How to Keep Your Shirt Tucked In

Have you noticed how button up shirts seem to constantly come untucked throughout the day?

It seems like, no matter what you do, your shirt will come untucked and look sloppy, especially when you reach your arms above your head.

KK and Jay logoNote: Huge thanks to KKandJay for making this post possible! KK & Jay makes shirttail garters and suspenders for men. Their products are handmade in Brooklyn – very high quality and stylish. Use the code MODMAN for a special discount!

Even fitted, tailored shirts are prone to coming untucked. And no one likes the muffin top look.

So how do you keep your shirt tucked in? Read on for three unique solutions.

How to keep your shirt tucked in

First off, it's important to tuck your shirt in properly. I like to use a technique commonly referred to as the “military tuck” that involves folding the excess fabric of your shirt as you tuck it in.

Unless your shirt is extremely slim (to the point of being restrictive), the military tuck (or some variation of it) is a good idea.

But even if your technique is tucking perfect, your shirt will still come untucked, especially when you reach your arms over your head.

Shirt comes untucked

Every time I reach up to get something…

I don't know about you, but at 5'6″ in boots, I'm reaching my arms up many times throughout the day (to grab a mug from the cabinet or to fix my hair, for example).

So what can you do to prevent your button downs from coming untucked? One of these three things:

Technique #1: Shirt Stays

Also called shirttail garters, these are the best accessories for keeping your shirt neatly tucked in all day long.

Plus, they keep your socks up at the same time. Bonus points for shirt stays!

These things have been around for a long time, and after using them myself, I can understand why. They just work. Better than any rubber belt or magnetic clip.

Shirttail gartersYou simply attach one end of the stay to your shirt and the other end to your socks, and that's it.

Now, I'm sure you have a couple of questions about wearing shirt stays, so I'll try to answer them now:

“Do they fit shorter men?”

Shirt stays are usually one-size-fits-all, and they should work for most shorter men. The garters I have are meant to cover a distance of 14-24 inches.

So, if they distance between the top of your socks and the bottom of your shirt is less than 13″, there won't be enough tension for the garters to do their job.

That said, unless your dress shirts are too long and/or your socks are too high (like over your knee), you won't have a problem.

If you wear mid-calf socks, you'll definitely have enough tension.

“Are they comfortable?”

Yes, they are comfortable. You get used to them very quickly.

“Do you have to take them off to use the bathroom?”

If you're sitting down, you'll have to unclip either the top or bottom of each stay. I prefer unclipping the bottom (the part that's attached to my socks) because it's just one clip instead of two.

“What if I'm getting undressed, you know, in front of someone?”

Worst case, they think the shirt stays are funny. Best case, they find them sexy. I wouldn't worry about this at all!

KKandJay Shirttail Garters

KK and Jay shirt staysThe shirt stays I tried out for this post are from KKandJay, a Brooklyn based company founded by New York City Jew and a west African Ivy-Leaguer who share a passion for menswear.

I spoke to NYC native Jason over the phone and learned about his vast experience with menswear and his passion for helping men look their best.

Together, him and Mohamed Kaykay are on a mission to help men stay tucked – all tucking day.

If you're serious about keeping your shirt tucked in, I recommend trying shirt stays. The next two techniques are better than nothing, but they're not nearly as effective as garters.

Technique #2: Rubber Grips

Some pants come with strips of rubber built into the inside of the waistband.

Rubber strip on pantsI've noticed that many made-to-measure brands offer this as a default option these days, which is great.

If your pants don't have this feature, you can actually add it in yourself, or have a local tailor do it for you.

Many tailors carry rubber grip “tape” that can be sewn along the inside of your waistband.

If your tailor doesn't have any, you can actually buy it yourself (couldn't find any on Amazon, but you can buy it from sewing supplies shops like this one or this one).

While this technique is better than nothing, it's not nearly as effective as shirttail garters.

Speaking of better than nothing…

Technique #3: The “Undertuck”

I'm not sure who invented this tucking method or if “undertuck” is even the correct name, but here's how you do it:

How to tuck your shirt in

Tuck your undershirt into your underwear, then tuck your shirt into your pants. So the layers go:

skin → undershirt → underwear → shirt → pants

That's it. I don't know why this works better than the traditional tuck (i.e., tucking both your undershirt AND shirt into your pants), but it does.

Trust me on this one. Just try it. You'll be pleasantly surprised.

Of course, this won't work if you don't wear an undershirt (or underwear, for that matter).

Then again, you're probably not going commando at the office…right?

Your Tucking Turn

If you use the undertuck and practice proper tucking technique (i.e., the military style tuck), you'll already be in much better shape than most guys.

If your pants have rubber grips, that's an added bonus.

But if you really want to stop your shirt from coming untucked, get yourself a pair of KKandJay shirttail garters (or three).

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  1. Traditional double-tuck doesn’t work b/c the undershirt actually lowers the friction of the overshirt sliding around. It’s like wearing two pairs of socks in the winter – the outer pair slides all over the place b/c the inner pair gives it a smooth surface to slide on instead of sliding directly on your foot. I’m convinced most people do the “undertuck” and just don’t talk about it.

  2. I’ve been undertucking for about 2 years now. It definitely helps streamline my 9 to 5 wardrobe. I highly recommend it (unless you have swamp ass).

  3. I have heard great things about shirttail garters, but do they ruin your shirt and socks faster? I have heard they do which so far has stopped me from trying them. I was wondering if you had noticed unusual wear and tear because of them, how much, and if it is just worth it for that nice streamlined look.

    • I haven’t used them long enough to notice anything. The ones I have don’t have any sharp edges, just a plastic circle that slides into a metal slot. On their FAQ page, KK&Jay says they definitely don’t ruin your shirts and socks.

    • gentlemanwithin says:

      I have a set from a different brand, but the locking mechanism is identical. I wear them occasionally and haven’t noticed any destruction of my shirts or socks.

      The bigger issue is the pulling of your leg hairs. That’s a pain, which after a while you may feel it. But hey, gotta sacrifice one thing for another right?

  4. Cool tip on undertucking; I’ll have to try. Any advice on selection/style of undershirt to best achieve this effect? I feel like I already have problems finding an undershirt that fits well with my dress shirts and ties.

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