How to Wear Sneakers with a Sport Coat This Summer

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Picture this: you’re packing for your summer vacation. You’re trying to pick the ideal shoe – something you can wear sockless while carrying your towel bag down the rocks to the beach, but something that also works in the evening when you put on a jacket and trousers – or even a suit.

What you want is a white canvas sneaker.

Before you accuse me of telling you lies, let me assure you that wearing sneakers with a sport coat is a fine thing to do, and it’s pretty common in places that aren’t the USA. Arianna tells me that she can remember seeing Fiat managers wearing sneakers with their charcoal and navy suits, and of course sneakers are all over Pitti Uomo. You don’t have to go full-on captain of industry or Pitti peacock-hashtag-menswear to make the sneakers work, though – you just have to avoid the pitfalls of looking like a Disney star or a child playing dress-up.

Let’s talk about those pitfalls first. If you’re going to wear sneakers with a sport coat or a suit, and you’re after inspiration on how to do it, the first images you’ll find on the internet will probably be of either actor-slash-model types standing on the red carpet wearing really tight clothes and designer high-tops, or waifish Scandinavian dudes wearing black suits with white leather slip-ons inside their million-dollar Youtube-content-creator-slash-graphic-design-influencer offices.

Not that I’m jealous.

The point is, a lot of people try really hard to build their tailored outfits around the sneakers they’ve chosen. Along the way, they often pick up a few more trends – really tight trousers, gingham shirts, skinny ties – and this has the effect of making them look, well, childish. Like they’re playing dress-up. That’s not what you want! What you want is to wear sneakers with a jacket and trousers and look like a well-dressed adult.

So, instead of sizing down on everything you own, treat a pair of canvas plimsolls the same way you would a pair of loafers or espadrilles. Wear them sockless, with a lightweight trouser that’s hemmed at the ankle (or even just above, if you’re really feeling the warm weather look). If you’re wearing a suit, it’s probably safest to go with one that’s obviously made for the warmer weather – say, a cotton number in khaki or even green, or natural linen if that’s what you’re after, but an odd jacket and trousers will work just as easily.

There’s no need to buy something fancy, either. In fact, that sort of goes against the intent. White canvas plimsolls from brands such as Vans or Superga will look great, but if you’re really wanting to branch out you could try a leather slip on from Common Projects or Buttero. In all cases, stick to low-tops. Once you’ve picked your sneakers, the next and final step is to put them on your feet and never think about them again. After all, you’ve a life to enjoy.

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Perfect Spring Style: the Popover Shirt

As further proof that fashion – and men’s fashion in particular – operates entirely in cycles, I don’t think I’ve ever seen as many popover-style shirts at so many different retailers as I have this spring. Although it never disappeared, the popover hasn’t exactly been a mainstay of menswear since the 60’s, when Gant made up the style in oxford cloth and it became an instant favorite of the Ivy set. Certainly, there have always been men who’ve worn them, especially in Italy (as opposed to elsewhere in Europe) – Gianni Agnelli was, after all, well known for favoring them – but especially in America, they’ve been a purely casual item to be found mostly at Ivy retailers (Brooks Brothers, Gant, occasionally J. Press), and mostly made up in Ivy colors and fabrics.

The thing is, the popover wasn’t a new style when Gant “introduced” it to the East Coast (besides, Agnelli appears to have been wearing them – with a spread collar as opposed to a button-down collar – by that point). It’s full-length buttoning that’s relatively new, and which only appeared in the mid-1800’s. If you’ve ever browsed antique shirts, you’ve probably noticed that most of them – whether they’re the sought-after French workshirts or the “formal” English pieces – only sport half-plackets. It was only after the introduction of the full placket that popovers slowly disappeared across most of Europe and America.

Part of the recent dearth of popovers, at least in terms of contemporary fashion, must surely be due to our decade-long obsession with Tight Things. Since popovers must be pulled on over the head, they require a bit of extra room in the body to accommodate waving arms and wide shoulders, and I can only imagine that said extra room was anathema to most brands attempting to ride the slim fit wave. In addition, the view of popovers as a purely casual item didn’t do much for their popularity, but as tailored clothing continues to become less and less important to the daily lives of most men, it appears that popovers are – at least in some places – back on the menu, so let’s talk about how to wear them.

First, it’s easy to find casual popovers cut to a length that’s meant to be worn untucked. If you want to channel Ivy style, add a pair of chino shorts, a woven belt, and some penny loafers, and you’re set for summer on the Vineyard.

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Spring and summer are, in my opinion, the perfect seasons for popover-wearing. The slightly relaxed cut, especially when done in a linen or linen blend, is great for warm weather, especially as a vacation shirt. That’s because it’s nice-looking enough that you can wear it out to dinner, but not so nice that you feel bad bundling it up with a beach towel. And you don’t have to be channeling the preppy thing, if you don’t want to. Roll up the sleeves, put on a pair of Vans, and you’ll look just great. Or do as men such as Gianni Agnelli and Yasuto Kamoshita do (Kamoshita also often wears polo shirts under his jackets), and wear yours under an odd jacket or with a suit. The point is that no matter the style you’re after, a popover is a great shirt to have in your wardrobe.

If you’re looking for casual options, affiliate Need Supply is a good place to start, as are brands like Gitman Vintage. If you’re open to wearing a band-collar shirt, those aren’t hard to find at all. Tailoring-friendly options are a bit less easy to come across, although Kamakura offers their own take on the Ivy classic, as does Brooks Brothers. Eidos has been known to offer both band-collar popovers and long-sleeve henleys in the past, and Ralph Lauren’s stock rotates regularly. Amusingly, Gant’s own popovers come and go as well, so you may have to do a bit of searching. If you know exactly what you’re after, Proper Cloth also offers popover plackets as an option.

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It just so happens that affiliate No Man Walks Alone stocks this great linen popover from G. Inglese, which would look pretty darn good with one of those Solaro suits we keep talking about. Wear it with a tie or without, with laced shoes or loafers. However you decide to wear it, wear it in good health, and enjoy the good weather.