How to Keep Your Shirt Tucked in Neatly

There’s nothing more frustrating than a dress shirt that won’t stay tucked in. Even when the rest of your outfit looks great, the minute your shirt starts bunching up, all bets are off.

You imagine your co-workers staring at your growing muffin top:

“I swear, that’s not my belly…it’s this shirt…I work out, I do paleo, I, I…”

But your billowing mid-section says otherwise. Your “smart business casual” is starting to feel less smart and more casual as the day progresses.

This wouldn’t be a problem if you could magically transport yourself from your house to your desk and NOT MOVE all day. But that’s not realistic. So you keep “readjusting” throughout the day and PRAY no one catches you with your hands down your pants.

Is that your only option? Or could it be that you never learned how to properly tuck in your shirt?

In this post, I share 5 tips for keeping your shirt tucked in neatly.

Big thanks to KK & Jay for sponsoring this article. KK & Jay makes high-quality shirttail garters and suspenders for men. All of their products are handmade in Brooklyn, right here in the USA. Use promo code TDM45 (expires 4/18/17) to get a special discount for Distilled Man readers!

1. Wear Shirt Stays

Shirt stays are the best tool for keeping your shirt tucked in neatly all day…so you don’t have to think about it.

Also called “shirttail garters,” shirt stays look a bit like suspenders. But instead of holding up your pants, they hold down your shirttails…while holding up your socks.

The big advantage is, not only do they keep your shirt tucked in, but the tension helps keep your shirt flat against your body, for a more tailored look.

If you haven’t seen shirttail garters before, they may look a little foreign to you. Surprisingly, they are not some new-fangled, trendy fad. Military professionals and law enforcement officers have been using shirt stays for years to keep their uniforms looking pristine—because they’re ideal for keeping your outfit together even when you’re active.

I’m actually glad to see shirttail garters becoming more mainstream. And it makes sense:

If I’m spending money and time to look my best, why should I allow my outfit to get messed up because my shirt won’t stay tucked in? And if there’s a low-profile accessory I can wear under my clothes to keep that from happening, why not do it?

My Experience With KK & Jay Shirttail Garters

I had a chance to try out some shirttail garters from a company called KK & Jay. They’re based in Brooklyn, and all of their products are handmade in the USA.

When you first put them on, shirttail garters feel a little different. I’ve never had something pulling down on my shirt like that. But after a few minutes, I forgot I was wearing them.

I was able to move around freely—reach up, bend over, sit down, stand up—and my shirt stayed tucked in neatly. They fit very well, even though I’m 6’ 5”.

And they were actually comfortable. It’s obvious that  KK & Jay has spent a lot of time thinking about the design of their shirttail garters, with little touches like the “Stay Tucked Leather Stabilizer” that helps the garters from turning or twisting on your legs, and the cotton blend elastics, which are soft on the skin (and come in a bunch of different colors and patterns).

Yes, but do I really NEED shirttail garters?

You tell me. Put on your favorite dress shirt and slacks, then try to go for a full day without having to readjust your shirt—especially if you’re moving around or traveling. Chances are your shirt needs some help.

Ok, but is this a luxury item?

KK & Jay’s shirttail garters are surprisingly affordable. Somewhere between a round of drinks and what you might spend on a reasonably priced tie, the cost is nothing when you consider the extra confidence of knowing your shirt is going to stay tucked neatly throughout the day.

What if I have an “overnight guest,” and they see my shirt stays when I get undressed?

Here’s the thing: if that’s the straw that breaks the camel’s back, then maybe that relationship was not meant to be. I’m just saying…

More likely is that your companion will be titillated by your “secret style accessory” and become even more attracted to your air of mysterious intrigue. After all, there’s no greater aphrodisiac than a man who’s confident enough to take good care of himself.

2. Avoid Shirts with Excess Fabric Around the Waist

One of the biggest causes of sloppy tucking is when shirts have too much extra fabric around the mid-section.

No matter how good your tucking technique, if you’re wearing a shirt that looks like it could double as a sail in the America’s Cup, you’re fighting a losing battle.

