How To Wear Shorts And Boots Without Looking Like Pretty Woman

January 13, 2017

The dressy short: a fun twist and alternative to a skirt or dress. Sometimes you want a little more freedom for movement but still want to look put together enough. If you are like me, you also try to wear over the knee boots with everything. I am loving the slouchy sweater look and trying something different with a dressy short. The major trick to this is staying monochromatic. I think it’s important to not break up the outfit and keeping it all one color scheme will help the look make sense by staying dressy and put together. This outfit sort of just happened as the pieces are from everywhere. I was obviously on an olive green kick in 2016, so I was able to pair the monochromatic look together perfectly. Actually, I lied as the years post-babies all run together for me. These shorts are H&M 2 years ago and I had worn them once. I loved them and never had a good outfit to wear them with. I know it is definitely hard to find a good dressy short, but that J.Crew and Banana do a good job. But if you ever want to try this, definitely keep the look all one color and stay on the loose fitting side if you are going to wear boots. My new obsession is a slouchy sweater (pair with lace bralets) draping over either a skinny jean or another flowy item like these shorts or a pant.

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sweater | shorts, older H&M, similar here and here until spring gets closer | boots | clutch | bracelet

Short options:

cream short

a similar lace and silk short to mine

Tanks for under sweaters:

Velvet tank

taupy tank

lace tank



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  • Robert Beckwith January 19, 2017 at 11:14 am

    Love this outfit!

    • January 19, 2017 at 12:22 pm

      Sounds like you appreciate a good OTK boot! 🙂

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