The Guide to Wearing Plaid This Winter

Plaid. It’s strange to think that one little syllable contains so many sartorial possibilities. That checkered, multi-color pattern typically made from wool or twilled cloth might seem like a novelty to some. But for others, it’s a way of life.

Plaid is one of those patterns that has the luxury of functioning both as a trendy fad and as a vintage classic—no one can quite tell the difference. But the good news is, if you plan on investing in a few plaid items for your wardrobe this winter, you’re likely going to see years of use out of them and still feel properly dressed and never out of style. Particularly when fall and winter inevitably roll around again.

There’s just one problem: you’ve never worn plaid and you’re not sure how to start. Well, you’ve come to the right place.

Start with Subtle Hints of Plaid

You don’t have to go full Al Borland just yet. If you’re interested in adding plaid to your wardrobe, start by wearing a shirt that doesn’t feature too many unusual colors. This Dip Dye Vintage Plaid Khaki shirt, for example, features a bold pattern…but it’s not so overwhelming or unorthodox that it will call special attention to yourself.

If you want to keep the plaid subtle for now, focus on a few key tips:

• Use plaid as a base layer and add something more neutral on top of it—even if it’s as simple as a gray sweatshirt. It’s winter, after all: you’re going to want to layer anyway, so you might as well start tossing plaid into the mix.
• Try an accessory or two. Plaid scarves are all the rage; they provide a pop of wholesome color to an otherwise monotone wardrobe. If you tend to dress in all blacks, blues, and greys during the winter, a simple buffalo plaid scarf will be enough to make your style draw the eye—in a good way.

Featuring Plaid in Your Winter Wardrobe

Let’s say that, like Al Borland, you’re as comfortable with plaid as you are in your own skin. Great! You’re ready to start featuring items like this Yarn Dyed Plaids Maize shirt—incorporating both bold patterns and bold colors into your regular routine.

How do you pull it off without ever clashing? After all, a plaid shirt always brings multiple colors to an outfit. The answer is simple: ground it. Keep your other items monochromatic. A pair of Military Twill Classic Fit in British Tan pants will provide a nice, neutral counterpoint to the pops of color you have going on elsewhere in your outfit.

Since it’s winter, don’t forget to layer with a similarly neutral peacoat (black, charcoal, tan—you can’t go wrong with something neutral) and your plaid will still pop without overwhelming the entire outfit. And as a side benefit, all of this layering helps keep you warm even on winter’s chilliest days. Maybe Al Borland was on to something after all.