OOTD: Leggings & Short Dresses

In the past I never liked wearing leggings with dresses, but for some reason this season I’m kind of loving it and have been wearing…


In the past I never liked wearing leggings with dresses, but for some reason this season I’m kind of loving it and have been wearing them multiple times a week with different dresses and tunics. Since I am 5’4″, I find myself most likely this style with what I call “short” dresses, those that would land above my knees.

My first look is with this Evans asymmetrical dress, which I love lots (and is now $37). I wear this dress pretty often either with a belt and jewelry or without those things and a scarf instead.

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I also like to wear the leggings with more colorful pieces. I picked up the following dress from Gwynnie Bee. It’s not my usual kind of print/shape, but I actually really, really love it (sorry the pics aren’t great on any of these). Unfortunately in both pics I have my hand over the tuck on the side, but that tuck also gives this dress a slightly asymmetrical angle, which I’m kinda into these days.

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How do you wear leggings? I need some more ideas because wearing leggings is truly so, so comfortable!


  1. Oh, the Gwynnie Bee dress is adorable! I love leggings with shorter dresses. With boots they look great, but with shoes I found leggings looked sometimes a bit ‘wrong’, especially if they were a little long on the ankle. It’s taken me over a year of looking at photos of myself to realise if I shimmy my leggings up a few inches so they look halfway between cropped leggings and normal leggings, they look fine with shoes. Sometimes I’m not so smart. 😉

  2. I really like wearing leggings with a tall boot. I got a pair of leather (faux) paneled black leggings that are insanely comfy that I pair with a tall black boot and wear them to work. I feel like I’m in my pjs. It’s crazy!

  3. I wear leggings with both dresses and skirts. Now in the winter they are long and i wear them with boots. Either plain black boots or studded! I sometimes like a little color on the leggings, since I mostly wear black clothes. I have a pair from ASOS in teal and one that I just bought from PinkClove in blue and black “scottish pattern”. I also love wearing the teal leggings with a denim skirt in knee length! In the summer I like the leggings cropped and with a pair of wedge sandals.

  4. I signed up with a Gwynnie Bee account because of your blog and after i finish that comment, I’m going to go find that green dress!! It’s so cute!
    Because of my love of dresses and the foot of snow on the ground, I wear leggings almost every day. My favorite leggings are from Forever 21 they don’t fade and they maintain their shape even after being stretched all over my ample lower half. But mostly because I can get fun prints. I am right now wearing a pair of black and white tribal print leggings with a basic, short, black dress and ankle boots and it’s my most favorite outfit ever. Because, yes, soooooo cozy!

  5. So in love with that Gwynnie Bee dress! I tend to wear leggings with a tunic, I tend to find them too bulky with dresses, and I don’t like to wear leggings with just a top, so I tend to go for a tunic that will cover my butt!

  6. You look so fab in both dresses. <3

    At home I simply wear them with a tee or a jumper. Outside mostly combined with dresses or long oversized jumper which looks like a short dress. 🙂 xoxo

  7. Rebecca, where are your leggings from? I have Old Navy ones and they don’t hold their shape, which is disappointing when I’m tryna look cute!

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