I have a running joke with myself about high waisted skirts, and it goes like this: I refresh the same three resale searches every single time the weather does that thing Nashville does in October where it’s fifty degrees at 8am and eighty by noon, and I tell myself I’m looking for “the one,” and what I actually mean is I’m looking for the exact skirt I already sold back in 2022 because I decided I didn’t need it. I have made peace with the fact that I will chase that specific skirt for the rest of my life. It is not a real argument. It is just a thing I do, and I know it’s a thing I do, and I keep doing it anyway.
Here’s what nobody tells you about layering a skirt like this when the temperature swings twice before lunch, the waist is doing all the work and the hem is doing none of it. A high waist that actually sits where it says it will means you can pile a tank under a flannel under a jacket and peel off layers all day without the whole thing sliding south, which is the entire point, and I did not appreciate that until I owned one that failed at it.
That one, a synthetic-feeling secondhand find I got for basically nothing because the seller clearly didn’t know what she had, rolled itself down to hip level by 11am every single day like it had somewhere better to be. I wore it four times before I accepted the truth and relisted it myself, at a loss, out of spite.
Hem length is the other thing I got wrong for longer than I’d like to admit. I spent two years buying midi lengths because they photographed well on other people, and then spent every single wearing hiking the thing up to walk normally or sit down without a whole production.
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A hem that actually clears the knee by an inch or two is the one that survives a real day, stairs, a car, a folding chair at somebody’s backyard thing, versus the one that just survives a photo.
And sitting is where the waist tells you the truth about itself. I’ve had one that came back to exactly the same spot after a two hour lunch, and I’ve had one that crept up under my ribs like it was trying to become a bra. You find out which one you bought about ninety minutes in, never sooner.
The gamble pick in my current rotation is a pleated one I bought mostly because I’d been outbid on the exact same style twice and refused to lose a third time. It’s a little much, a little “does this woman own anywhere she’s actually going,” and it is not for someone who wants to disappear into a room. I love it. I also fully understand if you don’t.
