For men who wish to dress better, the first cardinal rule anyone learns is to avoid black. Black suits are for morticians and Model United Nations representatives. Black shirts are for magicians and cruise ship DJs. Black shoes, at best, are for suits and eveningwear. In fact, giving up square-toed black shoes in favor of more anatomically correct brown ones became something of a rite of passage for well-dressed men twenty years ago. And in binning those shoes, many have learned to avoid black entirely. 

The thing to remember is that color has a rich and complex social meaning outside of traditional rules. Throughout the 19th and 20th centuries, black has come to signal arrogance and evil thanks to its association with anarchists, motorcycle rebels, and fascists. At the same time, it’s the color of humility and discretion. Think of how Quakers and Orthodox Jews have wrapped themselves in black in order to show their religious devotion. Additionally, writers and poets during The Beat Movement made black an intellectual color; designers such as Givenchy and Armani made it cool and cultivated. 

This nuanced appreciation of color is natural in womenswear, but it can take a while for more traditionally minded guys to think outside the box (or, at least, it did for me). Black footwear is de rigueur with navy and grey suits, and you wouldn’t want to wear anything else with a tuxedo. However, black can also be great for casual days. Black nicely complements colors such as navy and green, largely because of how those combos are associated with the military. With other black pieces, black can also look austere and chic. And in certain styles, such as Gucci’s horsebit loafer, black is simply iconic. 

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The explosion of sportswear and designer clothing after the Second World War shattered dress norms. Whereas men in the pre-war era were united by their allegiance to the coat and tie, fashion became a lot more diverse and divergent after the 1950s. Prole gear such as chambray shirts, five-pocket jeans, and white tees became popular off the worksite precisely because they represented something different – something more rebellious – to the more formal buttoned-down and strait-laced look of the establishment. Bruce Boyer has a nice essay about it in his book Rebel Style. 

To the degree there’s still a male uniform in the United States, it’s the dress shirt with dark jeans and a smooth merino knit. It’s the final outfit for men who don’t wear tailored jackets – the thing they can use to go to churches, offices, and other conservative settings without fear of drawing unwanted attention. It’s the thing your mother wanted you to wear when it came time to have your yearbook portrait taken. And likely what most men will be wearing next month at holiday parties.

The uniform persists for a reason. Shallow v-necks with dress collars underneath frame the face in a way that t-shirts can’t, and the combination gives a vague sense of formality without actually being formal. The look is nearly failsafe, but it’s also devoid of personality. A finely knit sweater in plain navy or gray is about as good of a candidate as any for a menswear staple, but I find I rarely wear mine. 

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If there was ever a reason to care about global warming – aside from total death of all living things on this planet – our ability to wear cool jackets should be it. As each year gets warmer and warmer, it feels like the opportunity to wear our favorite fall and winter clothes is getting shorter and shorter. It’s been unseasonably warm these past few months, but luckily the temperatures just dropped low enough to break out our favorite outerwear. And let’s be honest. Men’s style revolves around outerwear. 

Menswear blogs this time of year are often filled with lists about seasonal essentials – the perfect pea coat, the ideal trench. All of which can be great, but also feel a bit too generic to be personal. So while this isn’t a list of  menswear essentials, here’s a list of eight outerwear styles that have me excited this year. Hopefully you can find something here that also works for you. 

 

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I suppose one of the advantages of fall weather coming late is you get to take advantage of sales right when you actually want to wear heavy coats and knitwear. Today, Unionmade started their mid-season promotion. You can take 20% off almost anything with the checkout code FINALLYFALL. The only exclusions I see are Aldens, Il Bisonte, Birkenstock, and already marked-down items. 

The discount isn’t that deep, but it looks like the store has loosened their return policy. Mid-season sale purchases can now be returned, whereas Unionmade typically runs their end-of-season promotions on a final sale basis. That makes it a bit safer to take a chance on something. Some notable items I found:

• Levi’s Vintage Clothing: Levi’s Vintage Clothing recycles designs from the company’s expansive archive. I particularly like this hardy, loosely woven, red plaid shirt, which looks like it would layer well under rugged jackets. Their straight-legged 1947 501s are also great. The cut is slim, but forgiving, with a mid-rise that works with everything from sport coats to casualwear. 
  
• Kapital: This Japanese brand reworks folk clothing from around the world, producing things in odd fits and heavily patched up materials. I love their Ring Coat, for example, which is something like a love child between a Japanese kimono and an American army jacket. It’s oversized and enveloping, and will make you feel a bit cozier on a cold winter day. 
  
