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What to wear when this winter has been unusually cold? I recently got back from a trip to Vancouver, and while the weather wasn’t that much cooler than evenings in San Francisco, my family and I took a trip up to Whistler – one of the local ski resort towns. Here in the Bay, I can usually get by with a thick cashmere sweater, tweed sport coat, and some kind of outerwear (although this year, I’ve been pining for some heavier dress coats given the falling temps). In Whistler, things were downright freezing.

There ought to be a saying about how 90% of your body heat escapes from your neck, because a chunky turtleneck sweater is one of the warmest things you can own. So warm that you may find yourself uncomfortable indoors, depending on the heating. I wore the one above from Asprey, which is no longer available, but you can find similar pieces this season from Scott & Charters, Inis Meain, Orvis, Thomas Maier, and Montgomery.

Thick turtlenecks are often too warm to layer over anything but t-shirts, but I like baselayers for my legs. I find tailored trousers don’t wear that much warmer than mid-weight denim, and I prefer the latter when the weather is particularly nasty (if only because I don’t have to fuss over jeans). Smartwool’s 250 baselayers are nice. Being made from pure merino wool, they’re more delicate than wool blends and synthetics, but also more insulating. 

Winter clothes for me is all about the materials. The soft hand of woolen flannel; the sturdiness of tweed. Waxed cotton can be a good way of keeping rain off your back, although bonded cotton can sometimes drape in more interesting ways. A plush alpaca blend sweater can also be a good alternative to cashmere, even if it sheds a little. The trick is finding something thick enough.

For the last year or so, I’ve been wanting to get a shearling jacket. Shearling being a kind of sheepskin, particularly from lamb, that has been cured so that the fleece remains attached to the leather (when the hide is taken from merino sheep, you have mouton).

Granted, shearling hasn’t had the best history. Not too long ago, the mere mention of it evoked ideas of the Marlboro Man. Those long, bulky, no-nonsense coats with patchwork-like seams running up the back and tufts of wool peeking out from beneath the cuffs. The silhouettes were blocky and the leathers were often dry and cracked, leaving the wearer looking vaguely like King Kong. As ranch coats and bomber jackets, shearlings carry a sort of rugged, workwear sensibility.

There have been times, however, when shearling was considerably more luxurious – even if still questionable in taste. In the early 1930s, clothing catalogs used to advertise their shearling coats alongside suede leather jackets and horsehide outerwear, seemingly ignoring the Great Depression. The material then came back in the ‘60s and ‘70s with the Peacock Revolution. Swanky men wore shearling coats with chunky turtleneck sweaters and velvet bellbottoms, presumably to their eternal regret years later.

Fabrics are my favorite part of fall/ winter wardrobes. Heavy tweeds, corduroys, and flannels for tailored clothing. Then sturdy wools and leathers for casualwear, as well as spongy alpacas and Shetlands for knits. Everything just looks and feels so cozy. 

The same goes for ties. Although few men need more than a handful of ties nowadays – some striped rep silks, solid-colored grenadines, and basic knits – seasonal neckwear is a great way to add joy to a wardrobe. Alan Cornett put it well recently when he said: “some purchases flavor a wardrobe, though their proportions are small.” A well-chosen tie, pocket square, or scarf is a great way to give a nod to a certain season or occasion, “changing the tenor of an ensemble.” A wool tie can complement the cold-weather feel of a tweed jacket, or add an autumnal touch to a navy worsted suit. 

There are thousands of fall/ winter ties out there, but broadly speaking, you’re looking at five categories:

Ralph Lauren will always have a special place in my heart. It’s the one company I really admired growing up – more in terms of how it was appropriated by streetwear culture, rather than the preppy Americana crowd it was originally intended for. I also think few companies have been as consistent and as great for so long. There isn’t much from their archive that I don’t think looks good today (just slim up some of the ‘90s stuff, Ralph!). 

About ten years ago, the now defunct Japanese menswear magazine Free & Easy published a special issue on Ralph Lauren (I put up a few pages from it here). Most of the clothes featured are long gone, of course. They were made sometime between the 1970s and ‘90s, although styles like them can still be found on Ralph Lauren’s site. For obsessives, vintage pieces come with a bit of provenance, but since some have become collectors’ items, prices can sky rocket into the thousands. Assuming you can even find them in the first place. 

For anyone trying to build a menswear company, Christian Kimber should be a case study. He’s a young, 28 year-old designer, born and bred in the south of England, but now living as a transplant in Australia. Over the last three years, he’s built a small, globally distributed label – carried at boutiques such as Gentry, as well as major department stores such as Bloomingdales – and recently opened his own brick-and-mortar store in Melbourne (at a time when everyone says B&Ms are dead). 

Christian is proof positive that you can do a lot if you’re driven to create. He doesn’t have any formal training – no fashion degree or design internship. As he puts it, everything has been sort of like “running a food truck in order to build up to a restaurant.” Three years ago, he was working odd jobs here in there in London’s fashion industry, doing sales work for My Wardrobe and Selfridges, then a bit of marketing for E. Tautz. It was from being in and around Savile Row that he picked up his love for tailoring. 

