These boots have been sitting in my closet for a while. I bought them a couple of years ago when I was getting into heavy horsehide jackets and flannel shirts. These days, when I’m not in sport coats, I’m usually wearing more contemporary takes on casualwear – or off-beat riffs on classics – but when it was raining heavily last week, I broke out my engineer boots again.

Much like the five-pocket jean and oxford shirt, the engineer boot is an American classic. A Heddels writer once described them as having the ruggedness of Pacific Northwest logging footwear, but the simplicity of English riding boots, which sounds about right. Engineer boots are defined by their tall, stove-pipe shaft and roller-buckle ankle strap (often accompanied by a similar strap around the calf). The style was originally worn by railmen – particularly those who shoveled hot coals into engines – because they offered protection from sharp shovels and fiery embers.

Like a lot of workwear, engineer boots became popular as everyday, casual garb around the 1950s, when more rugged styles were adopted by youths and returning veterans seeking to carve out new identities (ones that defined them as separate from the flannel-suit-wearing elites). Members of motorcycle clubs first started wearing them as part of their double-rider uniform, as the smooth design ensured that no shoestrings would get caught in their bikes. Later, Marlon Brando and James Dean helped spread this look through their various movie roles, which is what made them popular with youths. By the end of the decade, engineer boots carried a sort of bad-ass connotation that has stayed with them to this day.

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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. 

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It’s amazing how much of our wardrobe comes from the military. Every other person you see nowadays is dressed to kill. Men in cafes wearing Melton wool pea coats and heavy leather bombers; women in Army green field jackets; and businessmen with large, cotton gabardine trench coats thrown over their suits. Even seemingly innocuous items have their roots in war. Chinos, for example, were originally worn by British and French servicemen in the 19th century. Today, they’re just standard issue for cubicle farmers. 

One military style I’ve been into lately is the jeep coat – a short, double breasted design that American soldiers once wore during the Second World War. Some look like they’re little more than olive colored versions of naval pea coats, but I favor the more dramatic styles with shawl collars (see an example above). 

Since fashion is all about repurposing design, you have to go back to the turn of the 20th century to really understand jeep coats. Back then, fur traders and loggers in the Pacific Northwest would wear blanket coats – called so because they were made from the garishly patterned, brightly colored blankets. The coats were double breasted in order to keep the wearer warm, but also cut short to allow for easy movement. These were work clothes, after all, even if the style would later spread throughout the US – first as souvenir gifts, then as fashion items, and finally as military garb. 

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Gloves aren’t just a style statement this time of year; they’re a practical necessity if you live someplace cold. I’m in Canada at the moment, visiting family, and can’t even leave the house without a pair already on. Plus, check out Luciano Barbera’s beautifully aged gloves pictured above – old and richly patina’d from years of use. Such gracefully aged gloves can be a nice way to add interest to a winter ensemble. 

If you can only own one pair, get them in dark brown. Something made from a soft and supple Nappa leather will be versatile enough to go with almost anything. You’ll also want to get them wool-lined, if not at least cashmere-lined. Unlined gloves fit closer to the hand, but you’ll appreciate the added warmth of wool-lined gloves when temperatures drop below forty. 

If you have room for more than one pair, however, I think it’s nice to get some that go with certain outfits. Think about the material, stitching, lining, and even silhouette (yes, gloves have silhouettes). A rundown of what I find particularly useful for my wardrobe:

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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.

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End-of-season sales can be a great time to nab something nice, but there are so many good stores nowadays that it can feel overwhelming to sort through everyone’s inventory. Since there are dozens of winter sales going on right now, I thought I’d round up some of my favorites. Most notable are megastores such as Mr. Porter and End, both of which start their promotions today, but there are also tons of great deals at smaller boutiques. 

Mr. Porter: Mr. Porter is always the highlight of every sale season. Discounts tend to start around 30% to 50% off, and then go deeper over the next few weeks. The problem is that things tend to move fast, and very little is left after a few days. On the upside, the selection is amazing. 

To get through the inventory quickly, make use of the site’s navigation filters, where you can hone-in on things by brand and size. If you need suggestions, I think Nigel Cabourn, Engineered Garments, and Chimala are particularly good for workwear; Eidos and Margaret Howell for contemporary casualwear (those Howell duffle coats and fishtail parkas look amazing); and William Lockie for cashmere knits. 

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There are a lot of things I love about living in the Bay Area – the food and bar scene, the relatively diverse community, and the summer/ fall festivals. The only thing I hate is the real estate. Housing is expensive, gentrification is rampant, and for the kind of buildings I like to live in, home insulation isn’t that great. Unless you’re in a new building or can afford some multi-million dollar house, old buildings, especially Craftsman ones, are kind of drafty. 

I used to waste a lot a money in the winter on heating bills, but a couple of years ago, found that I could cut that back with some good cashmere sweaters. Cashmere knits may be the only things that can be rightly called investment pieces. They’re expensive, but depending on where you live, you’ll make up the cost in what you’ll save on heating. 

In some early-20th century trade journals, you’ll find rumors that the finest cashmere used to come from Russia, but for at least the last hundred years, China and Central Asia have been the main sources. From the mountains up Tibet and away across the back of the Himalayas to Bokhara, cashmere travels much like the way it did before Marco Polo explored the Great Silk Roads. It comes down from the mountains in countless little loads on the backs of yaks and horses – sometimes buoyed down interminable waterways on rafts and boats – before reaching a major hub, where it’s put on modern transport and swiftly whisked away to Europe. If you’re wondering why cashmere should have to travel so far across Asia, just remember the stories of the still unconquered Everest. Across the vast barrier of the Himalayas, there are few routes. 

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This might be one of the best Brooks Brothers sales I’ve seen in years. First, select items have been discounted between 25% and 40%, which on face value isn’t that unusual. Except until the end of Saturday, you can knock another 25% off with the checkout code DECBC16. That brings the total discount as low as 55% off retail.

The discounts get even lower if you pay with a gift card. At the moment, they’re offering a free $25 eGift card for every $150 eGift card you purchase. To get the bonuses, you have to purchase each of the $150 eGift cards separately. The credits will be immediately emailed to you and you can apply them to any purchase, which makes all the discounts above stackable. 

Note: customers are limited to five $150 eGift card purchases, and apparently you can only apply three of the $175 eGift card credits to any one online order. But shipping is just $1, so you use all five in separate multi-item orders. 

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I love this photo of Glenn O’Brien strolling down some NYC street in a dressing gown and leather huaraches. Designers have been trying to turn pajamas into glamorous streetwear for the last two or three years, and while I agree with Robin Givhan that you should resist, wearing something like this in the morning while walking your dog just sounds fun. 

I bought my first dressing gown last year. It was a bespoke commission from Ascot Chang, with the gown itself made from a length of mid-weight, grey windowpane Fox flannel. It’s great for chilly winter mornings, but a little too heavy for spring and summer. So I’ve since picked up two more – one made from an indigo-dyed Khadi (a kind of handspun, handwoven Indian cotton fabric) and another in a dotted navy silk. 

One of the nice things about working with a shirtmaker is that you can often get things made bespoke for not much more than what you’d pay for high-end ready-to-wear. That not only includes dress shirts, but also things with similar constructions – shirt jackets, pajamas, and dressing gowns. The only exception might be silk gowns, which are apparently better off-the-rack. 

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