We Asked 3 Women to Wear Something They Normally Don't—Here's What Happened

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In a bit of a fashion rut? You’ve come to the right place. When spring rolls around, we like to do a little sartorial challenge, with daily dares to our favorite fashion girls to step outside of their comfort zones. Who are our daredevils? We tasked Britt St. George of The Relevance Report, Lilly E. Beltran of Daily Craving, and Megan Adelaide Schaefer of Megan Adelaide with wearing bold pieces from J.Crew, which we agree is hardly a big ask! To ensure that this really was a challenge, we made sure to pick new-season styles that are a bit left of center, in terms of our bloggers’ typical looks. Let the challenge begin.

Ready? Set? Go ahead and see how our style set embraced pieces they wouldn’t normally try on.

Challenge #1: Swap an Off-the-Shoulder Top for a One-Shoulder


Yes, the off-the-shoulder look is still going strong, but spring is bringing an update to this trend. Remember those one-shoulder tops celebrities embraced back in the ’90s? They’re back, and to be honest, we can’t figure out why this style ever left us.

That being said, it took Shaefer a minute to decide how to style the pieces, and like all of us, she wondered how a warmer layer like a denim jacket would work over these ruffle details. Turns out, absolutely fine. Her last question: How to wear the loose hem with high-waisted trousers? “Tucking in the top totally solved that problem,” she says, appreciating the confidence of the look. Once a novice to the one-shoulder look, Megan Adelaide is now a devotee.

Challenge #2: Style Textured Flats With a Neutral Outfit


Sandals and sneakers seem to be our go-to footwear choices this time of year, so this challenge was designed to shake up our habits below the ankles. Beltran is with us: She’d usually only style espadrilles with jeans, so being tasked with wearing them with a spring dress was outside the box for this denim lover.

The trick to keeping this look feeling like her was all in her choice of dress, and not just the casual T-shirt style. “Sticking to one color palette helped me maintain my minimalistic style,” she explains. “It helps you try a new look without feeling overly done.” Yet another win for the LBD.

Challenge #3: Incorporate a Ruffle Skirt


Ruffle skirts are undoubtedly one of spring’s biggest trends, but St. George’s style tends to veer away from the frills and toward more minimalistic pieces. Incorporating something so feminine into her wardrobe is decidedly outside her comfort zone.

St. George’s approach? “I used the skirt as my main focal point, and since it’s already a statement piece, I toned [the look] down from there,” she tells us. A pair of simple white tennis shoes took things down a notch, and a knotted T-shirt kept the vibe modern.

Which challenge is the farthest from your personal style, and would you try it? Tell us! 

Jamie McKillop
Branded Content Editor

Who's your style icon?

'90s Cindy Crawford.

What's the beauty essential you can’t live without?

Tea tree oil. 

What's your go-to cocktail?

A dirty gin martini, always.