Being a painter, I have a uniform of sorts--comfortable, solid colors, boyish. Fashion, although interesting, has always left me intimidated. But after realizing several months ago that I was only wearing a tenth of my wardrobe, I decided to purge and branch out a bit, just to see what happened.

I asked friend and San Francisco-based wardrobe stylist and style expert Caroline Rooney for advice on this project. Before I knew it, she was standing in my bedroom observing my closet. There’s something about having someone assessing your clothes that is a little unnerving. I hadn’t realized how much insecurity is tied up with our wardrobes. But talking with her was like a breath of fresh air. Being one-on-one allowed us to pick up parallels between her world of fashion and mine of fine art.

For one, Caroline educated me on the composition of clothing. She took each article and assessed its symmetry. Was it asymmetric with one pocket or symmetric with two? She pointed out symmetry represented masculinity in its square geometric form. As Caroline’s expertise lies in menswear and as I’ve always been a bit of a tomboy,  I could relate wholly to her masculine approach to style. Plus, she asked similar questions I ask when painting. Where is the eye drawn to? How do color and texture relate? It didn’t take Caroline long to scope out my outfits and come up with a plan.

The ultimate goal was to create a wardrobe that contained suitable pieces to mix and match and layer for all occasions. We planned this project around my two week-three city trip--from LA to NYC to DC and back--in late June. The idea was to choose pieces that I’d wear on the trip, but that would also work as mainstays in my wardrobe when I got home. Caroline told me it was ok to re-wear pieces while traveling and to take basic comfortable pieces to dress up or down. I liked her practicality and thoughtful construction of each outfit.

In New York I did a mini photo shoot with a wonderful photographer I found on Instagram to record our collaboration and to reflect on everything I’d learned from Caroline. Initially I had expected to come away with new perspective on wardrobe construction; but I didn't expect this project to act as a mirror. The clothes we wear represent us. They speak before we do. What we’re interested in and what we choose to hide come through the messages our clothing tell. I found that I prefer to wear muted colors since I work with bright paints every day, and that I’m curious about shape and texture. I prefer to downplay my arms and hips when I choose clothing--which may be why I like more masculine styles. So much of this project was delving into my own insecurities and finding new ways to be comfortable--be it through asking for help or choosing clothes that are right for your life.

Pictured: VEDA Paradiso Dress

Highlights from Caroline

  • Composition, silhouette, and proportion are the most important things to consider when putting together an outfit.

  • It's important to consider your personal style, but even more importantly, understand your body and the way that certain pieces go together to flatter your unique shape and help you feel confident.

  • For a night out look, wearing pieces that make you feel confident and beautifully pulled together will help you feel more sexy than wearing an uncomfortable short dress you're worrying about (and uncomfortable in!) all night.

  • Remember that it's absolutely okay to wear things multiple times, and be realistic about your itinerary when you're traveling. Opt for pieces that you love wearing at home (so they won't be intimidating in a new place!) peppered in with a few location specific pieces.

  • I always advocate for basics, first and foremost, so start by picking out your favorite every day pieces, and then pack special items for the events or activities you'll be doing during the trip.

New Compositions: A Look into Fashion | Heather Day
New Compositions: A Look into Fashion | Heather Day

Caroline Rooney is a San Francisco-based wardrobe stylist and style expert. She believes in making fashion less intimidating by creating wardrobes focused around well fitting, elevated basics, and peppering in trend items and bold pieces seasonally to compliment clients' personal style. Caroline works with private clients in the Bay Area and on-site photoshoot collaborations. She’s styled for Google, Apple, Levi’s, Mark & Graham Neiman Marcus and Macy’s. You can find her at CaroRooney.com and on Instagram @CaroRooney.

A special thanks to the companies who supported our collaboration. Many of the pieces were gifted to us and we wanted to express gratitude for their support. Another thanks to the generous hotels that hosted me in New York: The Time New York Hotel, The West House Hotel and The Quin Hotel.

Written by Heather Day. Edited by Kate Holthouser.  Photos by Emily Hlavac Green. Some of the paintings you see in these photos will be available in my solo show in San Francisco this fall.