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Over the last few years I’ve migrated from a younger looking sense of style, to a much more grown up (some would say older) look. One of the things I’m just not that comfortable with anymore is going out on a Friday or Saturday night with an untucked shirt. It feels a bit sloppy and too young. But when I tuck it in I feel too business casual if I’m wearing chinos, and almost cowboy like if I’m wearing jeans.
Any suggestions? And do women view guys who leave their shirts untucked as younger or less polished?
Until I read your email, I hadn’t spent much time thinking about whether I prefer a tucked or untucked shirt on a man. Now that I’ve dived into these murky waters, I’m consumed with thoughts of tucking or not tucking (um, is it just me or does that sound…suggestive? I think I’ve been spending too much time with you guys). I took a look around at some of the usual suspects for men’s style and clothing, hoping for some unofficial rules that I could pass on. Here’s what I found:
Mostly, button-down shirts are shown tucked in. This look is, as you pointed out in your email, undeniably business casual. But I found a couple examples of untucked Oxfords that still look sharp. In this example, the bottom of the shirt stops right at the crotch, so it’s not oversized. But I think what really makes this look successful is that the shirt is pressed from top to bottom.
A lot of times when we see an untucked button-down, it’s because it was formerly tucked in and now, after too many Jack and Cokes, the shirt has slipped out of the pants, and has that wrinkled accordion pattern on the bottom quarter of the shirt. If you wear a well-fitting button-down, iron it, and purposefully wear it untucked, it can work.
Polo shirts are shown untucked. BUT, this is contingent on the polo fitting perfectly which means that it hits just below the waist band of your pants. If you are wearing a polo that is longer than this, it’s probably going to look sloppy and too big worn untucked. This, for example, looks an inch or two too long to be worn untucked.
I did notice a trend, favored by one brand in particular, in which shirts of all different kinds are shown with a casual it’s sort of tucked in but sort of not style. See this page. Two or three inches horizontally across the front of the shirt are just barely tucked in while the sides of the shirt are resting at the waist, and the back might be half untucked/half tucked. It looks good, there’s no denying that. It shows off the lean physique of the model, highlights the waist detail of whatever pants are being worn, and gives off a too cool to care what’s happening with the bottom of your shirt vibe. I have to wonder if that’s a sustainable tucking situation, though. Would the shirt stay half tucked/half untucked for the whole day? Or would you be constantly rearranging?
To answer your final question, Owen, no, I don’t think women view an untucked shirt as a sign of youthful ignorance or sloth. As I’ve said before, you can control much of how others perceive your style by the purpose with which you put yourself together. If you have a neatly pressed button-down that fits well and is worn untucked with jeans, women will be aware that you’ve made that choice purposefully, not that you’re too lazy to bother with tucking in your shirt. Whereas Uncle Joe on his eighth Jack and Coke, dress shirt askew, making an ass of himself at your sister’s wedding, will be presenting a different impression.
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