The New WorkKit

How to Wear Plaid for Any Occasion

by Faran Krentcil

If you’re wondering how to wear plaid, then you’ve got great timing. Winter is the perfect season to test-drive plaid in new and unexpected ways because the favored fashion pattern is often made with seasonal fabrics like flannel or wool. Plus, thanks to its graphic possibilities, plaid looks great as part of a layered ensemble, too.

Here are our favorite ways to wear plaid for every occasion.

Plaid Outerwear

Plaid Trench

‘Tis the season for the all too familiar winter fashion dilemma: cold, gray days when you need to look sharp, but just want to pile on a giant snuggly sweater and call it a day. Fortunately, the right coat can make you look far more capable than you feel, especially if it has a structured shape and a dynamic, textured pattern.

Enter the plaid topper coat. It’s a great choice because of its streamlined silhouette, its geometric pattern, and its chic length, which hits just below the knee. Cinch its wool belt across your waist and you’ll have a tied-together (pun intended), effortlessly chic outfit.

Plaid on Date Night

Wearing plaid on a date doesn’t mean you’re limited to Britney-esque, Catholic schoolgirl-inspired kilts. Instead, try a fitted A-line dress in a plaid print, with a subtle V-neck and nipped waist. You can pair it with a moto jacket for a ’90s throwback, or with a feminine solid-colored bow belt and strappy pumps for a more romantic riff. And if the date’s a dud, hit the dance floor with your girlfriends instead.

Plaid on the Bottom

comfort stretch pants

Did you know that you can elevate any look with one quick switch? Here’s how: keep your skinny jeans in the drawer, and swap them out for a pair of slim plaid pants. Worn with a blazer and kitten heels, they’ll complete a perfect office ensemble. And when paired with your favorite crewneck sweatshirt and loafers or sneakers, plaid pants can even complete a super cute look you can head to brunch in.

Plaid on Top


But what if you’re the type of person who can’t bear to part with your favorite pair of leggings or jeans? Don’t worry, there’s a pretty easy strategy for how to wear plaid, while still staying loyal to the almighty denim and athleisure trends.

When worn buttoned over a turtleneck or even a T-shirt, a plaid trophy blazer can be paired with a pair of beloved denim or leggings. The strong shape and bold pattern of the jacket convey purpose and style, while more casual pants give off a hip vibe that rounds the look out.

Plaid Work Vibes

Sometimes the best office outfit has nothing to do with runway or red carpet trends. When you want to invest in an option that’s always chic and smart, a pencil skirt is a tried-and-true winner. Getting one in plaid adds a great visual pop to your workwear, and it’s an item that plays very well with others. You can pair it with a crisp white shirt, an oversized sweater, a cropped leather jacket, a bright blouse, or a matching blazer for a timeless look.

Are you feeling mad for plaid yet? Whether you’re off to the office or a winter weekend getaway, knowing how to wear plaid in a stylish, thoughtful way can take your wardrobe to the next level.

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