I'm Aiming to Be More Experimental—8 Outfits Pushing Me Out of My Comfort Zone


(Image credit: @kateemao)

I could live in baggy pants and a basic white tee for the rest of my life, but why play it safe when there are so many great trends to try out? At least, that's my perspective right now as we edge closer to warmer weather. Outfit formulas are super useful and a great tool to lean on if you're building out your wardrobe, but wearing the same combinations day in and day out can start to feel stale. That's precisely why I'm challenging myself to venture outside the sartorial box and try trends and outfits I normally wouldn't go for.

It's not easy to instantly change how I think about getting dressed, so I've assembled a collection of outfits to help me be more experimental. They range from fresh outfit pairings like a dress and baggy pants to quirky accessories I never thought I'd wear in a million years. To see how I'm pushing my style boundaries, keep scrolling for eight unexpected outfits inspiring me now.


(Image credit: @hudashahinn)

Why it's different: These are two staples I'd wear independently but would normally never think to pair together. While layering a button-down shirt underneath a slip dress isn't anything new, the silhouette of this blouse is a bit different, which makes this combination feel especially fresh. 


(Image credit: @abigalemasters)

Why it's different: A plaid skirt is actually the number one item on my spring shopping list, so it's not as "out there" as other pieces. What's unexpected for me here is the addition of an oversized varsity jacket and tall socks. In my head, pairing a plaid skirt with a varsity jacket seems too schoolgirl, but it looks cool and modern with the right proportions and accessories.


(Image credit: @tinamisaghi)

Why it's different: One thing about me: I'll avoid wearing a short skirt at all costs. Don't get me wrong, I love the way they look, but the comfort of a longer midi skirt is unmatched. That said, I've grown to be really into miniskirts (especially since they're having a moment), and I love this sleek approach of pairing them with unique hosiery.


(Image credit: @kateemao)

Why it's different: I've waxed poetic about my love of tweed jackets before, but never would the idea of wearing them with parachute pants pop into my head. These are two pieces I already own, so I'm excited that trying out this new combination will cost me $0.


(Image credit: @lara_bsmnn)

Why it's different: The necktie-micro trend has been on my radar for a while, but until now, I didn't think I could pull it off. However, incorporating it alongside two other staple pieces I already feel comfortable in (the trench coat and the denim midi skirt) makes it seem way less intimidating.


(Image credit: @telshaanderson)

Why it's different: As much as I love wide-leg pants, wearing them with a tunic is new territory for me. I love how this look feels elegant and elevated but still has a cool edge.


(Image credit: @jo.rdan)

Why it's different: The dress-over-pants trend is ramping up this season! The softness of the ruffles and the utilitarian feel of the pants is both a cool contrast and a pairing you don't see every day. 


(Image credit: @maya_nilsen)

Why it's different: Out of all the looks presented here, this is probably the one that diverges most from anything I'd wear normally. Yet somehow, the mix of the cropped trench, cool sneakers, and parachute skirt intrigues me. All of the elements somehow work, and I can't wait to give it a try.

Next up: IYKYK: 31 Cool, Under-the-Radar Items I Found at Nordstrom

Fashion Market Editor

Indya Brown is a fashion editor, stylist, and writer living in Los Angeles. While going to school at Columbia University in New York City, she got her feet wet in the fashion industry interning at Elle magazine, Harper's Bazaar, and New York magazine's The Cut. After graduating in 2016, she joined The Cut as a fashion assistant, eventually working her way up to fashion editor. There, she worked on a multitude of projects, including styling inbook feature stories for New York magazine's print issue, writing and pitching market stories for The Cut, and serving as fashion lead for The Cut's branded content. While New York has been her home for over 10 years, she moved to Los Angeles in the midst of the pandemic in 2020 for a new chapter. Now she is a fashion market editor for Who What Wear, focusing on emerging designers, rising trends on and off the internet, interior design, and BIPOC creatives and brands. Aside from her duties as a fashion market editor, Brown is also a freelance stylist and writer, working on national print and video commercial campaigns for Sephora, The Independent, and Cadillac. Her bylines also include Harper's Bazaar, Vox, and The New York Times. But once the computer goes down and the emails turn off, she's likely eating her way through Koreatown, hunting down vintage furniture, scoping out new outrageous nail designs to try, or taking a hot cycling class.