By Alicia Harper

When looking your best, comfort equals confidence. But looking sharp and being comfortable aren’t mutually exclusive. Simply untucking your collared shirt gives a quiet reassurance that you know how to look great—and break style rules. Although, wearing a shirt designed to be untucked is key.

If you haven’t tried pushing the boundaries with untucked shirts designed for comfort, not conformity, now is the time. The good news: You can pull off untucked looks at more formal occasions than you ever knew. Whether you’re hoping to land your next gig or a second date, here are five typically tucked occasions where you can forgo the tailor and opt for an a casual, yet polished shirt you can wear untucked.

 

Job Interviews

 

When trying to land a new job, being overdressed can be just as bad as underdressed. Luckily, the dress code at many offices is leaning away from buttoned up and more relaxed, depending on your industry, and suits are no longer a requirement. No matter where you’re interviewing, you can never go wrong with a crisp solid-colored button-down. With the right length, going untucked can look even more polished than tucking in your shirt. Add some personality to your look with a plaid or windowpane sport coat made from soft wool—great for colder months, and save your fancy silk ties for another time (as in never).

 

Destination Weddings

 

Before you call BS, just hear us out. Destination weddings are more popular than ever, and send a clear message to its attendees: “We’re here to have a good time, so loosen up!” And they’re talking about your clothing. If the nuptials are in a tropical locations, you have the green light to go untucked.

For a smart, breezy way to ward of the heat and show some character, wear a gingham or checked short-sleeve shirt. Pair it with some lightweight cotton twill pants in a fun color for the perfect combination of laid back and dressed up. You can bet that the guy to your left in the stuffy suit and tie will be jealous of how comfortable you look.

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A First Date

 

First impressions matter—a lot. Whether you like it or not, your date may make a snap judgement based on your clothes before you get a chance to open your mouth.

The goal? Look put-together, yet casually cool as possible. So instead of a solid, tucked-in (read: predictable) shirt, opt for a more memorable flannel or colorful, plaid button-down and let your shirttail fly free. Then add a pair of slip-on sneakers to match your relaxed vibe. We can’t promise the date will go perfectly, but we can promise you’ll look good the whole time.

 

Cocktail Parties

 

We’ve all been there—standing in front of your closet wondering what to wear to the party you RSVP’d to. Here’s a hint: Don’t reinvent the wheel every time you get dressed. A shirt-and-sweater combo is always appropriate for fall. Which shirt and sweater you wear is the key. Start with a wrinkle-free button-down that will always look crisp and show fellow party-goers that you cared enough to iron. (No one has to know you didn’t.) Throw on a navy washable merino wool sweater on top so you won’t have to spend extra cash on dry cleaning, and suddenly, you’re the best-dressed guy in the room.

 

Your Big Presentation

 

When your big moment arises and all eyes are on you, reach for comfortable, reliable styles that let you focus on your work—not your shirttail. The formula is simple.

Throw on a smart, performance button-down that’s treated to repel moisture before it causes embarrassing pit stains. Even better, choose a style with built-in stretch so you move confidently around the boardroom. And if the office AC is cranking, layer up in a soft wool sweater with a zippable placket. Because when you look smart, you’ll feel smart too.