Spoiler alert: shirts can be left untucked. Some are designed to hang free, while others just look better that way. Your dad may not have received the memo, but since when did you start listening to anything he said?
If you’re the kind of guy that likes a little fabric around his tooshie, then the best untucked shirts should be firmly on your radar. But with so many options readily available, where do you go to find the crème de la crème? I’m glad you asked.
Keep reading for my lowdown on the finest shirts money can buy. You’ll find a plethora of designs from brands you love, plus plenty of tips on how to wear them.
Key Takeaways
Tucking or untucking different types of shirts can really set the tone for your outfit. Especially when it comes to formality.
For the sake of this guide, I’m going to be focusing on the shirts that should be left to hang freely on the outside of your pants. From L’Estrange’s button-down Oxford to
If the best untucked shirts of this world were to line up in an arena and battle it out like gladiators, there’s only one style guaranteed to triumph. The button-down Oxford is the ultimate smart-casual staple; looking just as good with khakis and loafers as it does with jeans and boots.
This version from
Material: 98% Organic Cotton, 2% Elastane | Colors: 3 | Sizes: XS-2XL | Care: Machine Wash
A tucked-in shirt can make you feel restricted. Leaving you afraid to move in fear of fabric escaping and leaving you a little uncouth. Which is why the best untucked shirts are the ideal option for day-to-day wear.
Luca Faloni’s is smart enough to wear with slacks while fitting in perfectly with dark jeans or slim-fitting khakis. It’s crafted from luxurious Egyptian cotton that’s known for its hypoallergenic qualities and unrivaled breathability. So even on warm days, you’ll still look your best.
Material: 100% Cotton | Colors: 4 | Sizes: XS-4XL | Care: Machine Wash
Some shirts are better suited to particular times of the year. For example, your favorite Hawaiian number should be saved until summer. Others, however, are transeasonal. Looking just as good in the depths of winter as they do during the heights of spring.
The denim shirt offers such versatility. And my go-to is this one from
Material: 100% Cotton | Colors: 2 | Sizes: XS-XL | Care: Machine Wash
Once upon a time, untucked shirts were the kind worn by unruly schoolboys who walked the halls with ties too short and sneakers disguised as shoes. Today, they are a must-have in every well-rounded wardrobe. Which is why Amazon offers them aplenty.
My favorite (and soon to be yours) is this one from UNTUCKit. Specifically designed to be left outside of your pants, it’s an excellent all-rounder that can be paired with jeans, khakis, or slacks. It’s made from nylon with plenty of stretch to ensure all-day comfort and optimum mobility. If you like what you see, bear in mind that the cut of this style is slightly smaller than many other brands. So, if you are between sizes, I suggest ordering one size up.
Material: 92% Nylon, 8% Elastane | Colors: 1 | Sizes: M-XL | Care: Machine Wash
When it comes to dressing smartly, your default outfit is probably going to be a shirt and tie. And if this is the case, you should always be tucking yourself in. But what if I told you that you can still look the part, yet feel considerably more comfortable?
COOFANDY’s muscle fit option looks best untucked. Better yet, it hugs you in all the right places, yet has plenty of stretch to keep you comfortable throughout the day. Wear it with slacks if you’re dressing up, otherwise it’ll look great with a pair of skinny jeans.
Material: 50% Cotton, 48% Polyester, 2% Spandex | Colors: 24 | Sizes: XS-4XL | Care: Machine Wash
Remember when I said your dad didn’t get the memo about untucked shirts? Well, he probably didn’t. But I’m confident he’ll know about the power of a good corduroy number. So why don’t you make him proud with a wallet-friendly option from H&M?
Comfortable yet handsomely rugged, it’s the kind of shirt you’ll turn to season after season—and chances are it’ll only look better with age. I’ll often wear mine open with my best T-shirt and jeans, but it can look just as good buttoned up with cargos and your favorite high-top sneakers.
Material: 100% Cotton | Colors: 4 | Sizes: XS-3XL | Care: Machine Wash
Luxury isn’t necessarily determined by the brand name. And the best untucked shirts aren’t always the most expensive. Yet this Fear of God design proves that sometimes this is the case. So, pull together the funds and make an investment you certainly won’t regret.
