How to Wear: a Skirt Over Pants
without looking like you’re ready to accept your Teen Choice award
This is a safe space for people who know every word to the Lizzie McGuire Movie soundtrack. I’ll always have a soft spot for the Y2K fashion I was raised on, but as a 33 year old in the year 2025, my style leans more “please pay me to do this job” than “I’m ready to get Slimed!” And yet, my look of choice actually involves wearing a skirt over pants pretty often - just maybe not in the way you’re imagining.
The current divisiveness of this look definitely stems from the dark shadow of the aughts iteration of the SOP (Skirt Over Pants), aka the infamous 2000’s SOJ (Skirt Over Jeans). It was deliberately incohesive, relying solely on the so-called shock factor of an “unexpected” clash by simply adding jeans to an outfit that never really called for jeans.
The look was the opposite of styling, a symptom of the illness that was being a Millennial Cool Girl. At the time, being chill was priority number one. Nothing doomed you to uncoolness like Trying Too Hard and Caring About Things. One of the best ways to achieve perpetual nonchalance was by always wearing jeans. Who cares about this awards show? I’m literally so chill right now. I wore jeans.
The thing is, wearing a skirt over pants will always be cringe. It’s technically too many clothes, it’s usually unnecessary, it’s outwardly concerned with the visual aesthetic. But in order to pull it off, you have to embrace being cringe. Wearing too many clothes and being outwardly concerned with your visual aesthetics have absolutely no moral value, regardless of what any snarky comments may imply.
What I’m not personally looking to emulate, however, is the very specific brand of cringe that was being Quirky™ in 2003. If anything, I’d like my style to signal that I am, in fact, like other girls. I think other girls are fun and brilliant and beautiful, and I’d like to be associated with them. I’m never wearing a skirt over pants to signal nonchalance. I’m wearing a skirt over pants to let you know that I am, actually, very chalant.
The Vintage Inspiration
Before the highly questionable styling of the early aughts, there were decades of truly inspiring SOP wearers. You know that photo of Ashley Tisdale up there? Erase it from your memory. Replace it with this:
FRUiTS (1997-2017)
Photographer Shoichi Aoki’s legendary Japanese fashion magazine played a pivotal role in street style as we know it today. The magazine featured full-page outfit photos with short profiles of people Aoki considered outside of mainstream fashion. The publication is credited for opening up Japanese fashion subculture to the West, and many of its incredible looks featured skirts and dresses over pants.
1950’s Hostess Dresses
Of all the things mid century America got wrong, they did squeeze in some certified bangers. For a brief moment in time, housewives across the country flitted around their living rooms in Hostess Outfits. These dresses and skirts were typically floor length and dramatic in style, but made of the casual fabrics and finishes found on robes and pajamas. The resulting looks were glamorous but relaxed, the perfect way to dunk on your guests by looking better than them while still being more comfortable.
One iteration of this look was a gown or floor-length skirt that opened at the front to reveal slim, cigarette style trousers.
Similar styling was incorporated into other looks through the following decades, and made a brief resurgence on runways in the 2010’s.
Runways of the Late 1990’s
It’s pretty incredible to think that these stunning looks were put out just before ruffled skirts were being pulled over boot cut jeans. How did we stray so far so quickly?
Now that we’ve had a palette cleanser - let the chaotic layering commence!
Things to Consider
Some general guidelines that will apply to most of the styling ideas in this letter:
I think a long skirt is the easiest to style over pants, followed by a mini skirt, with a midi skirt being the most challenging.
Not all shapes & textures work for layering. Your skirt can be any length, but will often sit better if it’s either somewhat structured (pleated, A-line) or very flowy (chiffon, lace). I find that fabrics that are clingy (jersey, satin) or stretchy (knits, spandex/Lycra) often bunch, ride up, or look lumpy if your pants aren’t super smooth or form-fitting. A good outfit shouldn’t require constant fussing.
Make it comfortable. One of the reasons I consistently return to this style is because it physically feels good for me to wear. If you don’t feel your best in a lot of layers, this might not be for you. If your attempt at this needs frequent adjustments, or the pieces sit on your body unnaturally or don’t move well, you probably need to rethink your styling.
Utilize your sluttiest skirts! Sheer fabrics, super high slits, cutouts, and micro-minis lend themselves really well to this kind of layering. If you’ve ever found yourself looking at a skirt (or dress) and wondering how the hell to style it without showing cooch, pants might just be your answer.
Your shoes are not an afterthought. If you’re intentionally matching, you may want to consider extending that match to your footwear. High contrast shoes have their place, but they can also break up smooth lines or create tension where you’re not looking for it.
LEVEL: EASY
A Really Long Skirt
If the idea of wearing a skirt over pants still kind of freaks you out, start here. The longer the skirt, the less pants anyone is going to see. If you’re just trying to stay warm, this is very practical styling. You can put pretty much anything underneath a big ass, long ass skirt (especially paired with tall boots), including ugly but very pragmatic stuff like long johns or sweatpants.
If you kind of want people to know you’re wearing a skirt over pants, start with the loose on loose combo. Loose, flowing pants underneath a loose, flowing skirt will create a shape that reads like a layered or tiered skirt when you’re standing still. Once you start walking, the pants should create just enough space under the hem of the skirt that there’s a little surprise in your movement. This is my favorite kind of styling - subtle and approachable, while still creating a sense of intention. Most people probably won’t even notice the pants, and the ones that do will be confused, inspired, or hopefully some combination of both.
Not Quite A Skirt
If you’d rather dip a toe than do a full on cannonball, you can start by creating SOP proportions with other garments. Long coats, tunics, dusters, peplums, and other lengthy tops can mimic the shapes of a skirt or dress, giving you a similar silhouette.
All Black (or your equivalent)
Here in NYC, wearing all black is about as inconspicuous as you can be. It has a uniform-like quality that gives you space to play in a controlled setting. When you eliminate the visual contrast created by multiple colors, the friction of mismatched textures and shapes are less jarring. By letting go of the worries about pairing colors, you have room to explore the other elements of your clothing.
If you live somewhere in which wearing all black gets you jokes about The Matrix, this may not be a starting point for you. However, you may have your own version of “wearing all black.” Ask yourself what pieces or styles feel comfortable, easy, whatever other adjectives you’re looking to use to describe your style. How do these items go together? If you gravitate towards t-shirts or athleisure, you can absolutely start there.
LEVEL: MEDIUM
Keep reading with a 7-day free trial
Subscribe to 1-800-VINTAGE to keep reading this post and get 7 days of free access to the full post archives.