WE’RE DRESSING LIKE IT’S 1999 - AGAIN
When it comes to nostalgia, especially with the 90s, there is a part I really want nothing to do with. Please keep the butterfly clips, the frosted tips, those stabby headbands that gave us all headaches on picture day, and matching velour tracksuits because I’m not about trying to pull off a Jennifer Lopez. I’ll leave all those to the internet and the Gen Z crowd who think they are just discovering them.
There is another version of the 90s making its way back around through the runways and into online shopping carts, and it’s much harder to dismiss. It’s not the maximalist chaos mentioned before, but rather, the quieter, more wearable stuff. The pieces you could theoretically style today without looking like you raided a time capsule or are desperately trying to hold on to your youth. You know, how we felt our parents were doing with the 1980s for a time. With all of the hype about the 90s coming full circle, and it feels like I talk about this every 4 months, these are the pieces that I think are actually worth paying attention to, because if you’re going to do it, do it right.
The Handkerchief Haltertop Situation
I had a handkerchief top in middle school, except mine was more of the halter top situation. Still not entirely age-appropriate, but it’s not like I got to wear it to school, and besides, everyone had one, right? Being an adult now, this is a completely different conversation. If I wanted to tie a silk scarf into a tiny top, I absolutely could. Silk scarf prints and proper halterneck construction of today read much more intentional than “found this at a flea market.” The difference is how they are styled. Maybe you wear them with capri pants - I never will, or maybe you’re more likely to choose wide, fluid trousers for effortless drama. Something that says Chloé, not spring break 2003.
I think at this stage in my life, 11 times out of 10, I’m going to run for a halter top rather than anything having to do with a handkerchief or scarf, but that’s just where I’m at. I’ve always been a halter top girl. But if you’re into the silk scarf revival, the next logical step for you is likely turning it into a top or at least getting a top to add to your closet.
Velvet Halterneck Top
Halter-Neck Lace Top
Eyelet Haltertop
Scarf-Print Tie-Neck
Silk-Satin Halterneck Top
Halter Neck Handkerchief Top
Denim Cutoffs
Full transparency here: I never gave up on denim cutoffs, whether the trend “passed” or not. Every summer, I always try to make other shorts work. I’ve tried Bermuda, linen, denim, and a really interesting houndstooth pair that ended up feeling much more fall than summer, and every summer I end up going right back to my regular denim cutoffs. They are just easier and frankly much more my style.
Turns out everyone else is just catching up. Classic denim shorts - the shorter and more worn in the better, duh - are the move this season. And they’re being styled in a way that pushes them past “day at the beach” territory, you may think they are stuck in. Pair them with something that contradicts their casual energy: a structured belt, moto boots, a crisp button-down. Isabel Marant has been doing this for years, but now its mainstream moment has arrived.
Pamela Anderson, Kate Moss, and Cindy Crawford all made denim cutoffs look like the only thing worth wearing. It took us many years to figure out they were right, but at least we learned from the best.
Mid-Rise Denim Shorts
Le City Shorts
Vintage Mid Shorts
High-Waisted Curved Shorts
Distressed Denim Shorts
Reworked Shorts
Jelly Shoes
This one I wasn’t really ready to defend, and yet here I am. Jelly shoes were the domain of seven-year-olds and beach vacations in the 90s, which made them feel like the last trend I’d expect to see seriously being reconsidered. Then Chloé went and made a pair that costs more than a car payment, and suddenly jellies were a whole thing. The key is the silhouette. You don’t have to choose the flimsy style that left blisters in a million places and smelled like chlorine by August. The versions coming back now are Mary Janes, fisherman sandals, strappy flats, and other structured options that feel more considered.
Ancient Greek Sandals does a translucent aqua version that is truly an option I’d consider; meanwhile, Melissa has been at this for years and keeps getting better. I’m not saying make them your go-to sandal for the summer, but I’m just saying give them a second look. Just remember, your parents aren’t going to listen to you complain this time.
Jelly Mary Janes
Jelly Sandals
Jelly Ballerina Shoes
Barcelona Jelly Flats
Jelly Fisherman Sandals
Jelly Thong Flat Sandals
The Skirt Suit
When I was in 5th grade, I won’t say what year that was, I dressed like Cher Horowitz for the whole year. I’m not joking. Pleated skirts, the whole 9 yards. So it’s safe to say I have a bit of love for The Skirt Suit, and I am pretty excited that they are back at a more age-appropriate time, ha. For about a decade, the default for women’s tailoring was: big blazer, wide trousers, and pretty much anything that vaguely looks like you borrowed it from a man 2x your size. It worked, and it still works when you want it to. Trust me, I have blazers that fit directly in this category.
But the spring runways had a bit of a shift, and it has everything to do with the bottom half. Pencil skirts, coordinated minis, and column silhouettes, oh my.
Thom Browne, Max Mara, and, of course, Chanel, all sent versions down the runway, and all made the case for it without really needing to say a word. It’s not replacing the trouser suit because nothing can replace a good trouser-based suit, but it’s a genuinely exciting alternative for anyone who’s been dressing exclusively from the waist up.
The Bottom line
Fashion nostalgia is easy to be cynical about. Everything comes back, and usually the worst parts come back loudest because that’s what gets the clicks. What I appreciate about this particular round of 90s revisionism is that it’s reaching for the pieces that actually aged well. The ones that make sense then and still make sense now just slightly reframed. A skirt suit that fits like it was made for you rather than a prop or denim shorts that don’t require some 10-step internal debate to justify wearing, and of course, jellies that, okay, require a little courage, but will pay off.
None of these are desperate grab at a decade that is long gone. They’re updates, and that’s the difference between something worth buying and something worth scrolling past.