Far and away, the nicest pair of shoes I’ve seen were on Will Boehlke, the former writer and editor of A Suitable Wardrobe. Will was wearing them when I bumped into him five years ago at a hotel. He was coming out of a fitting and I was going into mine. As we passed, I noticed he was wearing some chocolate brown, glazed alligator penny loafers, which I later found out were specially made for him by George Cleverley. I never really considered exotic leather shoes up until then, but since seeing them, I’ve always wanted a similar pair for myself. 

The problem with exotic shoes – particularly those made from alligator or crocodile – is you don’t know if you’ll like them until you try them. And prices here will range from the merely to the horribly expensive, as lower-end exotics aren’t usually worth buying. Anything affordable will be made from caiman, which is a small, Central American reptile that’s a close cousin of American alligator. Caiman leather is cheap, but it’s also not terribly great. Scaly, wrinkly, and tough, it starts off ugly and only gets worse with wear. Roje Exotics has a good video demonstrating the difference between quality crocodile skins and caiman. 

If an affordable pair isn’t made from caiman, then it’s likely constructed from the less desirable parts of an alligator or crocodile hide – the tail or maybe the sides. What you want is a maker who will cut the uppers from the belly of the animal, as well as do some proper pattern matching, but doing so means fewer pairs of shoes can be squeezed from the hide. And thus we land back at the original price problem. 

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There’s an old adage often passed around by men who use bespoke tailors: don’t stray far from the house style. And for good reason. The best tailors specialize in certain looks, which they’ve carefully perfected over the years. Just as you wouldn’t order French food at Nobu, you shouldn’t ask for an Italian jacket from an English tailor. Even if he or she is willing to make it for you, it probably won’t look very good. 

Sometimes, however, under the right hands, straying works. Last year, George Wang at BRIO told me about a new project he’s been working on with Hong Kong tailoring house W.W. Chan. They specialize in clean, classic, British-influenced cuts, but are also a bit more flexible than other tailors in terms of what they’re willing to make. 

For the last couple of years, George has been working with W.W. Chan to create a distinctive house style for his store. When I met up with him last January, he brought a sample jacket, which was maybe it in its third or fourth iteration. “You can’t just give a tailor a big list of changes,” said George. “You have to see how small changes affect the look here and there through each commission. Plus, tailors can be set in their ways, so it’s easier to make these changes in piecemeal steps.”

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John Seabrook, a staff writer at the New Yorker, penned a great article seventeen years ago about the genius of Helmet Lang. In it, he writes about his search for casual clothes in a world where casualwear has come to mean anything and everything. Active Casual, Rugged Casual, Sporty Casual, Smart Casual, Dressy Casual, Business Casual. Some of the names have changed (athleisure is just “active casual” today), but the genres persist. 

The thing that makes Helmet Lang special, Seabrook writes, is that he does upgraded versions of everyday basics. Things that are easy to adopt. An excerpt:

Helmut Lang, the Austrian-born designer, seemed to understand exactly what I needed–a uniform for the new casual world. I bought some more of his clothes: a ribbed cotton sweater that didn’t stretch like my other cotton sweaters; a few pairs of khakis, which had a pleasingly crisp finish; a denim shirt; a woollen sweater in a beautiful straw color; and a pair of jeans. They were intelligent clothes, designed for both work and play, which increasingly seem to be performed in the same outfits.

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For guys who have been interested in tailored clothing for a while, there’s been a lot of interest lately in how to dress more casually. And while there are many ways you can dress down a sports coat, even the best strategies will leave you looking a bit formal. Christian Chensvold put it well ten years ago when he said tucking in a pineapple print shirt into some old khakis nowadays can make you look overdressed in most cities. 

The problem with casualwear, especially for guys who are mainly interested in tailoring, is that the available options often fall into two categories. On the one hand, you have the sort of stuff that works for almost anyone – J. Crew and Brooks Brothers, for example, but those are admittedly a bit boring (something like what a suburban dad might wear, even if a moderately stylish one). Then there are things I think are more exciting, but they can feel niche. I’ve been wearing Margiela’s five-zip leather jackets with slimmer jeans and side-zip boots a lot lately, but that kind of combo isn’t to everyone’s taste. 

Last month, however, I bought my first big item from Stoffa: a dark brown suede flight jacket made with a removable, beige shearling collar. I’ve written about the company before. My friend Agyesh, who founded the company two years ago, worked for Isaia before starting his own label. At Stoffa, he offers a range of accessories, including some wonderful scarves that have to be handled to be appreciated, as well as custom-made outerwear and trousers. 

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The heart of spring/ summer style for me is a good pair of slip-ons. My usual go-tos this time of year include penny loafers – worn with soft sport coats and button-down collars – then camp mocs whenever I’m in denim. 

Lately, however, I’ve looking for a pair of leather slippers. Something dressed down from traditional leather shoes, but more sophisticated than beach-ready espadrilles. Without the ornamentation that comes with penny loafers, tassel loafers, and embroidered Prince Alberts, these feel a bit more causal and contemporary. Something to wear when you’re hanging out at a local cafe or strolling down the boardwalk with friends. 

Antonio Ciongoli, the talented designer behind Eidos, frequently uses leather slippers in his lookbooks. They’re often paired with smartly tailored chinos or drawstring linen pants, as well as striped Breton shirts, long popovers, and loose-fitting pullover jackets. Unionmade recently used the same slippers in a seasonal presentation (lots of shorts and casual summer outerwear here). And Yasuto Camoshita below shows how great slip-ons can look with tailored clothing. 

