Published on May 16, 2018 — Leave a comment

How to Wear the Same Pair of Shorts 5 Ways

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Wardrobe essentials are supposed to be your most versatile clothes that can be pulled off the rack and easily styled for any occasion. We can all agree, however, that shorts are the one staple that seem impossible to dress up or down! So how do you wear and style shorts? We decided to recruit our resident fashionista and graphic designer, Hilary Pearson, for another style challenge. She wore a blazer five different ways, now she’ll have to style a shorts outfit for five different occasions! Read on to find out how Hilary takes a single pair of shorts to the farmer’s market, to date night, and even to work! 

I am convinced there are two types of people in this world; those who love shorts and those who don’t. I happen to be a member of the latter segment of the population, which is unfortunate, considering I lived in Texas for 15 years. Even in the dead heat of summer, I always opted for jeans. Yes, I know. I am crazy. Personal style is all about wearing things you feel most confident in. Shorts have never been an item I reach for when I want to feel my best.

When it came time to pick out a pair of shorts to style five ways, I was a little overwhelmed —but in a good way! thredUP has a huge variety of shorts in just about every style you can imagine. In the end, I opted for a charcoal grey, mid-rise pair in a conservative length with a small cuff detail. This provided the greatest flexibility across occasions.

This was, without a doubt, the most difficult style challenge to date, but I am so excited to share these outfits with you. If you don’t love shorts, I hope this will inspire you to step outside of your comfort zone and give them a shot. If you do, I’d love to know what you think of the outfits I put together.



I love the frayed details on the hem of this blouse. It gives an otherwise simple top a little bit of character. Topped it off with my favorite hat and classic Birkenstocks. I found some cute similar tops from Gap as well!

Farmer’s Market

The weather’s finally warming up, so I took full advantage. I love an off the shoulder top on a sunny day. They’re such versatile blouses that can be taken day to night! Neutral mules a hat, and a woven bag pulled it all together.

Park Day

This look was one of my favorites. I loved pairing the shorts with one of my recent vintage T-shirt finds. I grabbed an oversized denim jacket from Gap and threw on a pair of Adidas sneakers… I’m ready for anything!

Date Night

I love wearing oversized sweaters and playing with proportions. The shorts give the look a fresh, modern feel. I went with some low-heeled pumps to give the illusion of longer legs, and tied it all together with a metallic clutch.


Wearing shorts to work can be tricky, but it is possible to pull it off in a polished way —it’s all about balancing coverage. Opt for casual linen or khaki shorts of longer lengths. To style it professionally, I went with a pair of loafers, a lightweight turtleneck, and a long, sleeveless blazer.

Are you up for a style challenge? Tell us how you style shorts in the comments below!