6 Modern Ways to Wear Plaids This Fall and Winter

When it comes time to switch out summer staples and bring in fall fundamentals, we immediately turn to a timeless pattern: plaid. Sure, the checkered print can sometimes lean passé or lumberjack, but there are plenty of ways to breathe some fresh, cool air into the classic look. Whether you’re trying to make plaid the focal point of your outfit with an expertly pleated mini dress or just want to take the style out for a spin with a subtle shoe, here’s how you can style the pattern for your personal aesthetic this fall and winter. 

Ahead, discover six plaid-centric outfits featuring understated and attention-grabbing garments alike.

Pretty in Pink

If you’re the type to command attention, this tartan mini dress from Molly Goddard is for you. The print can sometimes feel overbearing, but here, the asymmetrical draping and the pleated skirt break it up, making for a more interesting appearance. Plus, who doesn’t love a bow embellishment?

Post-Grad Uniform

It’s hard not to think of some of the most famous preppy girls in television history when you see a plaid mini. From Mia Thermopolis to Rory Gilmore, all the famous fictional private-school students relied on short skirts to tie their outfits together (even if it’s because it was the mandated uniform).  Those short hemlines never really go out of style. The 2023 way to style the look? With a brown leather-look trench and heeled boots, a creamy knit and a sparkly mini bag. 

Carrie Bradshaw Core

“And Just Like That” brought us plenty of modern Carrie Bradshaw fashion but if we had to style a plaid-ified look for the queen of Manhattan ourselves, a corseted bustier with just enough colors to pull from for each accessory sounds about right.

In My Literal “Red” Era

This outfit is giving “Begin Again” vibes — only in New York, as opposed to Paris. (If you know, you know.) Plus, the combination of deep navy, red and white on this plaid skirt makes for a subdued color scheme that still maintains its statement-making abilities.

I’m With the Band

Nothing says “rock star” quite like leather and tartan. Don’t be afraid to mix fabrics, prints and textures for a chaotically considered look. Then, channel your inner punk with a gold studded accessory.

Equestrian After Hours

These plaid kitten heels from Jimmy Choo are just preppy enough to carry the preppy uniform feel without feeling childish. With an expertly tailored blazer over a mini skirt, accessorized with leather gloves, it feels like what someone would change into after an afternoon of horse riding. Complete the look with a fancy headband.

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