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Three Outfit Ideas for Pleated Midi Skirts in Fall and Winter featuring the Banana Republic Pleated Midi Skirt :: Effortlessly with Roxy

Welcome back to my one item, three ways outfit series! Previously we tackled how to wear a mini dress in cold weather. Today I’m showing you three outfit ideas for Pleated Midi Skirts in Fall and Winter!

I absolutely love pleated midi skirts. They are flattering on everyone — it’s about finding the right skirt for your shape and style. As a preppy chic girl living in New York City myself I love to take neutrals, add one pop of color, and call it a look. This first outfit has several ideas incorporated into one look styled effortlessly.

We have tone-on-tone with the grey sweater and silver skirt. We have an oversized sweater (this one has cute button accents to give it something special, photos below!). We have plenty of warmth and a chic little bag in a pop of teal blue. All of these combine to make one of my favorite outfits of the moment. Even on the coldest days so far I barely need a jacket over this outfit! And yes, I am wearing nude tights with this outfit to keep my legs warm. 😊

Three Outfit Ideas for Pleated Midi Skirts in Fall and Winter :: Effortlessly with Roxy

Three Outfit Ideas for Pleated Midi Skirts in Fall and Winter :: Effortlessly with Roxy

Three Outfit Ideas for Pleated Midi Skirts in Fall and Winter :: Effortlessly with Roxy
Sweater: Banana Republic (similar 1, 2, 3, 4) | Skirt: Banana Republic
Bag: Chloé (also available 1, 2, 3, 4) | Earrings: Anthropologie (old, similar 1, 2, 3)
Shoes: Loeffler Randall (similar 1, 2, 3, 4) | Sunnies: Express

The key to nailing this first styling is to find a sweater that’s soft enough to come inward towards the waist and long enough to fully clear the hips. If the emphasis on this look is warmth, then the next look is perfect for warmer climates or those days when it’s teasingly warm out.

Three Outfit Ideas for Pleated Midi Skirts in Fall and Winter :: Effortlessly with Roxy
Three Outfit Ideas for Pleated Midi Skirts in Fall and Winter :: Effortlessly with Roxy
Three Outfit Ideas for Pleated Midi Skirts in Fall and Winter :: Effortlessly with Roxy
Three Outfit Ideas for Pleated Midi Skirts in Fall and Winter :: Effortlessly with Roxy
Three Outfit Ideas for Pleated Midi Skirts in Fall and Winter :: Effortlessly with Roxy
Jacket: Blank NYC (also 12, 3) | Cami: Banana Republic (similar 1, 2, 3, 4)
Skirt: Banana Republic | Bag: Chloe (also available 1, 2, 3, 4)
Sunnies: Express | Shoes: Amazon Fashion | Necklace: Madewell (similar 1, 2)
Photos: Allie Provost

A moto jacket truly does go with everything! In this second of three Outfit Ideas for Pleated Midi Skirts in Fall and Winter, I’m once again playing around with tones of grey and white for the main pieces. Then the slightly warmer weather made me feel playful enough to add two pops of color! I am here to tell you that my shoes in this look are incredibly comfortable! No one was more surprised than me; I was planning on grinning through pain but I didn’t need to.

For me as a taller girl (I’m 5’9″, having somehow grown an inch in the last year) I prefer a longer layering cami because camis that are too short tend to make me look stumpy. However if you are on the shorter side or have a longer torso feel free to tuck your cami into the skirt.

Not only is this look great for Fall and Winter, it will work well in Spring too! And in Summer you could easily ditch the jacket altogether for a stylish look. My final look in this series plays around with length, adding a long cardigan to the long skirt for one sleek combination.

Three Outfit Ideas for Pleated Midi Skirts in Fall and Winter :: Effortlessly with Roxy
Three Outfit Ideas for Pleated Midi Skirts in Fall and Winter :: Effortlessly with Roxy
Three Outfit Ideas for Pleated Midi Skirts in Fall and Winter :: Effortlessly with Roxy
Three Outfit Ideas for Pleated Midi Skirts in Fall and Winter :: Effortlessly with Roxy
Cardigan: Banana Republic (super old, similar 1, 2, 3) | Sunnies: Express
Cami: Old Navy (also old, similar 1, 2, 3) | Skirt: Banana Republic
Bag: Rebecca Minkoff (old, similar 1, 2, 3, 4) | Boots: JustFab (similar 1, 2, 3, 4)
Photos: M3 Creative

Sometimes one new piece is all it takes to refresh older pieces in my closet! In this particular outfit only the skirt is new. Everything else is at least a year old. This final of three Outfit Ideas for Pleated Midi Skirts in Fall and Winter illustrates how a long cardigan can instantly add a tailored feel to an unstructured piece like the skirt.

