The ultimate guide to timeless plaid shirt styling

Timeless plaid shirt looks you’ll wear for years — styling hacks
Woman in a plaid shirt. Photo: freepik

In the fall, a plaid shirt is more than just a basic item. It can be the focal point of your outfit or provide a subtle backdrop for other pieces. It looks very cool when paired with a sweater. This combination is comfortable, stylish, and allows for experimentation.

Discover versatile plaid shirt outfits that stay stylish season after season, according to Cosmopolitan.

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Plaid shirt outfit ideas that never age

Stylists suggest wearing a sweater over a shirt, leaving the collar and bottom slightly visible. This layered effect adds texture to the outfit. Jeans, Palazzo pants, or classic suit trousers will complete the outfit. The look can also be complimented by the shoes of different styles: loafers add a light academic charm, high boots add elegance, and sneakers add ease.

5 Plaid Shirt Outfits You’ll Repeat Every Fall
A cozy look. Photo from Instagram

To make the look less boring, you can add with details:

  • tuck your shirt halfway under your sweater;
  • tie it on the belt over the sweater;
  • add a belt and throw the sweater over your shoulders for a slight "untidy elegance";
  • Wear a sweater in bulk and tuck in only the front of the shirt to create a casual chic effect.
5 Plaid Shirt Outfits You’ll Repeat Every Fall
Shirt with a belt. Photo from Instagram

This season, different types of plaid are trending: tartan, Prince of Wales, and glen plaid. Tartan exudes a classic British vibe, glen check has a subdued and professional look, and Prince of Wales is perfect for pairing with coats and trench coats.

5 Plaid Shirt Outfits You’ll Repeat Every Fall
Stylish look with a plaid shirt. Photo from Instagram

To create a more creative outfit, try combining a shirt, a sweater, baggy jeans, and loafers. Another option is to wear a shirt with suit pants, a bomber jacket, and ballet flats. For a feminine look, try a miniskirt with a plaid shirt and a coat. High boots will perfectly complement this look and help create a modern, sophisticated style.

5 Plaid Shirt Outfits You’ll Repeat Every Fall
Trendy shirt print. Photo from Instagram

A plaid shirt under a sweater is not only comfortable; it's also a way to experiment with textures, layers, and proportions to give classic items a modern, unique look. It will definitely be your must-have in the fall of 2025.

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