How to Wear Shorts with Heels

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dallas fashion blogger valery brennan

Well people, there are only two days of summer left. And let me tell you I am just stoked about it! I think this might be the first ever blog post where I’m wearing shorts – and for good reason! I can’t stand wearing shorts!

These shorts were a clearance purchase from Target ($10 woot woot!) and even though summer is technically almost over, we’ve still got plenty of hot days left and I got rid of ALL my shorts a few weeks ago when I cleaned out my closet so I figured I should replace at least one pair.

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Pairing shorts with heels is a great way to make your legs look super long and lean – I love the sandals I wore because they’re chunky and relatively comfortable.

Here are some do’s and don’ts of wearing shorts:

  • DON’T wear stilettos with shorts – sometimes you can make it work but it can easily look a little “lady of the night” if you know what I mean. Unless you’re a shorts and heels pro, I’d stay away.
  • DO mix up the type of heel – round toe pumps, heeled sandals, wedges and heeled booties all look great!
  • DON’T pair heels with Daisy Dukes! You will almost certainly send the wrong message and it’s honestly just not cute. Obviously there’s some flexibility but if your shorts are around fingertip length (you know, the old youth group rule!) then you can probably throw on some heels with them.
  • DO dress it up with a blazer! Shorts, a t shirt, blazer and heels is a fantastic outfit idea, especially if you’re trying to transition to fall but still suffering from hot temperatures.
  • DO wear heels with a t shirt! I know I just said dress it up with a blazer but this is another, more casual idea! A t shirt, shorts and some heeled booties is a cute, casual outfit that will look much more pulled together than tennis shoes (again, please stay away from the stilettos!)
  • DON’T show a ton of skin in other places. This isn’t the time for major cleavage or crop tops, let your legs do the talking today.
  • DO wear them with confidence! This is probably the most important one! Your legs are the star of the outfit so be confident! I promise you look fantastic 🙂

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Remember this shirt? I got it for $1 at the Thrift Giant Outlet here in Dallas! If you missed out, check out my thrift haul video below because it’s also where I got the Gianni Bini heels I’m wearing here and they were only $4.99!


Photos by Stephanie Drenka | Shirt: Thrift Giant Outlet ($1) | Shorts: Target ($10 on clearance; similar here) | Necklace: Bauble Bar ($48; exact) | Heels: Gianni Bini via Goodwill ($4.99) |
Lips: NYX Creamy Lipstick in Narcissus ($4; exact)

I tried to do a “steal my style” for this post but since half of what I’m wearing is thrifted, I couldn’t find anything similar! Get yourself to a thrift store and find some killer heels and a vintage shirt with shoulder pads 🙂

How are you closing out the last few days of summer? Have you full on transitioned to fall or are you waiting for the temps to drop a little more like me?


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One thought on “How to Wear Shorts with Heels

  1. I love the look of hand written calligraphy from Allikdesign. If I could have a custom piece made, I would want it to say some cool movie quote. Something inspirational like “Life moves pretty fast. If you don’t stop and look around once in a while, you could miss it.” or short and sweet like “O’doyle rules!”

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