There are likely a lot of decisions on your mind when Valentine’s Day is on the horizon. What should I wear to my Valentine’s dinner? What gift should I give to my significant other? Did I remember to make that dinner reservation six months ago? Don’t overthink it: UNTUCKit has the answers to all your questions—well, most of them at least. 

Your look should be relaxed without being sloppy, polished without putting on airs, and comfortable without being loose. That’s where we come in. Our untucked shirts, sweaters, polos, and more offer the ultimate combination of sharp and casual. And with so many ways to wear them, you can outfit to match your vibe without being boxed into the traditional rules of dressing. 

We know for a lot of people, Valentine’s Day is just a Hallmark holiday. But it has as much meaning as you give it—and for some of us, that’s a lot. So if you’re looking for fresh styles to liven up your Valentine’s look, or if you’re searching for the perfect present to say “I love you,” take a look below for some inspiration. 

 1. Wrinkle-Free Douro Shirt



Want to gift him something he’ll love to wear again and again? Nothing says “Valentine’s Day” like a colorful pop of pink to liven up his closet. The subtly eye-catching Douro shirt has a soft, rose-tinted fabric that looks great this time of year, and also effortlessly transitions into spring’s pastel palette. Of course, it also features our amazing Wrinkle-Free treatment so he won’t have to fuss with the iron or dry cleaners—which is a pretty nice gift in itself. 

One of our Iconic Button-Downs, this untucked dress shirt is an oldie but a goldie. It looks almost solid pink at a distance, but reveals thin vertical white stripes that give it extra depth up close. Under a sharp sport coat or cozy sweater, this style provides a lively burst of color that’s sure to bring the Valentine’s vibes wherever you’re headed. Wear it with a pair of our 5-Pocket Chino Pants for a look that’s both refined and relaxed.

2. Wrinkle-Free Performance Peraldi Shirt


Just like the journey to finding your one-and-only, your busy schedule can be unpredictable. Don’t sweat it—the Peraldi is here for your morning commute and your evening plans alike. Maybe it’s your first Valentine’s together and you’re, understandably, a little nervous. Maybe you don’t have time to change between work and your date. Maybe you just love the way this style looks. Whatever the reason, the untucked shirt’s crease-fighting, sweat-wicking technology will get you wherever you need to be looking as fresh as when you first put it on. 

At a distance, this shirt looks practically solid, but upon closer inspection reveals a cool red and navy microprint that’s sure to catch her eye on your special day. Dress it up with an Italian sport coat and a pair of our Classic Chino pants to make a dapper entrance that would make even Aphrodite blush.

3. Wrinkle-Free Clark Shirt


Whether you’re looking for something to wear to your romantic evening together, or you’re browsing for a great gift to give your special guy, this Wrinkle-Free style is a great starting point. Under a sport coat or on its own, the Clark shirt is a year-round staple that looks great on every guy. It fights creases all day long for an always-fresh look, making it an easy go-to when you need to dress sharp in a flash. 

This no-tuck shirt’s midsize windowpane check pattern easily dresses up or down, making this one of the most versatile styles you can wear this season and beyond. Even though it works all year, its subtle yet vibrant rose color gives it a look that’s perfect for Valentine’s Day. 

4. Heavyweight Polo


If your guy is big on no-tuck polos, get him this heavyweight winter-weather shirt that he can enjoy now through spring. Its extra-thick fabric is bulky enough to block a breeze, but thin enough for easy layering under a water-repellent jacket. Somewhere between a regular polo and a sweatshirt, this in-between style is great for those cuddle-up-inside afternoons—you might even need to borrow it when he’s not looking. 

Unlike traditional polos, its long sleeves are perfectly suited for colder days. It has a vibrant red hue and a cool mottled texture that gives it additional depth compared to ordinary solid polos. Plus, its stretch collar and easy-roll sleeves give it a relaxed feel that he won’t want to take off. Gift it with a pair of our incredible Traveler Tech Pants for his easy Valentine’s Day present. 

5. Button-Neck Donegal Sweater


As much as Valentine’s Day is about warmth, don’t forget that it technically falls in the middle of winter. This unbelievably soft sweater turns up the heat—and the texture—for a look that works over any untucked button-down. Its lambswool blend fabric is essential for staying at just the right temperature without overheating. Plus, its easy button-neck allows for even greater adjustability.  

When it comes to your special day together, you’ll want to wear rich shades of red. This style takes things a step further. Named for the Scottish town from which the fabric originates, this sweater has an immediately recognizable character that’s richly dyed, texturally deep, and of course, irresistibly soft. You’ll love the comfy feel and suave look when it comes time to light the candles on your big date. Layer it over a Wrinkle-Free shirt to look like a million bucks in an instant. 

6. Wrinkle-Resistant Palazzo Sport Coat


Want to elevate your Valentine’s Day look in a heartbeat? This combination of a Wrinkle-Resistant sport coat plus an untucked button-down is a match made in heaven. Made in an Italian mill from 100% breathable wool, this blazer features a fully-lined interior, two flap pockets at the waist, and a wrinkle-fighting treatment means you’ll never have to worry about those pesky creases. 

This sharp jacket in a classic black or cool gray color immediately strikes a bold, confident look. We recommend pairing it with a softer color—think lighter shades of red this holiday—which will support the jacket without overpowering it. Try it over our Wrinkle-Free Douro Shirt with a pair of Classic Chino Pants for a comfortable style that’ll look polished all night. 

7. Traveler Tech Pants


So you’ve found a great untucked shirt to make your Valentine’s Day unforgettable. But did you know we also make the perfect-fitting men’s pants to match? Out streamlined Traveler Tech Pants feature a wrinkle-resistant, water-repellent fabric with a hint of stretch so you can move comfortably and look sharp from the commute to the candlelit dinner. They’re tapered below the knee for an elevated, modern look that’ll expertly complement your untucked style. 

This time of year, it’s especially important to be prepared for unexpected weather. Don’t let a random downpour or slushy sidewalk ruin your clean look. These pants have all the benefits of our amazing Performance fabric that’ll keep you dry and looking great for your Valentine’s Day evening. 

8. For Her: Satin V-Neck Malorie Dress


We’ve talked a lot about what to get him for Valentine’s Day, but we saved the best for last. Ladies, treat yourself to a fresh take on the classic red dress: The Malorie has a vivacious color that perfectly embodies the feeling of the holiday, and its flattering silhouette is both elegant and comfortable. You’ve heard of “Pretty in Pink,” but we’re here for “Radiant in Red.” 

Featuring a convenient button-down front, a flattering midi length that falls just below the knee, and just enough stretch for easy movement, this dress is a comfortable way to turn heads this Valentine’s Day. Contrasting against the desaturated colors of wintertime, this style stands out like a rose in a snowy field.