High Heels and Shorts: Fashion Do or Don’t?

Heels with shorts are one of those fashion pairings that inspire quite mixed reactions. We’ve seen outfits featuring the combination that we adore, and outfits including the contested duo that feel less than stylish. Clearly shorts length and heel height comes into play, but to clear up the ambiguity around the topic, we enlisted three top stylists to set the record straight.

Scroll down to find out if shorts with high heels can ever look truly stylish, and if so, what the best ways are to pull off the tricky look!

“Heels and shorts are a definite do, when done right! When dressing this look up, pair a short and blazer with a simple pump for a chic summer look.” – Rachel Wirkus

“However, this look is risky and can go wrong very fast, so try not to go very short with the shorts and very high with the heel at the same time. If you can avoid these pitfalls, you have a great summer staple outfit in your hands!” – Rachel Wirkus

“We are fans of heels with shorts. The key is proportion. A great tailored bermuda short with a sleek, thin ankle strap sandal (our favorite being the Stuart Weitzman Nudist) makes for a crisp and linear summer look.” – Wayman + Micah

“This look doesn’t work when paired with super tight cut-off ripped shorts and a formal patent leather evening pump. Consider denim cut-off shorts and evening pumps a great way to guarantee awkward attention.” – Wayman + Micah

“When pairing shorts and heels, it's all about balance.” – Zoe Costello

"If you want to wear your short shorts with a little extra height, pair it with a short (2" or below) block heel sandal. The shorter the shorts the lower the heel. Conversely the longer your shorts, the higher the heel you can get away with. Bermuda shorts can look incredible dressed up with a 4" heel." - Zoe Costello

Our Shorts & Heels Picks:

What do you think of wearing shorts with high heels? Let us know in the comments below!