Amelia Diamond wore a denim skirt every day this week.
I’m Trying to Repair My Relationship With Denim Skirts

No offense to my high school self, but I stopped wearing denim skirts because of her. She ruined them along with a whole assortment of things, like layered tanks and Diet Vanilla Coke. None of that proved to be a loss in my life until last June, when I decided to become a summer skirts person.

The background on the skirts revelation is that I’d never felt right in them, but wanted to. They seemed like such an obvious hot weather wardrobe solution. I like shorts and wear them, but they annoy me for a million reasons, many of which center around the associated complications of extended sittings-down (but also, walking — can’t win). So in the same important but less productive way that I taught myself to be a morning person, I “taught” myself to be a skirt person. Life: a never-ending personal growth journey.

What I never tried last summer was a denim skirt, thanks-but-no-thanks to me at 16. But I was a raw 29 then — not yet a girl, not yet a woman, too unstable in the slow hum of an approaching Saturn Return to clearly see that a trend revisited does not mean I have to revisit the accompanying age, mentally. Now that I am a very mature and clear-headed 30-year-old, however, I feel strong enough to take on such a retroactive challenge. My thinking: Style-wise, I like the look of denim shorts, but comfort-wise, in comparison to shorts, skirts make my knee-up region far happier, so why couldn’t a denim skirt accomplish both?

I gave it a whirl this week and let me tell you something: Once I discovered the refreshing joy of an upwind breeze, and my thighs — their shock collars off, a rolling denim lawn before them — discovered what it meant to be truly free, I think my world changed.

Below, the six skirts I tried that led me to that revelation.

1.The Denim Cut-off Fake-Skort-Kilt, If You Will

A bold first choice, I’ll admit. I wanted to rip the fear-Band-Aid off with this AGOLDE denim cut-off fake skort (no jorts under here, unfortunately). It looks almost exactly like the very denim skirt of my youth that I was avoiding — but with a TWIST! — an asymmetrical wrap-front that confused my boyfriend. If I were a bird, I could have used this as my distraction technique to steal his food or whatever birds use distraction techniques for. Since I am not a bird (sorry, Allie Hamilton), I used it to distract myself from feeling like I was wearing a denim skirt. More of a denim kilt, really.

I wore it with a striped shirt and black ballet flats for a very specific reason: I have tried so many times to wear this exact outfit with denim shorts, a la Alexa Chung, yet never liked how it looked in execution. I wanted to see if a skirt made me feel differently, and it did. So win/win, Alexa: I mastered the outfit, and you now have an identical twin.

2.The Structured A-Line Option

Less of a story for you here, unfortunately. Mostly I just didn’t want to be irresponsible and pretend that all denim is cut with jagged scissors and distressed on purpose.

This skirt is by Eve Denim, and I liked it instantly. I concocted multiple outfits in my head with it, and felt put-together all day. It gave me zero high school flashbacks. Our office has a super lax dress code, but I liked that this one made me feel meeting-ready. In fact, this denim skirt made me feel like an adult; a sentence I never thought I’d say.

3.The Maxi I Didn’t Know I Needed

This skirt is, I suppose, less of a sartorial compromise for the jorts-avoidant and more an alternative option for the woman who doesn’t like the way full-leg jeans look yet wants to try the denim tango. Still, if I wanted to test the denim skirt waters, I knew I had to go all the way in. This look, also a nice denim-friendly-office option, ended up being one of my favorite overall looks (and made me appreciate the versatility of a denim skirt). I’m not trying to rush summer when we’re still technically in spring as I write this, but I can already picture the fall version of this outfit and I’m excited for it.

4.The Casual Midi-Length

Elizabeth Tamkin did all the market for this story; she found me all the denim skirts you see here. She had full creative licensing, and I promised to keep an open mind. When she showed me this Goldsign option, I thought, “Huh.” Then a tumbleweed blew by and that was that.

But then I put it on and realized that this skirt — color, length, weight, buttons — is a missing puzzle piece that I didn’t know my wardrobe was lacking. If it weren’t a sample I’d work it into my weekly no-brainer outfit rotation.

5.The Reminder That A World of Clothes Exists on the Weekend That Doesn’t Involve Leggings

Sometimes when I run weekend summer errands, I look around at all the other people in “real” clothes and think about how nice they look, and how nice it is that they aren’t in the same clothes they’ll later watch a movie in. But then I think about how that seems really hard in practice, mostly because it involves steaming a sundress, pulling the shorts I do like to wear out of the laundry prematurely, or finding a skirt that doesn’t feel too weird to run errands in.

This Gap skirt felt like the perfect length for such casual productive operations.  That’s the nice thing about denim: You don’t have to be too precious about it, you don’t have to “save” it. You pull it on off the floor and wear it.

6.Last But Not Least, the High School Reunion

After five days spent conquering my inner dressing demons, I decided it was time to face the big tuna: a cutoff skirt almost exactly like the one I wore in high school, only this one has appreciably more skin coverage. To go full monty, I paired it with a polo shirt — the polo remained a part of me since high school, but just the thought of pairing both together a week ago would have sent me into a full spiral. Today, I knew I could handle it, and in fact, I was really into the overall look. As fate would have it, one of my best friends from high school came to town this day. She said I looked cute and was not being ironic!

I don’t have any desire to relive my 16th year of life, but sometimes I think about how nice it would be to go back in time to certain scenarios knowing what I know now — how satisfying that would be. This gave me a little piece of that.

Now if you’ll excuse me, I have an English paper to write.

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