What I Learned from a Week of Adventurous Dressing

Fashion & Style

green outfit ice cream cone kelsey mcclellan michelle maguire wit & delight
“Wardrobe Snacks” – Photo by Kelsey McClellan, Art Direction and Styling by Michelle Maguire

I’ve never thought of myself as an unadventurous dresser, but as I’ve gotten older I’ve realized my everyday personal style is nothing too far-fetched. This isn’t to say I would go the safe route at the Met Gala. I would absolutely stick to the theme. (I say this as a comfort to anyone who wants to invite me to the Met Gala.) But day-to-day it’s linen in the summer and chunky sweaters in the winter. Funky earrings, sure, but never funky socks.

While I love an every-once-in-a-while statement, my regular clothed comfort comes in the form of soft fabrics and classic cuts. I love animal prints…but I got that from my grandma. And isn’t leopard a neutral now anyway?

The thing about attempting to wear outfits you never thought you’d wear is that there are a lot of outfits you think you would wear. No less adventurous (but yeah, different) than what I partook in this week.

My Pinterest boards are full of these looks—photo after photo showcases a neutral high neck top and perfect chunky heel, outfits I know I’d like to wear but don’t for one reason—effort? affordability?—or another. The thing that’s so precious about these looks is the fanciful excitement that comes with them—imagining myself as someone in head to toe silk…there is no better daydream. I do think I would wear those outfits someday. 

I took my week of adventurous dressing as a way to test my limits and see what person I felt like in clothes that were (originally) decidedly not me.

This is not that (Cinderella) story. Instead, I took my week of adventurous dressing as a way to test my limits and see what person I felt like in clothes that were (originally) decidedly not me. Though made up of pieces from my own closet and closets around me, I attempted to put on outfits I’d…never put on on their own. 

Or maybe they were me, and maybe I would put them on on their own. There is a fairytale lesson after all.

Day 1: Green Girl

The outfit: Green pants, green sweater, green sneakers, green sweater, green eyeliner.

green outfit fashion & style wit & delight

I hadn’t thought about it, but with the contents of my closet laid out in front of me I came to the realization that I…love green. I usually love it in a pop, however. Unless I can match my shoes and earrings.

With that being said, this was an adventurous take that was not a stretch. I would do it again in any color.

Still, throughout the day I felt a need to explain myself and my project whenever someone mentioned my outfit (usually in reference to eyeliner—it’s fun, I’ll give it that).

I will say this only happened once, but I felt prepared all along to offer some explanation that was unnecessary.

An early lesson: just wear it, it doesn’t matter, it’s your thing.

Day 2: Print Print Print!

The outfit: Black and white leopard print shirt, regular leopard print linen pants. Loafers, but only because cheetah print boots were missing.

leopard print outfit fashion & style wit & delight

Full transparency: This was a late-game outfit that only made it to my best friend’s house. Of course, this means it was the most fun. 

Thinking I’d be stressed by competing fabrics, I instead felt modish and free. Thinking I’d feel like a fool, I felt like me.

Thinking I’d be stressed by competing fabrics, I instead felt modish and free. Thinking I’d feel like a fool, I felt like me. Would I wear it again? Possibly on a warmer day, to a wine bar, with sandals. If anything it’s a perfect look to watch The Real Housewives in.

Day 3: My Mother’s Daughter

The outfit: Straight from my mom’s closet: a turtleneck and tall black leather boots. From my closet: skinny jeans.

shop your mom's closet fashion & style wit & delight

Tall! Black! Leather! Boots! A staple of mine in fourth grade (borrowed from mom, naturally) that have not made their grand return to my rotation as of yet.

This outfit felt weird to inhabit, but only conceptually. Stepping perfectly into someone’s day to day look is fun on Halloween, but strange when you’re going to work and no one says anything about it.

It’s really comfy to wear your mom’s sweaters though. Would recommend for anyone regardless of taste.

Day 4: My Sister’s Sister

The outfit: Very wide-legged pants, a crop top, Doc Martens, Juicy Couture choker of my own from sixth grade.

tie-dye crop top wide-legged pants fashion & style wit & delight

What started as a ploy to go full-on Euphoria turned into a raid of my 19-year-old sister’s closet who I must admit is not an e-girl. Still, I found pieces that fit the bill. (As I think you should in any 19-year-old’s closet. Isn’t that the fun of it?). 

I was…not at all comfortable in this outfit. The pants were great, but the only time you’ll find me in a three-quarter length tie-dye crop top is if a loving homage-style costume calls for it (and then, I’m not sure who I’d be emulating). 

Adventurous for me? Yes. Will I bring the choker back? No.

Day 5: A Color Story

The outfit: Hot pink tank top, yellow-green cardigan, turquoise satin pants, yellow boots.

colorful outfit yellow cardigan satin pants wit & delight

A far cry from the monochrome that now feels like a lifetime ago, I decided to take every neon or bright piece in my closet and put them to use.

Riding the bus with my decidedly dull winter jacket on top of this outfit was an exercise in juxtaposition. If anything it served to make a gray day brighter.

A lesson: satin pants aren’t linen pants, but they’re comfortable in their own way.

BY Sophie Vilensky - February 21, 2020

1 Comment
Inline Feedbacks
View all comments
February 25, 2020 12:48 am

The article is easy to understand, detailed and meticulous! I had a lot of harvest after watching this article from you! I found it interesting, your article gave me a new perspective! I have read many other articles on the same topic, but your article convinced me
vin lookup

Most-read posts:

Did you know W&D now has a resource library of  Printable Art, Templates, Freebies, and more?

take me there 

Arrow Alone

Get Our Best W&D Resources

for designing a life well-lived


Arrow Alone

the latest

Thank you for being here. For being open to enjoying life’s simple pleasures and looking inward to understand yourself, your neighbors, and your fellow humans! I’m looking forward to chatting with you.

Hi, I'm Kate. Welcome to my happy place.











follow us on instagram @witanddelight_