As our bikinis and shorts take their final bows for the season, we’ve started to plan out our ‘sweater weather’ wardrobe. Oversized knits, beanies, and a variety of boots will be in our rotation, but if you’re looking to plot your aesthetic by pattern, plaid outfits deserve a spot in your 2020 mix.

Maybe it’s because Clueless celebrated its 25th anniversary this year, and subconsciously, we enjoy paying homage to Cher Horowitz and Dionne Davenport’s checkered mini skirts and blazers. Or, it could be the fact that preppy style never really stops trending. Either way, plaid will be everywhere this fall, and thankfully, street style inspiration for how to nail this look is plentiful. 

Here are some of our favorite plaid outfit combinations that are worth trying out.

A Plaid Coat Over Sweats

Throw a tailored plaid blazer or peacoat over your sweats in order to elevate your loungewear. With this simple hack, your look will go from cozy-comfy to sleek in a matter of seconds. 

A Plaid Button-Down Over a White T-Shirt

This laid-back ensemble gives us major ‘90s vibes. The classic combo of an oversized, plaid button-down with denim and a white tee works for a variety of fall activities, and makes a statement all its own. However, if you’re really looking to bring home the decade’s sassy-grunge aesthetic, add a bold belt to your look.

A Plaid Dress

In addition to a little black shift, we highly recommend adding a plaid dress to your capsule wardrobe. Whether you’re heading back to the office or having dinner outdoors on a breezy night, it works every time, and is a great trick for incorporating prints and color in a more subtle way.

A Plaid Skirt Styled With a Graphic Tee

Plaid skirts are pretty much synonymous with ‘schoolgirl,' but if you own this classic piece, you can easily switch it up. Instead of going with something simple on top, like a button-down or sweater, try a graphic tee, which is an unexpected and eye-catching option.

A Plaid Button-Down Over a Dress

Plaid shirts have the power to transform your whole outfit, and you’d be surprised at how versatile they can be. An oversized plaid shirt styled with a sexy mini dress will make your outfit less formal, turning it into something cool, calm, and collected. 

A Plaid Blazer

Fashion lovers know that it's worth it to add a blazer to their closet  — pairing one with a blouse and a skirt or even jeans is a go-to easy outfit. However, we also love the idea of wearing this checkered essential as a deep V-neck mini dress, accessorizing with jewelry and heels.

A Plaid Top With Leather Bottoms

Offsetting cozy plaid tops with leather bottoms is a great way to combine two timeless fall trends. Tuck a gingham button down into a leather mini skirt, then accessorize with thigh-high boots, or loosely tie your top at the waistline before pulling on black leather pants. The combinations are endless depending on your style, mood, and destination.

Plaid Pants

We love our jeans and solid colored slacks, but on occasion, we’ll reach for a good old pair of plaid pants instead. While they no doubt look great when worn with classic tees and button-downs, it's worth it to experiment, mixing in other prints such as polka-dots.

A Plaid Scarf

Plaid can be a bold pattern, but don’t let that keep you from giving it a try. If you’re unwilling to go all out with shirts and bottoms, you can’t go wrong with a plaid scarf. Knotted or draped around your neck, it’s a subtle fashion statement that works for everyone, and will amp up basic outerwear.

A Plaid Bomber Jacket

Bomber jackets for fall aren’t exactly groundbreaking, but they’re certainly one of those outerwear options that never go out of style. If you’ve yet to invest in this laid-back layer, opt for a plaid variation. Pro tip: Size up. You’ll appreciate the extra room when sweater weather comes full-force. 

A Plaid Jumpsuit and a Turtleneck

Of course, investing in checkered outerwear isn’t the only way to layer plaid this season. Another fashion-forward option involves investing in gingham jumpsuits, coveralls, and dresses, styling them over turtlenecks for extra warmth.

A Plaid Hat

Beanie stans, don't @ us, but bucket hats will still be trending for fall 2020. These slightly-oversized, floppy-brimmed, face-framing accessories that LL Cool J made, well, cool, back in the '80s are just as cozy, and three times as roomy as knitted caps. You’re bound to turn heads wearing this type of headgear, but you’re guaranteed to make a statement if you choose a plaid pattern.

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