Plaid skirts, chunky loafers, burgundy lips, and the perfect oversized sweatshirt: The best of late-’90s autumn style feels surprisingly right again.

There was something wonderfully unfussy about fall fashion in the late ’90s. We wore plaid skirts with opaque tights, pulled on crewneck sweaters, carried leather messenger bags, and somehow managed to leave the house without a phone permanently attached to one hand.

Most of all, we didn’t want to look like we cared too much. The goal was effortless, a little undone and decidedly unfussy—even if we’d actually put some thought into getting there.

And while we’re not necessarily interested in recreating 1998 from head to toe, plenty of the era’s best pieces have aged remarkably well.

The trick is to borrow the classics rather than wear the decade as a costume. A chunky loafer here. A deep berry lip there. A great pair of black jeans that could just as easily have come from a J.Crew catalog 25 years ago.

Here are some of our favorite finds for bringing a little Last Analog Autumn into the present.

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The Plaid Mini

Rachel Green would approve. A dark plaid mini with opaque black tights is quintessential ’90s, but the combination still looks completely wearable today. Add loafers or boots and a simple sweater rather than piling on more retro references.

Shop: Plaid Mini Skirt, $26.99, Amazon
Shop: Black Opaque Tights, $6.50, Amazon

The Black Honey Lip

Few beauty products say ’90s quite like Clinique’s Black Honey. The sheer, glossy color gives lips that deep berry-burgundy look without the heaviness of a traditional lipstick—and it still feels just as wearable now.

Shop: Clinique Almost Lipstick in Black Honey, $25, Amazon

The Knee-High Boot

A simple brown knee-high boot works with skirts, dresses, and jeans and gives you the ’90s feeling without looking overly nostalgic. In other words, this one earns its closet space.

Shop: Sangeti Boot, $179.25, Vince Camuto

The Chunky Loafer

The chunky loafer is back—although perhaps it never really left. And for the ultimate then-and-now moment, Katie Holmes was spotted wearing this exact Franco Sarto pair in 2026. Wear them with trousers, jeans, or a skirt and tights for a look that feels just as right now as it did then.

Shop: Franco Sarto Carolynn Loafer, $59.99, Amazon

The Flannel Shirt

It wouldn’t be the ’90s without flannel—but you don’t have to go full grunge. Choose a warm autumn plaid and wear it with jeans for an easy weekend look.

Shop: Flannel Shirt, $17.99, Amazon

The Crewneck Sweater

This is one of those soft neutrals that the J Crew catalog would’ve made us want even more by calling the color “oatmeal.” No giant logos, no complicated styling required. Just a really good sweater.

Shop: Crewneck Knit Sweater, $19.99, Amazon

The Leather Messenger Bag

Back when we carried books, paper, and pens, a leather messenger bag was just about the coolest thing going. Happily, it still looks good even if yours now holds a tablet and a phone.

Shop: Leather Messenger Bag, $62.99, Amazon

The Silver Watch

Remember when a watch just…told you what time it was?

A classic silver Fossil feels wonderfully ’90s while still looking completely current—and you won’t receive a single text message on it.

Shop: Fossil Stainless Steel Watch, $120.19, Amazon

The Black Jeans

There may be no easier way to tap into the era than a great pair of straight black jeans. Add loafers or boots, a fitted sweater, and perhaps that Black Honey lip.

Shop: Levi’s Black Jeans, $74.99, Amazon

The Burgundy Sweater

Rich burgundy was made for fall, and a simple, short-sleeved crewneck has exactly the kind of understated ease the ’90s did so well. Nothing fussy, nothing overdone—and definitely nothing that looks like you tried too hard.

Shop: Burgundy Short-Sleeve Sweater, $30.99, Amazon

The Cargo Pants

Yes, cargo pants have returned. This time around, keep everything else simple and let the relaxed silhouette do the work.

Shop: Cargo Pants, $29.99, Amazon

The Oversized Sweatshirt

Possibly the easiest trend revival of them all. An oversized sweatshirt is comfortable, casual, and—with jeans or cargos and a pair of Chucks—just nostalgic enough.

Shop: Oversized Sweatshirt, $24.98, Amazon

The Chucks

Chuck Taylors barely qualify as a comeback because they never really went anywhere. A black low-top pair works just as well now as it did then.

Shop: Women’s Chuck Taylors, $60, Amazon

One Last Look Back

The best thing about revisiting ’90s style isn’t dressing exactly as we did then. It’s remembering how uncomplicated so much of it was: a good sweater, comfortable jeans, a favorite lip color, a pair of shoes we wore until they practically fell apart.

Maybe that’s why these pieces feel so right again. They aren’t only nostalgic. They’re still good.

Want more ’90s nostalgia? Read “The Last Analog Autumn” in the Fall 2026 issue of Pretty, where we revisit the bookstores, beauty, fashion, and little everyday rituals of the last decade before life went fully digital.