Edwardian norms of propriety. Instead of high-button dress boots and gaiters, American clothiers were selling low-cut shoes such as white buckskins, brown oxfords, and canvas tennis shoes with rubber soles. In his 1982 Town & Country essay on loafers, which was later collected in his 1985 book Elegance, Bruce Boyer wrote: “To see these newer low-cut shoes side-by-side in the [1915] Brooks catalogue with the then more traditional higher-cut shoes is to realize immediately that back in 1915 the tide was unquestionably turning – had already turned in reality – and that men were allowing themselves more comfort in their dress. Heavy suits and boots, stiff collars, and high hats were all on the way out. Lightweight tweeds and flannels, button-down shirts and soft golf caps, Shetland sweaters and white bucks, had arrived.” The only thing missing from those 1915 catalogs were loafers, which were “the logical extension of comfortable and casual dress that marks the current century.” 

Tassel loafers were the norm by the 1960s, worn to business offices and government buildings alike, and favored by college graduates who wanted something dressier than their school-day pennies. But the tide turned again in the 1990s, when the style became a synecdoche for the country-club set and dishonest lawyers. In an all-too-often-cited New York Times article, Neil Lewis once reported that the term “tasseled loafer” was not just a way to describe a simple slip-on anymore, it was a political epithet:

Rummaging through a thrift store is not only a great way to score a deal, it can also be a way to find things you may not be able to get elsewhere – maybe a vintage tie made from hand block-printed silk, or a leather jacket that’s been perfectly beaten-up over the years. Unfortunately, thrifting takes time and effort, which means you have to love the process as much as the goods. These days, I’ll occasionally make it out to a flea market, but I rarely have time to actually dig through the dusty bins at Goodwill. 

I do my vintage shopping online, and often on Etsy. More than just a hub for DIY crafters, Etsy has become a marketplace for inveterate thrifters to showcase their finds to a wider audience (one of my favorite vintage shops, Wooden Sleepers, started on Etsy before opening up the brick-and-mortar you see above). I usually search for things such as French chore coats or the now-defunct Ralph Lauren Country label, but when you narrow in on a search term, you miss out on what could have otherwise been a serendipitous discovery – which is the real joy of vintage shopping. 

So, it helps to know some good stores. Here are twenty-one of what I think are the best for vintage Americana, workwear, and militaria, as well as a bit of Native American jewelry and home furnishings. Most stores these days only have a few good things buried underneath a heap of thrift store dregs, but these places have a higher hit ratio than most. I think they’re worth bookmarking. 

Men’s style in general, and tailored clothing in particular, can be very serious at times. Most of our clothes are inspired by hunting and war, and made in colors such as drab olive, stone gray, and stark white. Fashion historians trace this back to what they call The Great Masculine Renunciation, when men around the world – from the French court to Chinese nobles – traded in their colorful, sumptuous garb for the kind of austere, somber clothes British aristocrats favored. 

Rumisu, an accessories company based in Istanbul, is the antidote to this seriousness. They’re a young brand, having started in the summer of 2013, but they’ve already made big waves. They’ve been picked up by leading boutiques such as The Armoury, shown up on Ozwald Boatang’s runway, and received favorable write-ups in Monocle and L’Uomo Vogue. Much of that is because of how they’ve transformed luxury scarves and pocket squares – which are traditionally more conservative items – into playful, at times even goofy, accessories. Their designs invite you into a dreamed-up world of creativity, have a child-like wholesomeness, and are built around themes that are both inspiring and relatable. I find they’re a good reminder that, even when things aren’t going that well, it helps to have a sense of humor. 

The company is run by a trio: Deniz and Pinar, who are sisters, and Deniz’s husband Emir. Deniz and Pinar grew up together in Turkey, but have dramatically different backgrounds. Deniz studied fashion in NYC, and then returned home to Turkey to be a designer for an upscale clothing boutique, helping them produce their in-house line. Pinar, meanwhile, studied economics at Harvard and then earned an MBA at Wharton. Later in life, when she decided to do something more creative, she co-founded Rumisu with her sister and brother-in-law. “She’s become the total bohemian in the family,” Deniz says affectionately. “Early in our collections, we had a print titled ‘Come Out of Your Closet,’ which was inspired by Pinar coming out as a more artistic person when everyone expected something different from her.” 

The problem with buying nice things is never the cost of the items themselves, but the costs that can come after. Anthropologists call this the Diderot Effect, which is named after 18th century French philosopher Denis Diderot, who penned the essay “Regrets on Parting with My Old Dressing Gown.”

In it, Diderot rues throwing away his old gown after receiving a beautiful scarlet one from a friend. While initially delighted with the gift, his pleasure turned sour when he realized that nothing in his home properly reflected his new garment’s elegance. His tapestries were too shabby; his chairs creaky. So, one by one, he replaced his familiar, but well-worn furnishings with things that were fancier. He replaced his straw chairs with an armchair covered in fine Moroccan leather; his old desk with an expensive writing table; and his previously beloved prints with pricier paintings. 

In the end, Diderot found himself in debt and not even that comfortable in his new surroundings, as he realized his old possessions were just as good, if not better. “Why didn’t I keep my old dressing gown,” he lamented. “It molded all the folds of my body without inhibiting it; I was picturesque and handsome. The other one is stiff, and starchy, makes me look stodgy. There was no need to which its kindness didn’t loan itself, for indigence is almost always officious. If a book was covered in dust, one of its panels was there to wipe it off. If thickened ink refused to flow in my quill, it presented its flank. Traced in long black lines, one could see the services it had rendered me. These long lines announce the litterateur, the writer, the man who works. I now have the air of a rich good for nothing. No one knows who I am.”