Since I’m a little lanky, most off-the-rack shirts don’t fit me. For years, I wore dress shirts that made me look like I was carrying an extra 10 pounds. Then one day while buying a dress shirt at Nordstrom, I decided to splurge for an extra $15 to have the shirt taken in.

That quickly became my favorite dress shirt, because it actually fit my body. Suddenly my muffin top was all but eliminated, and my shirt tucked in more neatly.

If you find that you have a lot of extra fabric around your belly, consider taking some of your shirts to the tailor or investing in made-to-measure shirts that are designed to your dimensions. It makes tucking much easier!

You may still need to do the usual mid-day adjustment, but it gives you a much better starting point for getting a firm tuck.

3. Use the Military Tuck

Of course, tailoring isn’t the answer for everyone. And sometimes you’ve just got to work with what you’ve got. I get it.

That’s where the military tuck comes in.

As the name implies, this technique has been used by the armed forces for years to give their dress uniforms the appearance of a good fit…without sewing a single stitch or spending an extra penny.

• Tuck in your shirt like you normally would.
• Then, gather the extra fabric around your waist and pull it towards your sides.
• Pinch the extra fabric between your thumb and forefinger, and fold the extra fabric back along the seam.
• Finally, smooth out the folds so they’re hidden…at least from the front.

While the military tuck isn’t as clean as a tailoring job, it can work in a pinch (see what I did there?).

Mainly, it does a good job of smoothing out the front of your shirt, and hiding the fabric either under your coat, or making it less noticeable because it follows the seams of your shirt under your arms. And it’s marginally better than just bunching up everything in the back like you’ve just given up.

4. Try the Underwear Tuck

If you don’t wear undershirts (or underwear, I suppose…), this won’t work. But if you’re an undergarment man, this could be a good option.

Occasionally, there’s some hullabaloo and tomfoolery that happens when your dress shirt and your undershirt spend too much time together.

Like two misbehaving classmates stuck in detention without any other stimulus, they start jostling each other and fidgeting. It’s an annoying power struggle, and in the end your billowing waistline becomes the casualty.

The answer? Keep those troublemakers separated….using your underwear.

By tucking your undershirt into your underwear, and keeping your shirt tucked in outside of your underwear, you can get a stronger, neater tuck.

I don’t know who first figured out this trick, but it can work like magic. Maybe it’s because your shirt is held down more tightly when it’s the only thing being sandwiched between your pants and your underwear—rather than competing with your undershirt in the same space.

5. Ensure Your Shirts Are Long Enough to Stay Tucked in

The final way to ensure a proper tuck is to make sure your shirts are long enough.

Have you noticed how casual sport shirts often come untucked more easily? That’s because they’re typically shorter, since many guys wear them untucked. There’s just not enough fabric to keep the shirt tucked in throughout the day.

With a proper dress shirt, you shouldn’t have that problem. True, if you choose to wear your dress shirt untucked (a no no), it will look like you’re wearing a dress…

But that extra length is a good thing when it comes to keeping your shirt tucked in neatly.

Having longer shirttails means there’s more fabric hanging below your belt line—which means there’s more surface area to grip between your pants and your underwear. Which, theoretically, means a firmer tuck.

Side note: you should also look at the length of your undershirt. If it’s much shorter than your dress shirt, the bottom edge can sometimes ride up and start to create bunching under your dress shirt (also see #4 above). That’s why the best undershirts are longer, and why you should never substitute a t-shirt for a proper undershirt.

How Will You Tuck?

If you struggle with shirts that don’t stay tucked in, don’t give up. Don’t give in to your muffin top…even it seems like it’s ruling your life right now.

You definitely have options: make sure your shirt is the right size and shape, try out the military tuck, maybe even try the underwear tuck…

But if you’re really serious about keeping your shirt tucked in neatly all day, go grab some KK & Jay Shirttail Garters. Be sure to use promo code TDM45 (expires 4/18/17) to get a special discount for Distilled Man readers.

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