I’ve always considered the tshirt-with-tailoring combo to be the sort of look you only find in Monocle, something nice but sort of abstract to my everyday life, like really good public space design in Copenhagen. Or worse, the look was the heir to the early 2000s’ pairing of hoodie with thrift store jacket. Was it just me doing that?
But I’ve finally come around to it this summer, maybe just because it’s hot and I have some jackets that are light as shirts, so wearing a tshirt under doesn’t seem so odd. Although the pairing falls outside what we’d regard as menswear rules, there are some things to keep in mind if you’re just trying it out.
- Like shorts, this is not likely good for the office, unless you have a pretty slack dress code and understanding coworkers. In most offices a tshirt isn’t acceptable, and wearing a tshirt AND a jacket calls attention to itself, something that may or may not be a good move at work.
- The rules of wearing casual tailoring well apply. A jacket with a lot of structure or sharp angles is better matched with similarly formal shirts and accessories–now is the time for the softer, less severe tailoring that’s become more broadly available over the last few years, or a jacket with no internal structure at all, like an Engineered Garments jacket or this shirt jacket. It doesn’t need to be super trim, though–one of the bonuses of wearing a tshirt is comfort so no sense in wearing a jacket you can barely button.
- Pick a decent shirt. We love a basic tshirt but there are creative options out there that can work better in this context, mostly distinguished by fabric. A linen blend shirt, a terry shirt, a henley, or a stripe detail or breton type shirt all make some sense. Neckline also matters–a standard crewneck will fit close to the neck and look a little cleaner (and will be a little easier to wear); a looser neck (but no deep Vs!) might look a little more current.
- Consider casual footwear. Yes, oxfords are for suits, derbies for sportcoats, but if you’re wearing a tshirt with your suit, you’re probably not trying to keep the spirit of Apparel Arts alive. In these situations, a very casual shoe, like a desert boot, Doc Marten-style chunky oxford, or even sneakers or slipons can work better than technically appropriate shoes.
- To tuck or not to tuck? Part of deciding whether to tuck in your tshirt is the length and cut of the shirt. You don’t likely want a tshirt that’s so long it reaches the hem of your jacket; if that’s the case you may need to tuck or at least fold under the hem of the shirt a bit. Although it’s gotten a lot of attention this summer, I’m still not on board with the full tshirt tuck. But don’t get too fussy about it–again the point here is casualness.
