Taylor Swift Recently Rocked the Skirt-and-Boots Ensemble That Shouts '90s Jennifer Aniston.

Taylor Swift Recently Rocked the Skirt-and-Boots Ensemble That Shouts '90s Jennifer Aniston.

      When the leaves begin to change each year, one outfit formula I count on is the classic skirt-and-boots pairing. It's a straightforward combination that looks polished without trying too hard. In a recent dinner in New York City, Taylor Swift showcased the most dependable version of this style—the mini skirt teamed with knee-high boots—asserting its firm place in current fashion. This isn’t merely a passing trend; it reflects the timeless, effortless elegance reminiscent of Jennifer Aniston's '90s looks.

      Wearing a pleated Miu Miu mini-skirt and luxurious tan leather knee-high Jennifer Chamandi boots, Swift embodied a style that feels both nostalgic and perfectly suited for fall 2025. It's akin to the ideal autumn day—crisp, classic, and entirely effortless. The beauty of this particular combination lies in its proportions: the skirt's short hemline is balanced and made suitable for the season by the height of the boots. This pairing provides the leg-elongating advantage of heels without losing the cool-girl vibe a great pair of boots offers. And the Cartier jewelry she wore certainly added to the appeal.

      Whether you choose a sleek mini like Swift's or embrace a '90s-inspired plaid tartan, all that's needed to complete the look is a cozy, tucked-in sweater and perhaps a subtle touch of red lipstick. This combination is timeless for a reason—it’s refined, versatile, and requires minimal styling effort. Keep scrolling for pieces to recreate Swift's effortless fall outfit for yourself.

      (Image credit: Getty Images) 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:

      Cartier

      Love Unlimited Bracelet

      You'll love Cartier's iconic Love collection.

      Shop Pieces to Re-Create Taylor Swift's Look:

      Good American

      Weightless Turtleneck

      These great basics by Good American are a sure bet.

      Choose your favorite plaid.

      J.Crew

      Stevie Knee-High Boots in Suede

      J.Crew offers a fantastic selection of boots right now.

      Marc Jacobs

      The Mini Dual Top Handle Bag

      A stylish bag for your next night out.

      Splendid

      Classic Turtleneck

      Splendid uses the softest materials.

      WAYF

      Darby Plaid Pleated Miniskirt

      Plaids in neutral colors coordinate with everything.

      Tory Burch

      Lee Radziwill Smooth Top Handle Petite Bag

      We're fans of the petite Radziwill top handle bag.

      Sam Edelman

      Sylvia Knee High Boots

      We'd consider getting these boots in multiple shades.

Taylor Swift Recently Rocked the Skirt-and-Boots Ensemble That Shouts '90s Jennifer Aniston. Taylor Swift Recently Rocked the Skirt-and-Boots Ensemble That Shouts '90s Jennifer Aniston. Taylor Swift Recently Rocked the Skirt-and-Boots Ensemble That Shouts '90s Jennifer Aniston. Taylor Swift Recently Rocked the Skirt-and-Boots Ensemble That Shouts '90s Jennifer Aniston. Taylor Swift Recently Rocked the Skirt-and-Boots Ensemble That Shouts '90s Jennifer Aniston. Taylor Swift Recently Rocked the Skirt-and-Boots Ensemble That Shouts '90s Jennifer Aniston. Taylor Swift Recently Rocked the Skirt-and-Boots Ensemble That Shouts '90s Jennifer Aniston. Taylor Swift Recently Rocked the Skirt-and-Boots Ensemble That Shouts '90s Jennifer Aniston. Taylor Swift Recently Rocked the Skirt-and-Boots Ensemble That Shouts '90s Jennifer Aniston. Taylor Swift Recently Rocked the Skirt-and-Boots Ensemble That Shouts '90s Jennifer Aniston.

Other articles

I wasn't keen on polka-dot nails—until I came across this sophisticated design. I wasn't keen on polka-dot nails—until I came across this sophisticated design. I can't seem to get it out of my mind now. Case Closed: Women in Paris Have Just Announced This as the Only Coat Trend That Counts Case Closed: Women in Paris Have Just Announced This as the Only Coat Trend That Counts It's very stylish. Victoria Beckham recently donned the sophisticated anti-flat shoe that adds an intriguing touch to a monochrome ensemble. Victoria Beckham recently donned the sophisticated anti-flat shoe that adds an intriguing touch to a monochrome ensemble. A shoe that transforms your wardrobe. To look stylish in a white T-shirt right now, pair it with this nostalgic denim trend. To look stylish in a white T-shirt right now, pair it with this nostalgic denim trend. Jennifer Lawrence's laid-back T-shirt ensemble appears even more stylish due to the return of the denim trend she just showcased. Find it here. The New Year's collection from the brand bodo is chic, sparkling, and stylish with character. The New Year's collection from the brand bodo is chic, sparkling, and stylish with character.

New Year is a time of magic and festivities, and the brand bodo's New Year collection perfectly captures the season's mood, blending fashion trends with a daring spirit. The focus is on three-thread loop knitwear, presented in bright blue, noble gray and basic black, which has become the foundation of the collection. The lineup includes contemporary pieces for stylish boys and girls. Special...

Taylor Swift Recently Rocked the Skirt-and-Boots Ensemble That Shouts '90s Jennifer Aniston.

It's infallible.