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How to Style a Plaid Midi Skirt

3 Days, 3 Ways with

Name: Jenna Murphy
Location: San Diego, CA
Occupation: Middle School Teacher

Style Advice

I believe in the power of the “third piece.” Whether it is a vest, cardigan, blazer, jacket, etc. I always feel more put-together with a piece that brings the outfit together. I love statement clothes with bold prints and colors, especially if they are vintage! I can pair them with basics to let them stand out or mix them together to create fun, eclectic looks. I think getting dressed should be a delightful process. It is often how we begin our day. Whatever you are dressing for, allow it to include something that brings you joy. A cozy fabric, a whimsical accessory, a nostalgic print. Wear what pleases you most!

Style IconS

I don’t have a specific style icon, but I am always inspired by the people I see in real life as well as on Instagram. I always find something to appreciate about a person’s style. I love seeing people’s personalities and creativity come through in their outfits.

Why I picked this Skirt to style

I selected this vintage plaid skirt that I converted to an elastic waist style last fall. I bought it secondhand, but the original wrap style was a little snug. Now I can continue to wear it and enjoy it!
I love the vibrant color palette, and it is a great all-season piece (at least for mild Southern California.) It goes with boots, sandals, sneakers, you name it! It is a comfortable, classic, and versatile piece that I enjoy restyling over and over. 

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Look One: Charming Prints

This outfit is one I wore to work recently. It is great for transitional weather like the early Spring or late Fall. I prefer boots over any other shoe, so I paired the skirt with these leather combat boots I bought secondhand. The socks were a gift, and I love how they match the blue in the skirt perfectly. The orange sweater was a thrift find many years back, and I thrifted the camo jacket in 2020. It is surprisingly lightweight! I haven’t been accessorizing with much jewelry lately, but I do enjoy wearing earrings to work. I like how this outfit is very comfortable but is also interesting with the print mix and pops of color. It is the sort of outfit I need for long days teaching and running errands with my kids after work. It makes me happy when I look in the mirror!

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Look Two: Cool and Confident

This outfit is a more winter-friendly version. The black and leather details help anchor the look while the white ribbed mock neck keeps it cozy. This vintage vest has amazing floral embroidery that complements the skirt and adds a touch of whimsy. The boots, top, belt, and vintage vest are all secondhand finds from online shops. If it isn’t from a thrift store, I’ve found most of my wardrobe on Poshmark, Depop, and thredUP. The jacket is from a rummage sale fundraiser we hosted at the school where I work. I have had these tights since high school, making them almost 15 years old! I feel really confident and cool in this outfit. This is what I would wear if I had something important to do, or if I needed some courage.

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Look Three: California Cowgirl

I love the playfulness of this outfit with its mix of aesthetics, colors, and fun details! The red cowboy boots are one of my favorite footwear choices. They always bring energy to a look! The fringe suede jacket and beaded earrings strengthen the southwestern vibe while the collar and knit top bring a relaxed academic feel. The plaid skirt goes between both styles well, and brings them together in a fresh way. I would wear this to work in a heartbeat! It is another good one for transitional weather between seasons. The boots, jacket, and pink top are vintage pieces I bought through online shops. The earrings and dickey (that’s how I got the collar detail) are both secondhand as well! Even though I am petite, I enjoy the relaxed feel of the midi skirt and loose shirt together. The collar gives it structure but the boxy fit keeps it from being prim, bringing more personality. It’s fun to experiment with “breaking the rules” and I highly recommend it!

See more amazing styles by Jenna:

Instagram: @crafty_thrifting

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