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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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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