I chose not to belt this particular combination, but I often swap in this skirt and then I do belt the outfit. Something about the pleats here makes me want to have them more open and free to move with the wind.

In selecting a cardigan for this combination, look for one that is about two inches shorter than the skirt or one to two inches longer than the skirt. Don’t wear the skirt with a cardigan of equal length as it will look stumpy rather than elongating. Also plan on tucking in your cami of choice. I went for velvet here but you can easily do silk or any material of your choice.

Ahhh, pleated midi skirts. A complete must-have for any closet! We’re so lucky that in addition to the pretty Banana Republic skirt I’ve featured today, there are so many more gorgeous options out there. Here are some of my favorites that you can put into your own three Outfit Ideas for Pleated Midi Skirts in Fall and Winter. One trend I’m loving right now is pleated midi skirts with pattern that show when the pleats are extended — such as when you walk. So pretty!

25 Pleated Midi Skirt Options to Buy Today

Want even more styling ideas for pleated midi skirts? Be sure to follow me on Pinterest and check out my Street Style board, where you’ll find tons of outfit ideas for pleated midi skirts. Next week in one item, three ways: the denim sherpa jacket!!

50 Comments

  1. Shari
    December 20, 2018 / 10:31 am

    I love all three outfits but prefer the first for my taste. I don't own a pleated skirt as they tend to make those of us with a straighter build look larger but may need to give it a try!

    • December 20, 2018 / 10:36 am

      I used to feel the same way about pleated skirts but I've discovered that it's all about finding the right fit. It's about the right balance of the pleat thickness, how they attach to the waist, length of the skirt and the material used. Have you seen the metallic pleated skirt at Anthro? It would look amazing on you!

  2. December 20, 2018 / 10:39 am

    Ohh I think my favorite is the one with the blue studded heels 🙂 That pop of color is PERFECT!

    • December 20, 2018 / 12:11 pm

      Thank you so much Mei!

  3. December 20, 2018 / 10:51 am

    Midi skirts are all my all time fave. You are so right and they are flattering1 I love the 3 different outfits. Each one is chic and oo I'm swooning over the monochromatic one!

    • December 20, 2018 / 12:11 pm

      They are just so fun to wear! Thanks so much Rach.

    • December 20, 2018 / 12:12 pm

      Thank you very much lyddiegal!

  4. December 20, 2018 / 12:29 pm

    This skirt is so pretty, I love all the ways you styled it!

    XOXO
    Cathy

  5. Liz
    December 20, 2018 / 2:35 pm

    All of these outfits are so glamorous! The first two are my fave and I love how you gave them a different look just by switching up the accessories!

    • December 20, 2018 / 7:25 pm

      Yeah it's easy and fun to use accessories to create totally different outfit vibes!

  6. kelly
    December 20, 2018 / 2:50 pm

    These are great looks; I especially love the cabled sweater with the pleated skirt.

    I also wanted to say how much I appreciate that you feature older items in your outfit posts; I no longer read/follow bloggers that only wear brand new items in every single post (I get that they want to link the items and earn credit when people shop the links, and I have no problem with that, but most regular people re-wear their clothes past the time they are available in stores, so I don't find the all-new, all-the-time outfits to be particularly interesting or relatable). Not trying to knock anybody, just my personal preference is seeing how people re-wear and re-style items they already own.

    • December 20, 2018 / 7:26 pm

      Thank you for this lovely feedback kelly! I hear you and I agree. I suppose on some level it's frustrating when you really like an item you see on someone and discover it's old, but that's also why sites like Poshmark exist. I enjoy seeing items remixed year after year.

  7. Anthropolitan
    December 20, 2018 / 5:02 pm

    Those are good ideas – I hadn't thought to pair a midi with an oversized sweater!

    • December 20, 2018 / 7:26 pm

      Thank you Anthropolitan! It works if you find something that hits just below the hips. 🙂

  8. Christina
    December 20, 2018 / 6:21 pm

    I love your one item, three outfits series–so many good ideas here! Thank you for the inspiration!

    • December 20, 2018 / 7:26 pm

      Thank you Christina! So glad you're enjoying it.

  9. December 20, 2018 / 11:10 pm

    This pleated skirt is sooo gorgeous! I love how you styled it three ways, the first one is my favorite!

