Stylish Plaid Outfits To Wear To The Office This Fall

Updated: Dec 29, 2020

Plaid blazer layered over a black roll neck top and a fitted black pencil skirt

As our summer dresses and beachy sandals take their final bow for the the new season, I've started to plan out "chilly weather" workwear outfits. Knee high boots, chunky knit sweaters, and colored leather trench coats will be in our rotation.

But if you're seeking striking patterns to mix in with your fall essentials, plaid outfits is the top must have for 2020. This preppy print is a timeless print that combines perfectly with other fashion workwear staples. Check out these posh plaid outfit combinations to try for yourself.

Plaid Skirt Styled With a Chunky Knit Sweater

Pair up a chunky knit sweater with a plaid pencil skirt. Level up the look with nude pumps. Complete the look with a classy clutch or pouch in a bold or neutral color. Preferably chestnut, tan, or dark brown. Lastly for jewelry, opt for thick mini hoop earrings!

Budget Friendly Stylish Fall Workwear Essentials To Add To Your Wardrobe


  • Oversized Ruched Clutch Bag In Brown: Asos

  • Thick Mini Hoop Earrings: Express

  • Fort Knox Bracelet: Shopbop

  • Plaid Pencil Skirt: Banana Republic

  • Hazel Pumps: Shopbop

  • Statement Turtleneck Sweater: Nordstrom

Plaid Blazer Over a Roll Neck Top and Fitted Black Skirt

For my featured workwear outfit I wore a roll neck top and a black fitted pencil skirt. I layered a stylish (must -have) boxy double breasted plaid blazer on top. This blazer that I bought from H&M is very loose fitting. I like my blazers boxy, but not to the point where I feel like I'm drowning in it. So I had to go down three sizes as crazy as that sounds. I'm normally a small. but the small looked huge on me. So I tried on a few other sizes, and surprisingly the XXXS fits just the way I like it. I would strongly advice you to do the same, because sadly this lovely blazer does not fit true to size.

Finally I complemented the look with shocking red sock booties. I bought these from Nordstrom rack at a bargain price. The original price was $69.99 and I paid half the price. They are very comfy to wear and fits true to size. I tied the look together with a black embossed clutch and silver statement stud earrings!

Top favorite work wear choices to create the same exact look.


  • Red Sock Bootie: Nordstrom Rack

  • Black Embossed Clutch: Lulus

  • Square Fringe Drop Earrings: Express

  • Knit skirt: Nordstrom

  • Double-Breasted Blazer: H&M

  • Fitted Ribbed Turtleneck Sweater: Express

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