“At some point, I wanted a pair of olive suede tassel loafers,” he said. “I couldn’t find what I wanted, so I decided to make my own.” Christian designed the prototype, put together a run at a factory, and quickly sold through his inventory online. Most people with that success would charge forward, but Christian took a step back to think more about what he wanted to do with his newfound brand. “I took about a year-and-a-half off to really think about what sort of company would reflect me.” 

I like clothes in the summer that make you feel like you’re at home. Loosely-cut linen shirts that feel like pajamas, softly-tailored sport coats that disappear from your mind, and unlined loafers that wear like bedroom slippers. With the right clothes, every cafe and office can vaguely feel like you’re still bumming around your living room. 

I recently picked up a new pair of unlined pennies – Edward Green’s Harrow, which I’ve been pining over for years. On the surface, they’re just an unlined loafer with a pie-crust apron, much like you’d find on the company’s Dovers. The design, however, is actually by Wildsmith, a famed bespoke shoemaking firm that lasted for seven generations before shutting down. The company used to travel with some of London’s best tailoring companies, offering what they called their “three s’s”: shoes, shirts, and suits. 

The style was originally a bespoke country-house shoe made for King George VI, younger brother to the Duke of Windsor, Edward VIII. As the story goes, they were made slightly big so that he could wear them indoors with shooting hose. At some point, Wildsmith shut down the bespoke side of their operation and sold ready-made shoes produced by Edward Green (and, at times, Crockett & Jones). That’s how the Wildsmith loafer became the Edward Green Harrow. 

I found this photo on a friend’s Twitter feed last year. It’s from 1985 and shows the old Holliday & Brown shop in London. For those unfamiliar, Holliday & Brown was a legendary English tie-maker back in the day, although they also made shirts and dressing gowns. Here, one of their customers is being fitted for an ancient madder gown, with a sales associate showing what the sleeves will look like once they’re shortened.

I’ve been wanting an ancient madder gown ever since. Soft and chalky, I imagine wearing one would feel like you’re wrapped in a thin suede. Unfortunately, it seems they’re are no longer available today – at least in the kind of dusty, muted prints you see above. 

Some years ago, scientists found that two of the three dyes used to make madder caused cancer in rats. Which meant, when printers dyed their silks and dumped the solutions out to disposal plants, they risked getting carcinogens into water supplies. They never found a way to filter out those chemicals, so the dyes were banned and replaced with synthetics. Today, only the third dye (indigo) remains in its original form.  

Summer is a good time for lighter-colored shoes, but they’re not always the easiest to wear. Outside of plain white sneakers – which are admittedly pretty useful, even if ubiquitous – colors that are lighter than mid-brown often stick out too much from your trousers. Most men want to wear things that draw the eye upwards, putting the focus on their shirt, tie, and jacket combination. Lighter-colored shoes, on the other hand, often draw the eye down. 

There are a lots of exceptions. Tan shoes can look great with a pale gray suit, if only because they’re darker than the trousers (the other combination, tan shoes with a navy suit, almost always looks terrible for the opposite reason). I also think they work well with low-contrast ensembles, such as these in this post, or when the shoes are balanced out with a lighter-colored jacket. 

There are also some shoes that are just iconic, such as white buckskins. Having started with students at Princeton in the 1950s, white bucks quickly spread throughout the Ivy League school system, becoming “the shoe” for the style-conscious. Usual combinations included tan chinos or grey flannels, with the dirtiness of the buckskin being a source of pride (much like a well-worn button-down collar). They’re less commonly seen today, but their association with traditional American style endures. 

End made another round of markdowns and added some new things to their sale section last night. There are some surprisingly good deals, especially when you consider that some of their prices are already lower than what you’d pay in the US (mostly thanks to them discounting for VAT). 

Among some of the more surprising finds, there are Inis Meain and SNS Herning sweaters starting at $115.  Inis Meain’s linen crewnecks, for example, are just $119 (well below the $400+ you’d pay in the US). I wear mine with leather jackets on weekends. There’s also a good selection of Barbour jackets starting at $105, raw denim jeans for $89, and Buttero sneakers for just $115. 

Some other things I like:

Nothing softens the look of a leather jacket like suede. A plush, napped leather can be a good way to tone down the utilitarian origins of a bomber jacket or cafe racer – making them friendlier versions of their rugged counterparts. Want to wear a leather A-2 without looking like you’ve just stepped off the set of Top Gun? Or a double rider without people mistaking you for a Hells Angel? Get them in suede. 

The material can be particularly nice in the warmer months since it absorbs light. That gives the jacket a softer, more sophisticated appearance on a bright day than some of your smoother, shinier leathers. Plus, much like suede shoes, you can use them to add texture. A suede jacket lends visual interest to a plainer t-shirt or henley, but it also won’t clash with a patterned shirt. In the colder seasons, you can team one with a speckled Donegal sweater or cabled Aran for a texture-on-texture look. 

I recently picked up this suede five-zip from Maison Margiela (on sale at the moment at SSENSE). The design has been with the company for over ten years now, making it one of the more enduring non-traditional styles. It has long, diagonal zips across the chest – giving it an edge – although it’s still easy enough to wear with slim jeans or wool trousers. Pictured above: my Margiela jacket with a Barena henley, pair of 3sixteen jeans, and some Saint Laurent sneakers (the quality of the sneakers is admittedly terrible, especially for the price. Readers would be better off with Common Projects Achilles mid-tops in white).