Not many people know this, but a few Northampton shoemakers will allow you to order almost anything from their archive. And with histories that sometimes stretch back as far as a hundred years, there are a lot of shoes to choose from. 

One of the better programs is at John Lobb – the one based in Paris, not London. As some readers know, there are two Lobbs. The original, situated on St. James of London, operates as a bespoke-only firm. In 1902, they opened an outpost in Paris, which was later sold to Hermes. When Hermes acquired the shop, they got with it the rights to use the Lobb name for a ready-to-wear collection (which debuted in 1982). That’s the John Lobb most people are familiar with, even if it’s relatively much younger. 

The Hermes-owned Lobb is a complicated business. There’s the ready-to-wear line, of course, then an exclusive – and frankly very expensive – bespoke program. Their bespoke shoes have a subtle French sensibility, but are still very classically English in taste. Lovely footwear, but with prices that start around $7,500, they’re prohibitively expensive for the most guilty of spendthrifts. On the upside, the Lobb store tells me they’ll fly their fitter out to meet any clients in the US – even if yours is the only order in that city. 

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No shoe style is more controversial than the bit loafer. Part of is that slip-ons have forever held a slightly louche appeal – and none moreso than the snaffle bit variety. Up until the First World War, it was the English who set footwear standards, and they favored laced-up oxfords in the city and heavier brogues in the country. It was only until the Americans popularized penny and tassel loafers that that slip-ons gained greater acceptance. And even then, they’ve always been looked at with a bit of suspicion. Today, a conservative oxford will say little about you. A penny or tasseled loafer, on the other hand, comes with some preppy connotations. 

Bit loafers suffer from an even greater problem because they’re associated with some of the worst types of dressers – flashy guys in overly slim-fitting suits, with their shirts unbuttoned to their sternum. Or arrivistes who wear them with contrast collars while, presumably, fantasizing about being the protagonist in 1980s movies about finance. If the term tassel loafer can be used as part of an epithet – to quote that famous 1993 line where George Bush complained that Bill Clinton was supported by “every lawyer that ever wore a tasseled loafer” – just imagine the pretentious bravado that can be assumed of people who wear metal on their feet. 

Still, I’ve been wanting to get a pair every spring. The iconic Gucci version – originally designed in the 1930s, just as the penny loafer was taking off – looks a lot better with summer suits than an oxford. In fact, that’s the genius of the horsebit loafer. In one of his books, Bruce Boyer wrote of the style: “It was the first shoe that bridged the gap between casual and business wear. This dressy slip-on was refined with fine, lightweight calfskin, a pared-down shape, and a metal snaffle bit, and as such it became avenue-elegant and gained acceptance in corporate board rooms and country clubs alike.” 

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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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