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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. 

Nothing defines the American fashion experience more than trying to find the perfect pair of blue jeans. They’re the foundation of any wardrobe outside of tailored clothing, the casual equivalent of gray flannel trousers. This old Australian documentary on Levi’s summed it up best: 

The symbols that tell a story in a twinkling of an eye are usually everyday products, but some are very special. The Eiffel Tower says France, but the little Sony walkman says Japan. The archetypal symbols that yell America are the Coke bottle and Levi’s Strauss jeans. They all enjoy the prestige of being regarded as design classics. […] Film stars, American presidents, student protestors, and rock musicians have all worn the 501. From gold mining through protest, to what they are today, [blue jeans] are the story of the acceptable uniform for non-conformity. 

Some men look great wearing tailored clothing year-round, but I can’t imagine building a wardrobe without blue jeans. They’re practical, hard wearing, and frankly look great. Even Bruce Boyer, the closest thing we have today to an arbiter elegantiarum in classic menswear, occasionally wears a pair. Over the years, I’ve cycled through at least a dozen models trying to find the Platonic ideal. The truth is the perfect pair of jeans doesn’t exist – a lot depends on what other clothes you like to wear. Here are ten models, however, that I think are notable. 

It’s been about ten years since fashion journalist Dana Thomas penned Deluxe. And today, it stands as one of the best books I’ve read on the rise and fall of luxury labels such as Prada and Louis Vuitton. The book is about how the constant search for higher profits has led many old-world luxury companies to give up things that made them special in the first place – a commitment to quality, a focus on craft, and a willingness to innovate in terms of design. It’s not hard to notice that, for consumers in Western Europe, North America, and Japan, these labels have become less and less relevant over the years. 

It’s hard, however, to identify what’s replacing them. My friend Paul Munford, who runs the very smart Leanluxe, likes to say modern luxury companies are centered around a quiet confidence in branding, virtue of product, specialization, and transparency. Think of companies such as Ledbury, Common Projects, and Tracksmith. 

Perhaps. Sometimes I think Paul’s focus is more driven by aesthetic differentiation (e.g. minimalist branding) than actual business models. Plus, luxury is inherently hard to define. The people who were buying Louis Vuittion a generation ago may not be the same people buying Ledbury today. At the same time, that may not matter, as it’s clear a shift is happening. Mr. Porter, for example, is very much a luxury shop – and they don’t carry many of those old world brands. 

For a blog called Die, Workwear, I’m really into Unionmade. The store specializes in hard-to-find workwear, heritage brands, and Japanese imports. Basically the sort of things you’d see in Free & Easy, back when they were still being published, but available in one (very large) boutique. 

They also have some great sales every once in a while, which make their admittedly high prices a bit easier to stomach. Last night, they cut prices in their sale section, where you can knock another 20% off with the checkout code EXTRA20. Shipping is a reasonable $10 for most of the United States ($40 to $60 international). 

You’ll find a lot of good basics here. Gitman Vintage button-downs, striped Saint James Bretons, Wolverine work boots, New Balance sneakers, and the lowest price I’ve ever seen for a staple Barbour jacket. I also really like these light washed Levis jeans, which come in the 1947 version of their 501s (the cut has changed a lot over the years, but the 1947 version is probably the easiest to wear with its slim-straight fit). On a hot summer’s day, I can imagine those being worn with this white Arpenteur camp collar shirt and some Yuketen huaraches. 

Sale season this year is moving along quickly. Mr. Porter just made their second round of price cuts, putting things at 70% off just two weeks after they started their spring promotion. Given the size of their inventory, your best bet is to filter things by size and see what serendipitously pops up. Also worth checking back once a week or so. As people make returns, you can expect to see some items get restocked. 

Some things I think are notable: brands such as Chimala, Camoshita, Eidos, Kapital, and Drake’s are favorites and they have some surprisingly good things still left. I also like these Margiela leather babouches, Margaret Howell linen-wool blend sweater (lovely color); Our Legacy washed jeans; chunky Nonnative ribbed turtleneck; Orlebar Brown swimwear; Engineered Garments folk print shirt; Viberg work boots (blessed be the men with bigger feet), Gaziano & Girling loafers, and suede Valstarino bombers. For this coming fall/ winter, there are some heavily discounted gloves from Dents, just $50 a pair for leather models lined in cashmere. Lastly, don’t forget to check Mr. Porter’s much slept-on house label, Kingsman. The stuff there is often made in collaboration with top-end companies, such as Mackintosh and Drake’s, but will often get passed over because people forget to look. 

J. Crew’s Wallace & Barnes might be one of the most slept-on lines in menswear. Not everything in the collection is great, but if you’re looking for affordable basics, you could do worse than by sifting through the sale section every few months. The clothes have more of a boutique feel than J. Crew’s mainline, are made from better materials, and are inspired by vintage pieces that Frank Muytjens, the company’s head menswear designer, and his team routinely collect for their design archives. 

I recently picked up a couple of their heavyweight flannels (on sale today for $48 with the checkout code SALEFUN). The term heavyweight here might be an oversell, but they’re wonderfully thick and sturdy, yet also soft enough to wear without an undershirt. Like many of Wallace & Barnes’ workshirts, these are triple needle constructed and have a chambray lined yoke to help with durability. For under $50, these feel like the kind of good, honest basics that have mostly disappeared from menswear. 

It’s been great seeing Drake’s develop into a fuller menswear line. Fifteen years ago, most people would have never even heard of the company, even though they’ve been around since the 1970s. For much of their history, Drake’s served as a private label manufacturer located in London’s East End, where they produced classic neckwear for a variety of top-end brands. As the wholesale market has gotten squeezed, however, Drake’s has had to reposition itself – going from a private label manufacturer to a consumer-orientated brand. First came the ties, pocket squares, and scarves bearing the company’s name. Then, in more recent times, they’ve added shirts, sport coats, outerwear, knitwear, jeans, and small leather goods. 

All of this has allowed them to put together seasonal lookbooks – models fitted head-to-toe in things you can find at the Drake’s store. The outfits are somewhat stylized, to be sure, but they’re great for inspiration. 

The new one for spring just dropped on Drake’s site. I particularly like the cream-colored sport coat they put together with navy trousers – a refreshingly modern take on the dark jacket with grey trousers most of us wear. They also have a navy wool seersucker suit, which I think will age better than its cousins in cotton. Cotton suiting can be great in the summertime, but given how it fades, it doesn’t always age well in darker colors. 

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: