Maybe I Am a Skirt Person?
Testing the waters to see if I can pull it off
This might not be the most popular opinion, but I love a city vacation.
It’s not that I don’t enjoy beaches, I absolutely adore every water-related sport and activity (I once kayaked in the ocean while pregnant, which is apparently not advised. No one stopped me, probably because they just assumed I’d eaten one too many burritos). What I am trying to say is beach vacations are great. But I also love getting lost in cities—especially ones with excellent local stores, quirky boutiques, museums that make you feel smarter, cozy cafés, and, ideally, public transportation so good it makes me want to plot moving.
Right now, I’m dreaming of a little escape to Copenhagen and Stockholm. While most people plan by looking up “Top 10 Things to Do,” I head straight to Pinterest and type in things like “Danish Fashion” and “Stockholm Street Style.” Then I clip away at what I find to be chic (even though, let’s be honest, most of these images Pinterest generates are a hodgepodge and have nothing to with Scandinavian style).
The real surprising part? Scrolling on Pinterest actually makes me shop less. Or at least shop smarter. Some of the images on Pinterest are from like 2009, or 2016 so the pieces aren’t in stores currently. Meaning less temptation to copy paste the exact outfit. If I really want something, I’ll usually try Poshmark or The RealReal. But most of the time, I already have something close enough to recreate the vibe.
And while doing this, I noticed something strange: I kept saving images of women in skirts. Which is… odd. Because I made a rule in 2023: no buying skirts.
But Rule Are Meant To Be Broken
Despite my no-skirts decree, I do, in fact, own six or seven skirts. I rarely wear them. But they exist in the corner of my closet. So I started saving outfit images I could replicate, ones that might even convince me to get my neglected pieces out for a twirl.
The key is to find looks made up of pieces you can realistically replicate. They don’t have to be identical. In fact, it’s probably better if they aren’t, especially since you’re unlikely to have the same frame or look as the person in the Pinterest image. What matters is that the outfit follows a formula you’re naturally drawn to and can re-create with ease.
And, in doing this, I ended up with six new outfits, potentially making skirts my new summer personality1.
1. Fancy Skirt + Grey Sweatshirt
Let’s be clear: I am no Jenna Lyons. She can pull off things I wouldn’t dare dream of. She is the queen of the maxi skirt. But the moment I saw this look, I knew I had to try the combo: a flashy skirt paired with the most casual of grey sweatshirts.
I like my version, but the way my skirt falls isn’t ideal, so I hit a roadblock with shoes. If you have a rec, please send help (unless it’s stilettos, then I will respectfully pretend I didn’t see your message).
2. Wrap Skirts For The Win
At one point in my youth, I was obsessed with wrap skirts. The Pinterest inspo image is effortlessly cool. I didn’t have anything identical, but I do have two wrap skirts I designed ages ago—and I loved idea of styling a printed skirt with a basic white tee.
I wanted to go slouchier with the tee, but I didn’t want a bulky tuck situation (hello, visible shirt lines). So I compromised with a middle-ground fit. Footwear still feels like a bit of a struggle, but I’m way happier with the choices here than in the first outfit.
3. Denim + Brown
I’m 99.9999% sure Mimi and I are wearing the same shirt. Hers looks pristine; mine could use an iron and has a coffee stain hidden beneath an embroidered flower (done by me—zoom in for proof).
What I loved most about her outfit was the unexpected pairing of brown with light blue denim. She wore white sandals (which I love); I don’t have any, so I opted for very square-toe mules I had made a few years ago. Slightly aggressive? Yes. But I like the edge they bring.
4. Drama Denim Jacket
This look is in the same vein as the one above, but what caught my eye was the heavily embellished denim shirt paired with a breezy skirt.
I recreated it with my embroidered denim jacket (featuring a dramatic sleeve) and a muted skirt. I could easily swap skirts between this look and the previous one and get a fresh combo, too. And that’s a styling win.
5. Summer Time Black Lace
I love everything about this image of Solange. The skirt? Divine. The shoes? Chef’s kiss. Her skirt is more of a knit; mine is lace. But they’re both matte texture, so I think it works especially for a summer evening.
I styled it first (middle photo) with casual sandals and a structured cotton knit cardigan to make it more Bay Area summer night-time appropriate. The rightmost look might look familiar: in a very similar vibe, I wore the same skirt over the holidays last year with an oversized blazer and heels. What can I say, I love repeating my clothes.
The Verdict: Skirt-Curious
So… maybe I am a semi-skirt person. Maybe. Just seasonally. And only when Pinterest convinces me I could be. But not any skirt, just skirts that are bias cut and/or straight. I know for a fact that I can’t pull off voluminous or A-line ones. NEVER. EVER.
So forget the trends. Are you finding yourself gravitating toward a particular item this summer? How are you styling it? I would love to know!
But wait, there’s more! Part two drops next week, and it’s a good one. Stay tuned!
There are a few affiliate links used in this newsletter which means I may get a small commission if you buy something (at no cost to you). Thank you for supporting my work and trusting my recommendations!