• Chimala: Subtler than Kapital, but more detailed than LVC, Chimala makes vintage-inspired workwear that looks like it’s been pulled out of the best thrift stores. Their chambray is one of my favorite casual button-ups. I also like this season’s canvas hunting coat, even if it’s clearly designed to only help you hunt for compliments. 
  

• Eidos: One of the easiest casualwear brands to wear. The designer behind the label, Antonio, is particularly good at making overcoats and knitwear, which can be paired with anything from jeans to tailored trousers. This season, they also have an indigo-dyed double rider, which was manufactured for them by leather jacket specialist Vanson. 
  
• Studio Nicholson: Maybe the most contemporary brand at Unionmade, this one veers towards minimalism and modernism, rather than workwear. Studio Nicholson is a celebrated womenswear brand that recently started making men’s clothing. I particularly like their oversized topcoats.  
• Knitwear, Knitwear, Knitwear: Finally, there are a ton of great sweaters on discount. See Howlin’ by Morrison’s Donegal crewnecks, Tomorrowland’s zig-zag alpacas, and John Sterner’s turtlenecks. The last one is a new brand by the man who founded Sutterheim. Some of the knits in there are insanely priced, but the simpler Lithuanian-made sweaters are more affordable. Well, at least with this mid-season promotion. 

For more discounts, you can check out Unionmade’s sale section. Just note those are final sale and the code doesn’t stack. 

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For being an iconic shoe, I’d be surprised if more than a hundred people have worn J.M. Weston’s Chasse. It’s one of the company’s flagship designs, but unlike their versatile 180 loafer, it’s a very particular. Chasse is French for hunt, so J.M. Weston’s Chasse is the company’s hunt derby. It’s a split-toe design with a short snout, bulky Norwegian welt, and triple-leather sole. It has a tank-like silhouette that wears you, rather than you wear it. Supposedly it was made for tromping out somewhere in the French countryside, presumably to hunt for compliments, although I’ve only seen them worn by shoe enthusiasts in Japan. 

Still, I’ve always liked the idea of a rustic split-toe, something more in keeping with the style’s workwear roots, rather than the sleek and sophisticated town models you see everywhere today. I’ve been working with Nicholas Templeman for the last year on a new bespoke commission that’s inspired by Chasse, but is toned down enough for San Francisco. The idea is to get a split-toe that sits perfectly between town and country – wearable in everyday environments, but also looks at home with tweed and denim. 

That’s meant getting certain details right. My last had to be adjusted to reflect a shorter and more rounded toe shape; a seam has been made going from the quarters to the facings. I’ve also opted for a bellow tongue, which means a bit of kidskin leather has been used to connect the tongue to the facings. This is typically done on country shoes to prevent rain or pig slop from seeping in. Or, in my case, used to justify to myself why I’m getting custom shoes. 

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Tailoring is often described in regional or house terms. Anderson & Sheppard’s iconic drape cut is soft shouldered and full throughout the chest, making even the most frail and pudgy look athletic. Conversely, Huntsman’s imposing shoulder line and flared skirt, which kicks out from the hips, accentuates their X-shaped silhouettes. Huntsman’s cut is derived from their heritage, obvious from the company’s name, back when the firm used to tailor for Europe’s hunting and riding aristocracy.  

Over the years, I’ve realized these generalizations only take you so far. In reality, there’s no such thing as an Anderson & Sheppard cut – only a specific cutter’s interpretation of a house style. The word cutter is a tailoring term for a person who drafts a pattern and cuts the cloth, sort of like the architect behind a building. Large tailoring houses can have two or three cutters, maybe more if you count the people making trousers, which means the same number of people can walk into a shop and come out with surprisingly different garments. If you like a bespoke suit or sport coat, it’s just as important to ask who was the cutter as it is to ask about the tailoring house. 

Which is why I like working with small tailoring shops, where the cutter’s name is on the door. You have a better chance of knowing who cut each of the garments that carries the shop’s label. One such cutter-run firm is Steven Hitchcock’s, who’s been in the tailoring business for over twenty-seven years. He left school at age sixteen to find a trade, first puttering around with the idea of becoming a mechanic (he even took some classes for it). “At some point, my grandfather suggested I spend a day with my dad, John Hitchcock, who at the time was a trouser cutter at Anderson & Sheppard,” says Steven. “It ended up being fantastic. I thoroughly enjoyed seeing a pair of trousers get cut and made, as well as celebrities such as Liam Neeson walk through those doors.”

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No Man Walks Alone is an advertiser on this site, but also one of my favorite stores. Greg, the company’s founder (who can be seen pictured above), simply has great taste in both tailored clothing and casualwear. Guys who are used to wearing suits during the workweek can find themselves at a loss on how to dress casually. Similarly, men who know how to dress casually can sometimes be confused on where to pick up a good suit. No Man Walks Alone is one of those rare stores that can serve both types of people. 