    Kileen
    cute & little

  10. Mary
    December 21, 2018 / 4:34 am

    The chucky sweater plus feminine midi skirt is one of my all time favorite combos. This sweater is lovely. I recently purchased a skirt and a sweater from Mango to create this look. I also love the outfit with the grey moto jacket. Great layering.

    • December 21, 2018 / 9:51 am

      So cool Mary! I've been enamored of SO much at Mango these last few months. You're reminding me I need to go take another look.

  11. Melodie
    December 21, 2018 / 8:15 am

    I love these looks; however, the one with the moto jacket is my favorite!

    • December 21, 2018 / 9:51 am

      Thank you so much Melodie!!

  12. Anastasia
    December 21, 2018 / 12:46 pm

    Love these looks, Roxy! Stealing all ideas, especially the second, with the leather jacket and studded heels! I have the most darling blush pleated skirt from Anthro from a few years ago that has just been sitting in my closet — now I can finally give it a whirl!

    • December 22, 2018 / 3:50 pm

      Thank you Anastasia, so lovely to see you!! Excited that this post helped you rediscover an item in your closet!

  13. Emily
    December 21, 2018 / 1:25 pm

    I am all about a midi skirt – they're so chic and feminine!

  14. houseofsequins
    December 21, 2018 / 1:43 pm

    This pleated skirt is gorgeous on you!! I love how you styled each outfit so differently – I can't decide which look is my favorite!

    xoxo Sarah

    • December 22, 2018 / 3:50 pm

      That's the ultimate compliment, thanks Sarah!

  15. December 21, 2018 / 3:14 pm

    I am so living for this skirt! I love all 3 ways you styled it, but the blue shoes are my favorite look!

    • December 22, 2018 / 3:51 pm

      OMG those shoes are heaven! I ordered another pair several weeks back and they should be here in time for my birthday in late January.

  16. Anthro_Blogger
    December 21, 2018 / 4:47 pm

    OT, but does anybody know the name of a recent Maeve blouse with a tie neck and a ruffle that was green with little doggies printed on it? I can't find it on the website and my local store seems to be sold out! It came in many colors but can't remember what the other prints were. TIA!

      • Anthro_Blogger
        December 21, 2018 / 6:04 pm

        Thank you for that link! That's not it, sadly. It had a little U-shaped ruffle around a front yoke and buttons as well. I am at a loss, I can't find it on the website or Google. Hopefully someone bought it and knows the name!

        • December 21, 2018 / 6:28 pm

          I am traveling today but happy to see if I can find the name tomorrow!

          • Anthro_Blogger
            December 21, 2018 / 11:19 pm

            Thank you, Roxy!

          • Anthro_Blogger
            December 27, 2018 / 9:22 pm

            That's it! Thank you so much Roxy!

  17. December 22, 2018 / 12:22 pm

    That skirt is so pretty and obviously very versatile as you've proved! The first monochrome outfit is my favorite though! It's very chic!

    • December 22, 2018 / 3:51 pm

      Thanks so much Deborah!

  18. adriana
    December 22, 2018 / 3:53 pm

    These are all so cute! Loving those skirts – so versatile!

  19. Suzanne
    December 22, 2018 / 5:44 pm

    OMG I'd be freezing in both outfits! YIKES! Definitely need more layering or some sort of outerwear piece. You look so cute tho! Stay warm hahaha xo, Suzanne

  20. ashley hargrove
    December 23, 2018 / 4:08 pm

    Both of these looks are absolutely gorgeous!! I am all for a great pleated skirt for Fall and Winter!! You created some beautiful outfits!

  21. Nataly
    December 23, 2018 / 7:52 pm

    I love a pleated skirt for this time of year! I love the color and the way you styled it here!

  22. December 23, 2018 / 8:25 pm

    I love this pleated skirt on you! I wish I could pull off the trend how you do girl 🙂

    Xo,

    Lauren | lifestylesbylauren.com

  23. Stephanie
    December 26, 2018 / 7:16 pm

    Oooh that first outfits is soooo my jam! I love the cozy oversized sweater layered over the skirt. Such a great way to kind of dress it all down!

  24. December 27, 2018 / 10:06 pm

    Lovely ideas Roxy! I have a couple of pleated skirts and sometimes struggle finding what works best with them, especially in the colder months. I love how delicate the skirt is here too. It pairs so well with everything!

    Sara http://www.mindovermango.com

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