Featuring dropped shoulder seams for a relaxed, contemporary look, it’s a must-have for streetwear enthusiasts and city dwellers alike. You can wear it with dad jeans and sneakers for a slightly casual ensemble, or dress it up with slim-fitting slacks and Derby shoes. Either way, you’ll be the talk of the town.
Material: 52% Cotton, 46% Wool, 2% Elastane | Colors: 3 | Sizes: XS-3XL | Care: Dry Clean
A work shirt should be smart but you also need to be comfortable wearing it. There’s nothing worse than spending the day wishing you could rip open the buttons and slip into your favorite cheap tee.
Non-iron styles are great for convenience. Problem is, they often come with a longer hem—meaning they look a little messy if you leave them untucked. The solution is Savile Row Company’s blue twill shirt. Cut shorter in the body, you can let it hang free as you pair it with everything from khakis to smart slacks.
Material: 100% Cotton | Colors: 4 | Sizes: S-XL | Care: Machine Wash
On days when flannel shirts feel a little too stuffy, a timeless Henley tee is your happy medium. They may not get you through the door of an ultra fancy restaurant, but they’re an awesome everyday choice that offers endless styling opportunities.
This one from Schiesser can be worn alone with shorts and espadrilles, or layered underneath an overshirt with cargos and sneakers. The ribbed neckline and cuffs give it a slightly more serious feel, but for relaxed days in the city, you could simply roll them up and leave a few buttons undone.
Material: 100% Cotton | Colors: 1 | Sizes: S-2XL | Care: Machine Wash
Untucked men’s shirts are great for everyone. But when it comes to guys measuring below average height, it’s important to pick a style that isn’t going to make you look smaller. So how do you do that? It’s all in the fit.
Cut to a slim shape to ensure you’re not swamped by fabric, Onia’s smart-casual staple hits all the right notes. Presented in navy for ultimate versatility, it should fall just above your pants fly—giving off the impression your legs are long and your torso is just right. Wear yours with shorts in the summer, swapping them for jeans or khakis as the temperature turns.
Material: 52% Linen, 23% Cotton, 23% Rayon, 2% Spandex | Colors: 3 | Sizes: S-2XL | Care: Hand Wash
What To Look For In The Best Untucked Shirts
Style
Not all shirts can be left untucked. So if you’re planning to wear it that way, it’s important to make sure you’re buying the right one.
Unless it’s specifically a longline design, those with a longer hem (below your pants fly) are designed to be tucked in. So are dress shirts. If it’s shorter, you can leave it untucked.
Color
Choosing the color of your shirt is not only a matter of personal preference. You should also consider when and where you plan to wear it. For ultimate versatility, stick to classic colors such as white or blue.
Bold patterns and bright colors may be your cup of tea (and they’re great), but just bear in mind that this could reduce the number of times you get to show it off.
Material
The material of a garment doesn’t just have a say on its comfort, but also how easy it is to care for. Certain fabrics are also better suited to different types of weather. Cotton is an excellent all-rounder, while linen should be saved for the summer. Don’t be afraid to do a little more research to make sure you’re making the right purchase.
Final Verdict
Your search for the best untucked shirts should now be nearing its conclusion. Simply take your pick from my recommendations and you’ll soon be gloating as the compliments fire your way.
And if you’re still weighing up your options, don’t forget about L’Estrange’s button-down Oxford. A timeless addition to any wardrobe, it’s the perfect versatile piece that’ll easily slot itself into your current everyday rotation.
FAQ
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Generally speaking, casual shirts, such as the button-down Oxford, look the best untucked. However, you’ll also come across certain formal styles that do too. The key is in the length of the hem. If it’s too long, tuck it in. If not, you can leave it untucked.
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To determine whether or not your shirt can be left untucked, simply check where it falls on your lower body. Shirts that sit around the fly on your pants can be left untucked. If they’re any longer, you’ll probably need to tuck them in.
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For the most formal settings, an untucked shirt may be considered unprofessional. Especially if you’re wearing it with a tie. However, for weekend fits or business casual attire, it’s perfectly acceptable.
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