On t-shirts with tailored clothing.
It doesn't need to be fancy.
I was asked in a style interview about my thoughts on t-shirts with tailored jackets, specifically regarding the fineness of the fabrics and scale of the neckline. My answer was edited a bit when the article was posted, which is fine as the interviewer likely thought he was doing me a favor by sanitizing my somewhat dismissive tone. I’ve been contemplating recently why it bugs me when folks get hung up on the minutiae of things like that when it comes to putting casual clothes together. I run a business that is considered by some to be the standard bearer of classic tailored clothing, with a rules-guided approach to dressing. So, it may seem hypocritical to roll my eyes at a particular nitpick while I’m advising clients in proper ways of dressing – like how it might not be the best pairing to wear a grenadine tie (open weave, arguably summery) with a flannel suit (wintery).
The reason I think this topic is different is due to the formality of what you’re wearing, and your personal approach to clothing.
If you’re putting a daytime formal outfit together for work or an event with a socially expected dress code, the devil really is in the details. The proportions of the clothing should flatter your figure, the shirt collar should frame your face well, the tie should be properly knotted with a dimple, the socks and shoes should be dark and harmonious with the suit, and if you’re wearing a pocket square the colors should complement the entire outfit rather than match the tie.
When you’re wearing a t-shirt, the rules of formality and texture kind of go out the window. You're already essentially breaking the rules of tailored clothing by pairing a tailored jacket with something as casual as a t-shirt, and you’re in the realm of personal style. I rarely pair a particularly elegant suit with a fine luxury tee, as it can feel like I’m trying too hard to dress it down.
Simon Crompton of the website Permanent Style starts his piece on this topic the way I’d expect, highlighting a strictly rules based approach. Essentially, he suggests a fully fashioned sweater-style collar is most appropriate to bring the formality levels closer together. I was surprised though to see him continue from there and acknowledge a much more casual approach, which is what I’m getting at here. One of my favorite style images is of Harry Anderson in a donegal tweed jacket over a Mickey Mouse sweater:
It’s such a great look simply because it’s fun. The jacket looks like it was tossed on, like it was the closest thing in his closet and could just as well have been a windbreaker if that’s what was nearer at hand. Harry looks cool here because his outfit doesn’t look overthought. If it’s a look you want to emulate, try his approach with jeans and a more casual sport jacket, and save the strict rules for strict clothes.
Here’s a few ways I enjoy doing it-
