There are a lot of great menswear videos, but for my money, none beat this clip of President Lyndon B. Johnson ordering six pairs of summer trousers. It was recorded in 1964, like all White House phone calls at the time. In it, you can hear the President talking to his tailor, Joe Haggard, about how he’d like his new trousers made in very specific, anatomic detail:

“Another thing is the crotch, down where your nuts hang. It’s always a little too tight. So when you make ‘em up, give me an inch so I can let them out there – cause they cut me; it’s just like riding a wire fence. These are the best I’ve had anywhere in the United States, but when I gain a little weight, they cut me under there. You never do have much margin, but see if you can’t leave me an inch from where the zipper (burppp) ends, round back to my bunghole.” 

I’ve never specified bunghole measurements to my tailor, but I have gotten pretty picky about my trousers over the years. One of the nice things about custom-made clothing is that you start from scratch. Details that you never really considered in ready-to-wear can now be fussed over. Should you get flat fronts or pleats? Belt loops or side tabs? What about Daks? When are cuffs appropriate? A lot of this is personal preference, but in case anyone found it helpful, I thought I’d lay out my own logic for these things. 

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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. 

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Japan has one of the most vibrant communities of bespoke tailors and shoemakers in the world, but you may not know it if you live in the US. Few get written about on English-language blogs, and fewer still visit the US. For most of us, it’s hard to find information about Japanese artisans – and nearly impossible to order things. 

A lot of this has to do with the size of your average Japanese firm. It’s easier for larger tailoring houses on Savile Row to travel – they have more well-recognized names, and if one or two customers drop out, it doesn’t make much of a difference to their overall business. Things are different for smaller companies. A few dropped orders can financially kill overseas trips, and they typically don’t have the support staff necessary back home to scale up. These are the same reasons why you don’t see many traveling Italian tailors – most of the firms are small. 

It’s too bad since a lot of Japanese tailoring is great. Take Noriyuki Ueki, for example. He started his career at Ring Jacket in 2001, before moving to Naples four years later to apprentice at Sartoria Dalcuore, working under master tailor Antonio Pascariello. In 2008, Ueki moved back to Japan to start his own firm, Sartoria Ciccio, and recently opened his owned atelier in the Minami-Aoyama district of Tokyo. 

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Every season, there are one or two things I regret having missed out on. Last season, it was this Melton wool “traveler coat” from Kaptain Sunshine. It’s a long, raglan-sleeved overcoat made with lots of cool details – including a flapped patched, ticket pocket set just above the hips; equestrian-inspired leg straps hidden in the interior; and a perfectly cut collar that looks great when worn up. Most of all, I love the silhouette. Comfortable fitting and slightly oversized, it’s a refreshing take on men’s outerwear in this slim-fit age. You can see my friend Kyle wearing it here with a chunky, cabled turtleneck and some light washed jeans. 

If you’ve never heard of  Kaptain Sunshine, don’t worry – they’re a relatively new label, having just started in 2013. Their designer, Shinsuke Kojima, was one of the founding editors of Huge, a popular Japanese magazine that sadly folded just two years ago. Having left the publishing business, Shinsuke now designs his own menswear line, Kaptain Sunshine, as well as Woolrich’s Japanese collections. 

Like many other Japanese brands, Kaptain Sunshine takes inspiration from vintage Americana, militaria, and outdoor wear. A lot of this comes from Shinsuke’s love for vintage clothing, which he’s been collecting since he was 15 years old. As a teen, he used to rummage through Tokyo’s dustier thrift stores for vintage Levi’s, varsity sweaters, and beat-up military parkas. These days, you can still find him on the weekends at Suntrap, a premier vintage outfitter in Tokyo, which Shinsuke cites as one of his favorite shops. 

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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. 

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If you’re as big of a Ralph Lauren fan as I am, get ready to crap your pants. 

My friend Zach is an inveterate thrifter, with an eye for quality and style. So when he lost out on British Ventile smock recently, he was understandably pretty disappointed. 

Looking through the feedback section for that item, however, he noticed a familiar name: John Wrazej. 

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It would be too much to say that the suit is dead, but here in San Francisco, you’d struggle to find occasions to wear one. More and more people nowadays are dressing down for the office, even in industries where client-facing interactions have historically required more professional wear. My prediction is, in another generation or so, dark suits will only live on through weddings and funerals – the last places for traditional clothing in any society. 

My solution so far has been to rely on sport coats, or at least informal suits made from casual materials (e.g. cotton, linen, and corduroy – which, if I were to be honest, are mostly worn as suit separates). Even if a dark suit today is a rare sight, few people bat an eye at more casual forms of tailoring. You can wear a sport coat to a nice bar or restaurant, or depending on where you work, even the office. 

The problem is that none of those options really look as good as a traditional two-piece, so this year I’m hoping to get what I call an “in-between” suit – something smarter than a sport coat, but more casual than traditional business dress. Bold, patterned flannel is nice for this sort of thing, but I’m hoping to start off with wool gabardine. 

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I really want to go to Italy this year to commission some things from a few tailors. There’s been a lot of talk lately about how bespoke tailoring is on the decline – things aren’t as good as they were a generation ago and tailoring shops are slowly being converted into ready-to-wear brands. There’s a kernel of truth in that, but there’s also a lot of new talent in the trade and inspiring work being done. I’m not as down on traditional crafts as some of my friends. 

It is true, however, that the older generation is starting to retire, especially in Italy. And when they go, they’ll take with them their sense of style. Not that the younger generation is bad – the two are just different. The older generation is more inspired by 1950s fashion, while the younger generation makes things a bit flashier and, at times, more form fitting (with exceptions). I like both, but there’s something special to me about that older generation look. 

I thought about this other day as I was looking through these photos of Kentaro Nakagomi, owner of the new outerwear label Coherence. Kentaro gets some of his things from Loris Vestrucci, an older Florentine tailor who was a legend of his time, but is rarely talked about online. Unfortunately, Vestrucci is semi-retired now. He’ll still make things for some of his clients, but he won’t take new customers. Trust me, I tried. 

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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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