My sister gave me a really pretty black satin slip dress this summer. She has one too and wears it like a ‘90s kid with a lil’ t-shirt underneath. When I opened the package I was like, “OMG, I love this! I wear rags to bed! This is such an upgrade!” And she was like, “No, dummy, it’s a dress,” (but way nicer than that because she’s nice). Anyway, I tucked the dress into my sock and underwear drawer — because I couldn’t come to grips with the idea of it as daywear — and then one day last week I put it on over a lil’ t-shirt, just like Heather.
“I’m trying to copy your slip dress style today,” I texted her. “But I feel like I’m in drag. Going to keep wearing it and see if I get into it. I do feel cool!!”
“I love it!!!” she wrote back, because she’s nice. She followed up with, “I often feel like I’m in drag.”
We’d both included some laughing-crying emojis to indicate levity, but it struck me that I’d never heard another woman say this before. I asked Heather about it and she said, yeah, as a tall woman, she feels it often, especially when she’s trying something outside her comfort zone.
And yes, that was it. Being a tall woman and trying something new in my dainty slip dress, it made me feel like I was in an over-the-top costume; that I was cosplaying femininity. I 100% felt like I was dressed up as someone else.
When I got my son out of bed that morning, he pushed back in my arms to get a better look at me. Even he could tell I wasn’t dressed like “myself.” My dress was slippery so he was kind of sliding around on my hip, and my belt was creating a funny little footrest for his baby toes. “I’m trying a cool style!” I told him. He smiled and wiggled around on the satin, adjusting his feet to get a better grip on the belt. I guess he was into it.
It’s a weird feeling, being outside your comfort zone in your own clothes. Most days my clothes are a second skin; I wear them with a clear purpose — armor, comfort, confidence, hotness. But wearing something just to wear it, just to see if it works — it was uncomfortable for me. I didn’t know what message my outfit was sending, so I felt self-conscious wearing it around.
This feeling makes it really hard to expand or iterate on my style. Since I started this newsletter in January I’ve definitely rediscovered my love for good outfits but I’ve found myself returning to looks I wore often before motherhood, or at least new versions of them. I’m certainly not experimenting like I once did. I almost never wore the same outfit more than a few times in my 20s, not because I had a million clothes but because I was forever finding new ways to put things together. And in the years I had my fashion blog, I was constantly trying new things and pushing myself to get more creative. I may be dressing cuter now than I was a year ago, but I’m repeating outfits ad nauseam.
I decided to celebrate my little sojourn outside my comfort zone this week with a fashion-blogger-esque photoshoot. I keep looking at these photos to remind myself I can still be creative with my style, even though I’m a mom with an active toddler, a corporate job, and coworkers who only see me from the neck up.

I will probably keep feeling like a drag queen when I try new things but oh well. Drag queens are awesome.
LOVE the Hola Chola jacket!! Looks great on you, chica!