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The Japanese are famous for their takes on American and Western European clothing – including vintage reproductions made to a fanatically high level of historical accuracy, as well as modern, whimsical interpretations on the classics. Much of what gets exported, however, is casualwear. Today, you can find dozens of retailers for niche Japanese brands such as Visvim, and Kapital, but few stocking anything that approaches tailoring. 

Ring Jacket is one of the few exceptions. As a brand, they’re relatively new, although they have deep roots. For most of the company’s 60+ year history, they’ve operated as a private-label manufacturer for top-end Japanese labels. As the story goes, in 1954, Jhoichi Fukushima decided to open a factory to produce the kind of soft-shouldered, Ivy Style suits worn by President Kennedy (and were popular in Japan at the time). In the 1980s, as Italian tailoring became more popular, they shifted to more Continental styles – still soft shouldered, but with wider lapels and rounder silhouettes.

Today, under the leadership of Kunichi Fukushima (Jhoichi’s son), the company specializes in a sort of neo-classical, Southern Italian look. In the US, they have four models – two for suits, two for sport coats. Most of what you’ll find on the racks, however, is the 184, which is something like Ring Jacket’s house style. The jacket is softly tailored, with a full canvas built in, but little to no padding. The shoulders are somewhat trim; the body short and slim fitting; the gorge high. I think it’s a more flattering cut for those who like brands such as Boglioli. 

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Lookbooks don’t always have to be instructive. Especially for casualwear brands, they’re more often than not meant to serve as style inspiration – showing the idea or spirit behind a collection, rather than telling you how to wear something. 

For the last year, however, The Armoury has been putting together seasonal presentations that feel both fun and grounded. Even if the looks are at times a little bold, many can be tweaked here and there to fit modern life. Last season, they did something in conjunction with illustrator Fei Wang (aka Mr. Slowboy). This season, they shot something inside one of their Hong Kong stores. 

There are lots of great takeaways here. The main one is how easily a suit or sport coat can be dressed down with a pair of slip-on shoes, whether they’re tassel loafers, penny loafers, or those Belgian-esque styles from Baudoin and Lange. Similarly, just like how tweed sport coats can be worn with the right pair of jeans in the winter months (I like Drake’s for these purposes), you can do the same thing with linen jackets on warmer days. The one below from Ring Jacket is cut a little trimmer and softer, which makes it easier to bridge the gap in formality between tailored clothing and denim. 

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There’s a pretty narrow window for when you can wear a spring scarf. And that time is basically now until the end of May – when the weather can be wildly erratic. Crisp mornings are followed by warm afternoons and cool evenings, with a constant chance of spring showers or gusty winds throughout. On those days, having a small, easily packable accessory that can keep you warm isn’t such a bad idea. 

I also think men look better with a bit of neckwear. Bruce Boyer said something similar in his book True Style, which he opens with a chapter on scarves: 

Call it what you will – ascot, cravat, stock – the scarf at the throat is the tested and true answer to the naked neck. It is also the answer for all those baffling formal but “dressed down” occasions when a coat-and-tie are too stuffy, but slacks and a polo shirt are too scruffy. A scarf at the neck provides the right accoutrement to a cashmere cardigan, tweed jacket, navy blazer, or summer sports coat. Nothing so exactly achieves the air of casual elegance, of sporty self-confidence, as a mannerly fold of fine silk or lightweight cashmere with an open collar. 

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If you’re interested in bespoke tailoring, and have a soft spot for Neapolitan style, here’s some interesting news. Gianluca Migliarotti, the director behind O’Mast, is forming a new company with two of his friends – Gennaro Formosa and Lino Pommella. Together, they’re starting Pommella Napoli, a new tailoring house specializing in Neapolitan trousers. The most exciting part: they’ll be touring the world, bringing Neapolitan style to international customers. 

Gennaro, as some may know, is the owner of Sartoria Formosa. He’ll be handling the new company’s business logistics, although the two tailoring houses will remain separate. Gianluca, on the other hand, will handle marketing, communications, and customer service for trunk shows. 

The star of the business, as you can probably guess from the company’s name, is Lino Pommella. For the last ten years, he’s been the head cutter for trousers at Rubinacci. Having learned tailoring from his father, who himself was a trouser cutter his whole life, he’ll now be the head cutter at his own firm. I’ve handled some of the stuff he’s made at Rubinacci – and while it would be a mistake to conflate the two companies – the cut was very nice. Slim, but still classic, with a pitch perfect fit around the back. 

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It’s hard to imagine now, but Savile Row used to be a lot stuffier than it is today. It took tailors such as Tommy Nutter and Richard James to transform what used to be a very hush-hush gentlemen’s quarter into a hipper, edgier place that attracted the likes of Mick Jagger and The Beatles. Guys who love classic menswear love to turn their nose up at “fashion,” but if it weren’t for new ideas and a younger clientele during the ‘60s and ‘90s, who knows what would have happened to the trade. 

One of the areas that excites me most in men’s style is this intersection between craft and fashion. Davide Taub, head cutter at Gieves & Hawkes, for example, shows an inspiring sense of open mindedness when it comes to design (rare, frankly, in the tailoring business). He’s said in interviews that he admires Rick Owens and his own work reflects an uncommon level of creativeness. Similarly, Savannah Yarborough was a designer at Billy Reid before she started her own bespoke tailoring firm. She combines the oldest of traditional tailoring methods with contemporary design in order to make unique, one-off leather jackets that have a Southern rock ‘n roll edge. 

Another craftsman in this regard is Sebastian Tarek, a bespoke shoemaker in London. Sebastian is one of the outworkers who makes for the city’s West End firms. One the side, however, he also has his own shoemaking business, where he produces handmade, bespoke shoes in styles that are better suited to skinny jeans than tailored trousers. 

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