Long Live Katie Dalebout's A-line Skirt
On the podcaster/artist's garage sale find
We were supposed to record for an hour. But then it was almost three hours later and both of us had to pee and we couldn’t believe how long we’d been talking. That’s the magic of Katie Dalebout. I started listening to LET IT OUT almost five years ago, finding her longform conversations soothing and inspiring. They’re best paired with a walk through Prospect Park or a particularly hairy commute. Katie’s voice is calming and grounding, a rare treat in the city.
When I asked her to bring a piece to share on Long Live, I was incredibly honored when she invited on Let It Out in return. You can listen to the episode here and subscribe to her beautiful Substack—LET IT OUT LISTS by
.
This is my ode to a bright colored a-line skirt with pockets. After finding it at a garage sale for $10 it took me months to wear it, partly because it didn’t fit. But even after I finally got it tailored, it wasn’t until I had a mere 10 seconds to choose an outfit for a party that I finally wore it. A style icon of mine who happened to be there complimented my outfit and I’ve now worn it everywhere from work, to my own birthday party, to the doctor to get a giant lime green cast after breaking my leg and it never fails to get a compliment. And one in particular really scratched an itch for me, multiple people have said I look like Carrie Bradshaw when I wear it, which I contribute to how often I now reach for it.
Where did it come from?
A garage sale that my friend Lauren invited me to in my neighborhood.
How much did you pay for it?
$10 for it plus $30 for the tailoring (taking it out in the waist) so $40 total.
How long have you had this piece?
I bought it in February, but it sat in my closet for at least a month because it was too tight in the waist. I could fasten the buttons, but it wasn’t comfortable. I finally took it to the tailor to get it taken out, a somewhat intricate job.
When I picked it up it fit comfortably but I took another month before I wore it because well… I’m an extremist. And in terms of clothes this means I wear them hard. In highschool my mom scolded me for wearing out the same few items while 90% of my closet collected dust. Last summer pals had a joke about the high likelihood I’d be in a certain skirt when they saw me next. Perhaps it stems from wearing uniforms until 8th grade, either way I’ll repeat an outfit with little variance, in a nearly superstitious way. always have been, hopefully always won’t be an extreme outfit repeater…
So in an effort to break the cycle, I considered how the last 4 year’s most worn outfits climbed to that rank.
2020- vintage fisherman sweater with these white Levis
2021- these Doen flare jeans with cowboy boots and this Ozma cardigan and this Beanie
2022- vintage top with these Kamm handy pants and a belt that my friend Dexter was too lazy to return
2023- this Ozma raw silk skirt with this tee (use code ERIKA15 for 15% off)
2023- this Ozma raw silk skirt with this tee
I considered the first time I wore each of these and they were all occasions when I had to get dressed quickly, so without time to overthink it, I risked pairing a, with b, then got a compliment. The sucker for outside validation I am, one, ‘I like your outfit’ from the right person is all it takes. Maybe what people noticed wasn’t so much the clothes but that I felt comfortable in them, meaning they fit me, and likely fit well.
So one night, I put on the garage sale skirt I’d invested in tailoring, and it’s quickly becoming the most worn item in my closet.
How do you wear it?
The night I finally took it off the hanger for the first time, I was heading to a party. A friend was waiting in the car and I had about 10 seconds to choose an outfit. It was a solid occasion to take a style risk. It was a birthday party for a friend I’ve known for 15 years, she’s seen me at my best and worst. I grabbed the skirt, paired it with a cropped white cardigan from Depop, kept on the Docs with white socks I’d been wearing all day, and grabbed a vintage trench coach that doesn’t have a belt because I also got it at a garage sale. And you know what… I think the outfit worked. Actually, I can say it did and here’s why…
The dude driving me never gives me compliments, but he’s basically my style icon. And that night he said: “cool fit,” when I got in the car.
In attendance at this party completely unbeknownst to me was none other than Allison Bornstein who said to me, “I love your outfit, it's so Carrie Bradshaw!” I proceeded to tell her about how I scored it at a garage sale, the tailoring saga, and tried making a fangirl joke like, ‘is this shoe wrong enough?,’ then I passed away.
What does it represent?
It’s still a newer item (to me) so it doesn’t have the sentimental element that clothes that you have memories in do but for now it represents making something your own. I didn’t see inspiration for this outfit, I didn’t search for it like other pieces I’ve desired, rather it found me. It wasn’t quite right, it didn’t even fit but instead of changing myself or wanting to, I changed it to suit me.
I saw its potential-- the pockets, the high waist. These were things I love in a skirt.
The length and the pattern were not something I’d gravitate towards but I gave it a chance. I’m usually a neutral guy, but I let this item stretch me into a territory I wouldn’t go.
So I guess this represents giving something a chance you might not normally. Like with a person, if you have shared values and a connection--everything else is secondary. With an item of clothing, if it’s well made and the silhouette suits you, allow it to stretch you into territory you might not otherwise venture--that’s how we grow.
And to my surprise the sentimental value is now coming to this piece so far I’ve worn it to work a few times, to a party, to my birthday party, and with a blue cast to Capri when everyone signed it. Each time I styled it a little differently: dressed up for my birthday party night with a Ralph Lauren top and tall LoQ boots. With a cropped white t-shirt, a dude friend’s big jean jacket, and a baseball cap. And most recently with a brown tank top, my French Workwaer jacket, and a converse on one foot and a lime green cast on the foot with my broken leg.
I don’t know what this skirt’s story was before me but we’re already begun writing a new one together, and I’m eager to see where we go next and the one that will get written with whoever I end up passing it onto someday.
So now that you’re in love with Katie, too, here are some skirts inspired by her.
The pleating on the Loeffler Randall one makes it super easy to pair with a white tee. ($295)
Imagine this 100% silk option with a cashmere black turtleneck? So good. ($65)
Tiered can be tough, but this one feels incredibly modern for being vintage. I love the smocking detail on the top. ($55)
This skirt gives “not like other white skirts” energy. ($175)
Take the Carrie Bradshaw thing to another level with this J.Crew Collection skirt. ($65)
Another J.Crew Collection option fit for parties. ($45)
I like imagining this with a swimsuit and sandals. ($20)
Incredible color combo going on here. ($30)
Honorable Mentions
These PJs make me feel like a very cozy toddler in the best way. (ERIKA-15 for 15% off)
I’ve had my March Hare watch for two years and reach for it on days when I’m knocking around and want to feel pulled together. (EV20 for 20% off)
Did you know you can always see what pods I’m loving here? Warning: they lean business-y.
Thank you for reading Long Live. It means so much to me. You can shop my favs here, follow along on Instagram + Tiktok, shop my Notion template, and as always, respond to this dispatch for my direct line x
Have you ever had sartorial success at a garage sale?
thank you for having me this was the honor of a lifetime getting to write an ode the this garage sale skirt in my favorite publication!
also I feel like this is the time to come clean that I did purchase the $20 one second from the bottom from my bed this morning…