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How to Wear Plaid: 5 Men’s Outfits for Fall

We’ll be wearing this classic print every chance we get.

Variety of men’s plaid shirts
September 5, 2019

Plaid is synonymous with men's fall fashion, and for good reason, too. This multi-colored motif was a popular ‘90s trend but it’s so versatile we still consider it an essential for every wardrobe—regardless of personal style. Check out our style guide for five different plaid outfits and easy tips for how to achieve each look.

Keep it classic

This is one of our favorite ways to wear a plaid shirt because it’s just as practical as a T-shirt and jeans, only more interesting to look at. Using only wardrobe staples to put it together, we’re keeping this outfit simple without compromising on an ounce of style.

  1. Start with your favorite pair of jeans. A pair of black or dark-washed denim with a slim-fit gives a bit of edge without feeling too grungy.
  2. Add a denim jacket. To create an easy-going layered look, make sure your jacket hits at the waist so that your shirt tails are still visible.
  3. Bring everything together with a simple pair of black-and-white sneakers and your favorite pair of sunglasses.

Take it outdoors

Fall weather can fluctuate between warm and cool throughout any given day, so it’s important to consider the temps when getting dressed. For plans that include a visit to the pumpkin patch or a drive with the top down, having the right outerwear will keep you comfortable.

  1. Layer on the warmth with a slim-fit cotton vest. The sleeveless design is non-restricting and gives your outfit some rugged appeal
  2. Choose light-wash jeans to prevent the look from feeling too heavy, then give the hems a slight roll for a smart touch.
  3. Finish by picking a pair of chukka boots that match your outerwear, keeping both pieces within the same color family.
Men’s plaid outfit with vest

Go ahead and relax

For days when comfort is a priority, this athleisure-inspired outfit will become your new go-to. It’s casual and cool with just the right amount of chill.

  1. Take your softest graphic tee and style it with a pair of neutral colored jogger pants.
  2. Keep with the low-key vibe of the day by wearing a baseball hat, instead of styling your hair.
  3. For warmer afternoons, tie your plaid shirt around your waist and cuff the sleeves of your T-shirt. 

Dress it up

Since plaid shirts are typically considered casual, dressing it up can seem a bit challenging. But the truth is, it’s easy to do and can be worn for work or a dinner date. It all just depends on what you style it with.

  1. Begin by tucking your shirt into a pair of richly colored chino pants.
  2. Highlight the subdued shades within the plaid print with a wool blend sport coat in a coordinating shade.
  3. Round out the look with shoes that walk the line between casual and formal, like a classic pair of suede loafers.
Men’s dressed-up plaid outfit

Add a handsome touch

From dressed up to dressed down, we’ve shown you how to style plaid shirts several different ways. So for this last look, we’re going for something in between. This smart casual outfit is both polished and neat, making it ideal for a variety of occasions.

  1. Go for khakis. They’re a tried-and-tested favorite that will hardly ever steer you wrong. Plus, they’re great for pairing with plaid.
  2. Gauge whether or not you want to tuck in your shirt based on where you’re headed and the level of formality required.
  3. Tie the look together with sturdy lace-up shoes that balance both style and practicality. 

Now that we’ve made the case for why plaid is a must-have in any man’s wardrobe, make sure to talk to a stylist about trying the print for yourself.