Thanks to its versatility, the t-shirt has been a style staple since the middle of the 20th century. You can exercise and do chores in a t-shirt, and you can also wear it as part of a smart casual get-up for a first date.
I love t-shirts. It’s what I wear most days working from home.
For most of my life, I never tucked in my tees.
Like many people my age, I thought tucking in your t-shirt was something that only your dad or the dorky kid at your school who had no fashion sense did.
Well, I don’t know if there’s something that happens in brain development when you hit 40, and turn into your father, but I’ve been tucking in my t-shirt a lot more these days.
And I’ll be damned; I think it can look pretty sharp in certain situations. Even if you’re not middle-aged or someone’s Pops.
Below, I offer some guidelines that I follow when tucking in my t-shirt so that the vibes it gives off are more 1950s Marlon Brando than 1990s Bugle Boy.
The Evolution of the Tucked-in T-Shirt
While we wear t-shirts as a regular piece of clothing these days, they were originally underwear. Because they were underwear, men would tuck their t-shirts into their briefs or boxers to create a seamless undergarment beneath their outer clothes.
During WWII, GIs would often remove their buttoned uniform top and just wear their undershirt with their uniform trousers. They kept their tee tucked in to maintain a clean, disciplined look even though they weren’t in full uniform.
After WWII, veterans continued to wear their undershirts with trousers while working around the house. They kept their t-shirts tucked in because, well, that’s how they’d done it during the Big One.
That’s how most men in the United States wore their tees from the 1950s onward: tucked in.
As time marched on and style became more casual in the U.S., more and more men stopped tucking in their t-shirts. Wearing their t-shirts untucked was a way to separate themselves from the more uptight generation of their parents. Contributing to the trend was the fact that fewer men served in the military after the Vietnam War, and thus didn’t get into the tucked-in tee habit while in the service.
There was a short resurgence of tucked-in t-shirts in the 1990s, but then it faded along with Beanie Babies.
You’re starting to see more people — particularly young people, of both sexes — tuck in their t-shirts again. A lot of it is driven by Gen Z and Gen Alpha’s nostalgia for the 1990s. My ten-year-old daughter tucks in her t-shirts (emblazoned with the Vans logo — didn’t see that resurgence coming either). She loves that “90s vibe.“
The Benefits of Tucking in Your T-Shirt
Since I started tucking in my tee more often, I’ve discovered three benefits to the practice:
A tucked-in tee accentuates your v-shape. Having the masculine v-shape — broad shoulders that taper to a narrow waist — is attractive. When you tuck in your t-shirt, you accentuate your v-shape; it gives definition to your waist and makes your shoulders look broader.
A tucked-in t-shirt looks put-together. A tucked-in t-shirt provides a clean line between your torso and your legs. It looks a little sharper than an untucked tee, which bunches and wrinkles as it drapes over your waistband. When you tuck in your t-shirt, it looks like you mean business.
A tucked-in t-shirt is practical. Your untucked t-shirt can get snagged on things in your environment. When your t-shirt is untucked, you no longer have to worry about that. This is why I’ve even been tucking my t-shirts into my gym shorts when I work out.
Guidelines for Tucking in Your T-Shirt
Get a properly fitting T-shirt. A t-shirt that is too big won’t look good tucked in. It will give you that early 1990s Bugle Boy dork look. You also don’t want to go too tight either. We’ve got the guidelines for proper fit here.
Note that a tucked-in t-shirt looks best on those with a fit physique. If you’ve got a paunch, a tucked-in tee will only accentuate it, and you’ll probably want to keep your shirt untucked.
Keep it simple. Opt for t-shirts without prominent patterns, text, or busy designs. Go for simple stripes or a solid color. It will just look sharper. That doesn’t mean you can’t ever tuck in a graphic tee. I’ve got a few graphic tees that I tuck in occasionally, but the designs are simple.
Stick with long pants for your bottom garment. I’ve tried tucking in my t-shirt with a pair of khaki shorts and it didn’t look good. Too 1990s dad-ish. Stick with tucking your tees into long pants — jeans and chinos. The one exception for shorts that I make is when I’m working out. Tucking my tee into my shorty gym shorts makes me feel like a Golden Era bodybuilder.
Layer with a jacket. Layering your tucked-in t-shirt is something that I like to do. It adds some depth and interest to your look. I like to wear a cotton field jacket when I tuck in my t-shirt. A jean jacket, chore coat, or unstructured blazer would work as well.
Get a cool belt. Wearing a cool belt gives you an excuse to tuck in your t-shirt: you’re tucking in your tee so people can see your rad belt. My go-to belt when I tuck in my t-shirt is the Cowboy belt from Zilker (that’s what I’m sporting in the left pic above). I also like to rock a thicker, more traditional leather belt, which has a cool Thunderbird belt buckle that I found on eBay (right photo). Besides adding some visual interest to your tucked-in t-shirt fit, a belt also accentuates your waist a bit more, enhancing your v-shaped silhouette.
Like I said above, I don’t tuck in my t-shirt all the time. But it’s nice to have it as a styling option to mix into my get-ups. Give it a try yourself, and see if it just might be one of those things that Dad got right.
