Published on July 27, 2018 — Leave a comment

How to Wear the Same Pair of Shorts 5 Ways

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When you see a top that catches your eye, what makes you put it back on the racks versus taking it to the register? For all of us at team thrEDIT, the definitive question between an enthusiastic “YASS!” and a hard “Nope!” is, “How can I wear this?”. We’ve challenged our thredUP staffers and influencers to wear a single item multiple ways.

If you haven’t seen our previous challenges, you can check them out here:
We challenged our Brand Marketing Coordinator, Cassandra Moua to wear one skirt, five different ways.
Two fashionistas took on the styleUP challenge dress edition: Stylish blogger Bethany of Twenty Something Plus and Taryn Newton of Glamorous Versatility.
Style/beauty/travel blogger, Kristina, slayed the one T-shirt, five ways styleUP challenge.

Now, it’s Hilary’s turn to styleUP the clothing item that has received the most requests for how-to-wear tips: SHORTS!

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Hilary Pearson is a thredUP graphic designer and our go-to for lookspiration. She’s already mastered the styling of a blazer five different ways, and 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.

HOW TO WEAR 1 PAIR OF SHORTS, 5 WAYS

The Brunch Look

HOW I STYLED IT:

— I love an off-the-shoulder top on a sunny day. The weather’s finally warming up, so I took full advantage. They’re such versatile blouses that can be taken day to night!

— Neutral mules a hat, and a woven bag pulled it all together.

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The Farmer’s Market Look

HOW I STYLED IT:

— I love the frayed details on the hem of this blouse. It gives an otherwise simple top a little bit of character. I found some cute similar tops from Gap as well!

— Topped it off with my favorite hat and classic Birkenstocks.

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The Park Day Look

HOW I STYLED IT:

— 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!

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The Date Night Look

HOW I STYLED IT:

— 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.

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Work

HOW I STYLED IT:

— 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.

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