Casualwear for Tailored Tastes

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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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To be honest, I’m normally not that keen on custom-made casualwear. I don’t think casual clothing has to fit so precisely – most of the time, it looks better if it doesn’t, otherwise you can look a bit uptight. Here, however, there’s a real benefit. Stoffa’s made-to-measure program takes care of some simple, but important, details. The sleeves are cut to the right length; shoulders set to match your natural shoulders; and the front/ back balance adjusted so the coat hangs correctly. These aren’t things you can easily alter in ready-to-wear, especially for leather jackets, but the result is something that looks more tailored. 

This is especially useful for Stoffa since they specialize in the kind of casualwear that sits between true sportswear and formal clothing. You can wear their outerwear with dark jeans and canvas sneakers, but their real advantage is that they can be used in lieu of a sports coat. They look just as natural with dressier items – anything from spread-collar button-ups to Italian knitwear, pleated wool trousers to flat front chinos, leather derbies to penny loafers. Just like Stoffa’s softly constructed overcoats, these are easy to dress up or down as you need. 

To be sure, Stoffa isn’t the only company that specializes in this sort of thing. Loro Piana and Brunello Cucinelli have made a fortune selling these kind of clothes. I just think Stoffa’s designs are more interesting. This flight jacket has a nice, slightly cropped, rounded silhouette that’s reminiscent of the originals, rather than the slimmer, form fitting jackets you often find elsewhere. The large, swooping collar looks great when worn up and the oversized hip pockets lend some nice visual interest. Similarly, their asymmetric jacket has all the ruggedness of a double rider, but is designed with a softer edge. I particularly like how the wide lapels look when the two-way zipper is worn higher up on the chest (see the first few photos below).

For younger guys who like Italian tailoring, Stoffa seems like the perfect casualwear brand. It has the precision of custom clothing, the ease of Italian sportswear, and just the right balance between classic style and something more interesting. You can wear it as daring or conservatively as you wish (see some of Stoffa’s customers on Instagram, such as @andreasweinas, @maxymylyan, and @mdunhoff, who are pictured below). If you have a wardrobe full of tailored trousers, one or two of Stoffa’s outerwear pieces will automatically give you a weekend wardrobe. And if you need some extra trousers, Stoffa sells those too. Only downside: since the clothes are made-to-measure, you can only order them at trunk shows, although accessories are available online. 

(pictured above: Stoffa flight jacket in brown suede; Inis Meain linen sweater; Ambrosi bespoke trousers in H&S’s Crispaire wool; and JM Weston 180 penny loafers in dark brown calf leather)

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