The Kiki sweater, Mila shirt, and Milo jeans.
How to Tuck in a Shirt (Five Ways)
When done right, this often-overlooked styling technique can truly transform an outfit.
If I could reclaim every minute I’ve spent standing in front of my mirror aggravatedly tucking, untucking, and re-tucking shirts, wondering why my outfit doesn’t look “right,” I could probably watch a Hallmark movie every day now until Christmas. The perfectly styled outfits you see on social media might make you think that everyone but you knows some secret trick to looking chic without trying, but the truth is, we’re all trying. And a lot of developing your confidence and personal style comes from trial, error, and, sometimes, having a meltdown in your closet three minutes before you’re supposed to leave your house. We’ve all been there.
Despite the fact that I give styling advice for a living, I still experience that I-hate-all-my-clothes feeling from time to time. But over the years, I have learned a few things that help. The biggest lesson? I don’t actually hate my clothes; I just need to find new ways to style them.
So today, I wanted to share an often-overlooked styling technique that, when done right, can truly transform an outfit: the tuck. It sounds cliché, but I’m not exaggerating when I say that a good tuck can turn a sloppy outfit chic in seconds. Below, I’ve compiled the best shirt-tucking tricks I’ve picked up over the years—both from the styling experts I work with and from those aforementioned hours of frustration in front of the mirror—plus outfit ideas to try.
Want more M Dash?
Sign up for our weekly newsletter.
Thank you!
How To Tuck in a Shirt (Five Ways)
1. The Oversized Shirt
Employing a half-tuck is an easy way to give oversized button-up shirts, such as the Mila, a more polished vibe. To achieve the look, leave the last couple buttons of the shirt undone, then tuck the flap with the buttons into your pants or skirt. Once you’ve secured the tuck, pull the tucked half out ever so slightly to add a bit of volume.
2. The Fitted Shirt
For fitted shirts, it’s best to stick with a full tuck. To prevent lumps and bumps from excess fabric, tuck your shirt in smoothly before buttoning up your pants or skirt. Once you have a good tuck, try raising your arms above your head to make sure your outfit offers full mobility, and that you can trust your shirt to stay tucked throughout the day.
3. The T-Shirt
With the right styling, a tucked-in T-shirt can seamlessly stand in for more formal underpinnings—perfect for a Power Casual office look. I like to start the tucking process by pulling the fabric down until it’s taut to make sure the shirt stays put, then lightly pulling it out to create some slouchiness. For a relatively tailored tee like the Leslie, I’d aim for just a small amount of slouch; but for ultra-oversized tees, you can embrace the look by leaning into the slouchiness more heavily.
4. The Sweater
While sweaters like the Kiki don’t need to be tucked in to look polished, incorporating a French tuck (or front-tuck) is an easy way to give your outfit a more styled look. For sweaters, I recommend beginning the tuck after you’ve zipped up your pants. The key to making this work is selecting the right rise pants for your proportions and your sweater. As a rule of thumb, your sweater should fall at least two inches below your pants’ waistband in order to stay in place.
5. The Long Shirt
The key to successfully tucking in a long shirt is to choose bottoms with enough room to accommodate the extra fabric (bonus points if they have an elastic waistband). Make sure to smooth the fabric out fully, paying special attention to the sides of the shirt, which may want to ride up depending on your proportions.
Tucked-in Shirt Outfits
Outfit #1
The Oversized Shirt
A half-tucked poplin shirt is preppy in the best way—and a shortcut to looking stylish without going wild with accessories. I love pairing oversized button-downs with high-rise, wide-leg jeans for some fun proportion play. Make the look winter-ready by draping a bright-red chunky sweater over your shoulders.
The Mila shirt and Milo jeans.
The Kiki sweater, Mila shirt, and Milo jeans.
The Axam turtleneck and Milo jeans.
The Jolie jardigan, Axam turtleneck, and Milo jeans.
Outfit #2
The Fitted Shirt
When it’s cold outside, there’s no better way to stay cozy than by tucking in the fitted pima-cotton Axam turtleneck. While you could technically leave this shirt untucked, tucking it in will ultimately keep you warmer—and make it easier to layer. Here, I’ve added the Milo jeans in fawn for a chic, monochromatic look in a palette that may or may not be inspired by my dog. The stretchy Jolie jardigan in chocolate completes the comfortable office-ready ensemble. Want to try a similar look for more formal events or offices? Just replace the jeans with the wide-leg Horton pants and the boots with pumps.
Outfit #3
The T-Shirt
Tucking in a shirt when wearing jeans is a good way to give your outfit a bit of extra polish. And this look proves that you can transform comfortable, casual work clothes for formal occasions in two simple steps: First, tuck your trusty Leslie T-shirt into your favorite Better Than Denim jeans; and second, add festive accessories like heeled booties and a head-turning jacquard jacket (because who wants to wear dress shirts when you can get away with a tee and look just as fabulous?).
The Leslie T-shirt and Hockley jeans.
The Nicky jacket, Leslie T-shirt, and Hockley jeans.
The Kiki sweater and Milo jeans.
Outfit #4
The Sweater
The great thing about the gorgeous Kiki sweater is it does the styling for you. Between the bold color, the elegant cable stitching, and the ever-so-slightly boxy silhouette, you don’t need additional styling to look great. Just throw it on with your Milo jeans and, should you feel so inspired, try a front tuck. If you want to give your outfit a bit more structure, you can wear a belt.
Outfit #5
The Long Shirt
I love wearing my sleek Giulia top untucked over fitted pants like the Foster, but when I pair it with roomier silhouettes like the Shane, tucking is the way to go. Here, I’ve styled the basil-green Giulia top with the Shane pants in navy for a playful palette that works any time of year. During the winter months, add a cozy cashmere quarter-zip to create an outfit that’s simultaneously casual and luxurious. (P.S. For those who haven’t tried the Giulia, this is the type of shirt that you have to try on to really “get” how amazing it is. Just trust me.)
The Giulia top and Shane pants.
The Cece sweater, Giulia top, and Shane pants.
The Cece sweater, Giulia top, and Shane pants.
