Taylor Swift Just Wore the Skirt-and-Boots Combo That Screams '90s Jennifer Aniston

If there’s one outfit formula I rely on year after year once the leaves start to turn, it’s the tried-and-true skirt-and-boots combo. It’s an easy equation that feels put-together without veering into try-hard territory. And in a recent dinner outing in New York City, Taylor Swift proved that the most foolproof iteration of this look—the mini skirt and knee-high boots—is firmly back on the style map. This isn't just a fleeting trend moment; it's a nod to the enduring, effortless chic of Jennifer Aniston's '90s style.
Stepping out in a pleated Miu Miu mini-skirt and rich tan leather knee-high Jennifer Chamandi boots, Swift channeled a vibe that feels simultaneously nostalgic and perfectly on time for fall 2025. It’s the sartorial equivalent of a perfect autumn day—crisp, classic, and completely effortless. The beauty of this specific pairing lies in its proportions: the short hemline of the skirt is instantly grounded and made weather-appropriate by the height of the boot. It gives you the leg-elongating power of a heel without sacrificing the cool-girl edge that a great boot provides. Oh, and her Cartier jewelry certainly didn't hurt either.
Whether you opt for a sleek mini like Swift’s or lean into the '90s schoolgirl aesthetic with a plaid tartan, all you need to complete the look is a cozy, tucked-in sweater and maybe a subtle swipe of red lipstick. This combo is timeless for a reason—it’s polished, versatile, and requires zero complicated styling. Keep scrolling to shop pieces to re-create Swift's easy fall outfit for yourself.
On Taylor Swift: Miu Miu skirt; Dior bag; Jennifer Chamandi boots; Catbird ring; Artifex Fine Jewelry ring; Cartier bracelet and watch
Shop Taylor Swift's Exact Cartier Bracelet
Shop Pieces to Re-Create Taylor Swift's Look
Drew Elovitz is originally from Pittsburgh, Pennsylvania, but has spent the last decade living and working in New York City. She earned a master's degree in media and popular culture from New York University, then began her career on the internet as the Twitter voice of Barbie. She worked previously atBest Knockoff Luxury Clothing as the director of content strategy and also spent several years leading the social media teams at Teen Vogue and Entertainment Weekly. You'll find her byline on the site around topics such as celebrity fashion, must-have basics, beauty favorites (particularly nail polish), and wellness tips and tricks.
-
These FP New Arrivals Are a Fashion Person's Fall Dream—34 Items You'll See in the NYC Streets
The ultimate shopping temptation.
-
6 Fall Outfit Formulas I'm Stealing From Zoë Kravitz
Effortless, polished, and sophisticated.
-
Why Did I Wait So Long to Buy Into This Rich-Looking Jacket Style?
Now, it's in my fall rotation.
-
If You Live in NYC, You *Should* Know That the Chicest Way to Wear a Miniskirt and Tights in Fall Is With This Elegant Shoe Color Trend
It's not black pumps or white sneakers.
-
Forget Silk Scarves—Fashion People Everywhere Are Tying This Fall Essential Around Their Waists Instead
You probably already own it.
-
Live From Madrid: 31 Zara and Mango Finds That I Guarantee Will Soon Sell Out Stateside
Straight from the motherland.
-
Looking Parisian in Paris Is Only Doable If You Own These 12 Fall Wardrobe Essentials
Buy them; look French. It's as simple as that.
-
A Rich-Looking Closet Is the Vibe—These 30 Amazon Picks Surprisingly Fit the Bill
See the affordable yet chic finds.