This weekend also marks their fourth year in business, so they’re celebrating with a five-day sale. Take 20% off anything with the checkout code FOURTH. Unlike No Man Walks Alone’s end-of-season sales, these mid-season promotions allow for returns, which makes it safer to take a chance on something. Here are ten things I think are particularly worth a closer look:

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No one in the fashion industry ever admits to being in the fashion industry. For all the designers and tailors I’ve spoken to over the years, I’ve found they all say the same thing – they’re not interested in fashion, they don’t follow trends, and they’re about making things that last. That’s true whether they’re hand tailoring three-piece suits or slapping together the cheapest possible black double rider. 

No brand, however, embodies the anti-fashion ethos more than S.E.H. Kelly, a micro-sized brand run by just two people – Sara E. H. Kelly, after which the company is named, and her partner Paul Vincent. Their collections are small, albeit growing, with just a few designs and some basics to accompany them. There are some mid-weight, medium-wale corduroy shirts, including some pullovers with unusual collars, as well as subtly pleated trousers with buckle-back and side-tab details. The stars of the collection tend to be in outerwear, where you’ll find trench coats made from stealth-quality Ventile cotton, as well as raglan-sleeved Balmacaans constructed from the loveliest Donegal tweeds. 

Their collection mostly stays the same from year to year, with a new design dropping once in a blue moon. "When Sara and I started the company, we wanted to do this on an ‘as-and-when’ basis,” says Paul. “Meaning, as we develop new patterns and when we find interesting cloths. Five years ago, we only had three jackets, and the following year, we didn’t have anything new, so we reintroduced the old designs in new fabrics. Now the collection is growing, so we occasionally rotate things in and out, but we still mostly make things with slight updates.”

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Back in the early 1940s, Leon Leonwood Bean – founder of L.L. Bean – wrote a practical guide on living in the great outdoors. The point of the book, he wrote, is not to “bore readers with personal yarns and experiences, but to give definite information in the fewest words possible on how to hunt, fish, and camp.” The book, while not that well edited, is tightly packaged into 104 pages. It also covers everything from building beds to cooking outdoors to finding lost hunters. You can find it these days through Amazon (it makes for a nice gift for outdoor enthusiasts), although it’s also available for a free read through Google Books. 

Naturally, for the purposes of this blog, the most interesting section is chapter twelve, which covers what to wear when you’re out in the hills. Leon Bean suggests taking along a pair of 12″ leather top rubbers (what I assume are his Bean boots) and shorter 6.5″ moccasins for dry days, when you’re out on the ridge before it starts snowing. Pants should be medium-weight wools built with knitted or zippered bottoms; outerwear ought to include a medium-weight, all wool coat with a game pocket at the back; shirts should likewise be made from wool, with at least one being a red paid in case “you go out to drag a deer without a coat” (that way, you won’t be shot by other hunters.) A sign of his times, Bean suggests leaving the house with your heaviest business suit. And for handkerchiefs, he says to take along six red bandanas (never anything white). “I also recommend colored toilet paper,” he writes. 

The excerpt is charming, and even if it’s a bit antiquated, it nicely describes a sort of autumn style that still feels relevant today. To be sure, outdoor clothing has always defined fall wardrobes, whether that’s tweed sport coats worn out in English countrysides or the sort of workwear Bean favored. For me, a big inspiration at the moment is Japanese hiking gear – a little more casual than traditional tailoring, a touch less rugged than shooting apparel. No less outdoorsy. 

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It’s easy to fall in love with a pair of oxfords, particularly if you’re browsing for shoes online. They’re naturally sleek, with minimally detailed uppers that give the shoes a sense of formality. And for many people, dressing up is the same as dressing well. Derbies by comparison can get lost in the mix, but I find them infinitely more practical. Like most men, I rarely wear suits. And for daily use, oxfords just look off to me with sport coats and trousers – even worse with jeans. They’re simply too formal. 

When it comes to derbies, none make my heart pitter patter as much as the Norwegian split toe. I love them for both their design and how much they repulse others. It’s true they can look a bit taxidermic. And if done poorly, an elongated toe seam can even seem phallic. When everything comes together well, however, nothing looks as good to me. Wingtips are too common; cap toes too plain. Norwegian split toes plant your feet in the ground and say you like something a little different. 

Apparently, the style has some workwear roots. John Lobb of St. James calls the style a Navvy cut for how they used to be worn by British navigational engineers (or navvies for short). Nicholas Templeman, who used to work as a lastmaker at the company, tells me men used to wear them when they worked on canals, railways, and roads:

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