How to Start Taking Risks with Your Style
Featuring seven (or eight, depending on what you count) outfits where I experimented with unexpected layering.
Once, in grad school, a dear friend looked me up and down and asked, “How do you think of these outfits?” I don’t remember what I was wearing that day—or what I wore basically ever—but even now she is adamant that I was wearing red pants and that I replied, “I just try things.”
That’s really the best way I can describe my process, as a person who’s not a fashion professional. Sometimes a fun idea will come to me while I’m falling asleep, like matching two pieces together that I’d previously never thought of. Sometimes I’m inspired by someone else’s outfit innovation and I try to copy them with pieces in my own closet. But usually, the times I’ve come up with something I’m really proud of…I’ve just been standing in my closet for wayyyyy too long, staring at my clothes, thought-spiraling through patterns and equations and measurements until I finally just try something on. Surprise—this is why I’m often late!
In the summer, I get lazier with “just try[ing] things.” I want to wear the least amount of clothes possible in the devilish heat of DC, but that’s also so boring to me. Staple summer pieces like tank tops and shorts are popular because they’re versatile, cute, and easy—and I do wear them all the time—but sometimes I want a little risk. It’s nice knowing I can rely on a tried-and-true outfit, and I reject relying on them all the time.
Inspiration for risk-taking this week came from Elizabeth Tamkin of The Corner Booth, who recently wore a red skirt over a long white button down, so the shirt’s hem peeks out from underneath the skirt; and Harling Ross of Gumshoe, who recently wore a long tunic over a mini skirt, so the skirt just showed. Examples below.
Today you get to be a fly on the wall as I stand in front of the mirror, trying on different outfits. This time, I followed the women above like a good little duckling and experimented with layering unexpected items, like skirts over dresses, just to see what I could create.
First, let’s start with my tried-and-true layering approach that works even in the summer:
I got this dress off of Depop—a vintage little thing I liked the look of. Annoyingly, on its own, it gapes like crazy. It’s a loose dress, it fits just fine, and still I can’t sit without holes showing through its many buttons. I’ve kept it around because it is perfect for layering. I often put a tank top/vest over it to create a new shape, which is not too encumbering for summer. I do this type of layering all. the. time.
My first attempt at the skirt-over-shirt look. Not my favorite. This shirt, while long enough for this type of look, is a little too billowy. I felt like it bunched up in weird places and looked frumpy up top. The only aspect I liked about it was the detail I zoomed in on: a little pattern peeking through the slit in the skirt.
In fact, this shirt/dress has stumped me for a while. I love its purple-gray color, but it doesn’t feel particularly exciting on its own. I decided to try another random layering technique by tying a striped shirt around my waist. People tie jackets around their waists all the time, but that’s more for utility. Here, it’s a deliberate choice to shape the shirt/dress differently, adding new dynamics. I kind of dig it. I don’t know if it’s a summer look, per se, but I could definitely see styling this into a full outfit as the weather cools down.
I decided to try tying the striped shirt around the gaping vintage dress, because who actually cares if the dress gapes? The gaping could give me interesting opportunities for layering underneath the dress. I also wanted to see how it looked with a skirt over it—and I don’t totally hate the look, though I think it would work better with more color. Plus, this look allows me to show off the cute little tie in the back of the dress, which is usually covered up by tank tops/vests in the other ways I style it. It’s a maybe!
I actually really like how this dress looks with a skirt over it, though I do wonder about the bunching in the front. Seems a little out of place? But the bow showing up in the back is so fun. It’s actually just inspiring me to get cuter tops with deeper necklines. I definitely need to up my top game.
I love the colors on this one, but the skirt kind of looks like an apron? I think the dress’s waistline is also a hindrance. So, I thought—why not keep building on this?
It was a fun template to experiment with. I added these two vests and then I got so excited for fall that I distracted myself by lighting my favorite fall candle. I am aware that fall is about eleven weeks away, yeah.
In the end, it was fun to just play around and see what might work for future outfit creations. I definitely think I’ll keep playing with the bright pink/orange dress as a top, and I’ll find some more fun ways to create waistlines on flowy clothing items. I don’t know why I didn’t play more with the hemlines while trying things on, but I could also hide the dresses fully underneath the skirt’s hemline and see how that works. The dress doesn’t have to peek out, even though that’s how I saw it on the looks I pulled for inspiration.
Until I figure out the perfect combination, I’m just a girl, standing in front of her closet, asking it to inspire her. And you are just a fly on the wall, who either perished from repulsion or flew into the closet to find your own fun pairings.
Until next time,
Abi