Taylor Swift's Best Streetwear Outfits, And How To Recreate Them

Taylor Swift in the Anti-Hero Music video
(Image credit: Republic)

While Taylor Swift’s Eras Tour outfits are sparkly and incredibly colorful, her street style is totally different. Lately, the pop star has been spotted out and about way more than she has in the last few years, meaning we've seen a ton of preppy fall-colored fits that are absolutely iconic. Honestly, it’s a style I desperately want to replicate, and I think there are many in the same position. So, with that in mind, let’s break down some of her most iconic streetwear outfits and how to recreate them. 

Before we get into the specifics of each outfit let's break down the basics that Swift rocks regularly. Along with the statement pieces we're going to talk about, make sure you also have a basic black top, black tights and, of course, red lipstick on hand. With those three essentials, you'll be more than ready to recreate the looks below!

NEW YORK, NEW YORK - DECEMBER 05: Taylor Swift is seen in Manhattan on December 05, 2023 in New York City.

(Image credit: Photo by James Devaney/GC Images)

Taylor Swift Loves A Plaid Longline Jacket, And So Do I  

Lately, Swift has been going for a preppy look that has a bit of dark academia edge. This fit a perfect example of that, and it’s also so fitting for a night out in New York City – which is what the pop star was doing.

In this photo, Taylor Swift is rocking a matching plaid set from Stella McCartney, per taylorswiftstyled on Instagram. She’s also wearing Jimmy Choo x Jean Paul Gaultier wedges and her classic Sheertex tights.

While Stella McCartney is a pricey brand to buy, luckily there are a few other high-quality and slightly cheaper options to recreate the look, like the pieces below:

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$99.99 at Nordstrom

Prince Plaid Double Breasted Coat from Nordstrom for $99.99.

Taylor Swift and Gracie Abrams are seen on November 13, 2023 in New York City.

(Image credit: Photo by DAMEBK/Bauer-Griffin/GC Images)

While Out With Gracie Abrams, Taylor Swift Rocked A Preppy Blazer And White Dress  

During a night out on the town with Gracie Abrams, Taylor Swift wore a gorgeous double-breasted blue blazer by GANT 240 Mulberry Street, Sezane loafer heels and a flowy white dress. Sticking with the preppy vibe, this fit isn’t as dark as the last one, and it has an air of 1989 (Taylor’s Version) to it. 

Both Swift and her Eras Tour opener Gracie Abrams were dressed to impress in their professional looks, and they complimented each other so well. 

If you are looking to recreate the “Cruel Summer” singer’s fit, I got you covered:

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$698 at Nordstrom

Double Breasted Stretch Wool Jacket by Polo Ralph Lauren from Nordstrom for $698.

NEW YORK, NEW YORK - NOVEMBER 04: (L-R Front) Brittany Mahomes, Taylor Swift, Selena Gomez (L-R), Gigi Hadid and Sophie Turner are seen in NoHo on November 04, 2023 in New York City.

(Image credit: Photo by Gotham/GC Images)

Taylor Swift Rocked A Fantastic Miniskirt And Thigh High Boots While Out With The Girls

Lately, Ms. Swift has been spending a lot of time with her gal pals, which include Gigi Hadid, Sophie Turner, Blake Lively and more. On this night in particular, Swift, her bestie Selena Gomez, her newfound friend and fellow WAG Brittany Mahomes and Sophie Turner were seen out for dinner. 

While Gomez was wearing a chic beige sweater dress, and Mahomes was donning a blue jumpsuit, Swift rocked a simple, but effective, black long-sleeve and plaid miniskirt combo. However, the major statement moment of this fit is 100% the thigh-high black boots. Here’s how to recreate it:

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$34.99 at ASOS (USA)

ASOS DESIGN box pleat micro mini skirt in beige plaid for $34.99 at ASOS.

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$39 at Nordstrom

Rib Crewneck Long Sleeve Top by Teasure & Bond from Nordstrom for $39.

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$84.63 at Amazon US

COLETER Women's Leather Knee High Boots Pointy Toe Side-Zip High Heels Dress Boots from Amazon for $84.63.

NEW YORK, NY - OCTOBER 27: Taylor Swift is seen out and about on October 27, 2023 in New York, New York.

(Image credit: Photo by MEGA/GC Images)

This Brown Leather Blazer And Mini Skirt Combo Is Everything

While Swift’s street style tends to include designer pieces, this epic brown look actually features a brand many of us can afford, Madewell, per taylorswiftstyled Instagram. However, everything else in this look is from higher-end stores. That being said, of course, there is a way to recreate this brown look in a more affordable fashion; here’s how:

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$33.12 at Macy's

Women's Plaid Side-Pocket Mini Skirt from Macy's for $33.12.

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$35.98 at Macy's

Women's Fay- Chunky Heel Ankle Boot from Macy's for $35.98.

NEW YORK, NY - OCTOBER 15: Travis Kelce and Taylor Swift are seen leaving the SNL after party on October 15, 2023 in New York, New York.

(Image credit: Photo by MEGA/GC Images)

We All Remember That Legendary Look From The SNL Afterparty 

Travis Kelce and Taylor Swift’s SNL cameo shocked the world, and the internet, specifically Swifties, gushed over the NFL star being a total gent during their date night. However, we also need to take a moment to appreciate the singer’s incredible outfit. 

This was the first time during Swift and Kelce’s relationship that they were seen holding hands in public, and it was a big deal. On top of this being a pop culture moment, it was also an epic fashion event. While the tight end went for a more colorful look, the “Anti-Hero” singer rocked a black corset top, wide-legged black pants, and a plaid trench coat. It was so chic, and it’s a great look to have as part of your closet too.

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$103.20 at Nordstrom

Shinely Plaid & Houndstooth Trench Coat by Steve Madden from Nordstrom for $103.20.

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$50 at ASOS (USA)

adidas Originals Always Original corset top in black from ASOS for $50.

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$47.20 at Nordstrom

Relaxed Waist Wide Leg Trousers by Open Edit from Nordstrom for $47.20.

OCTOBER 12: Taylor Swift watches the Kansas City Chiefs play the Denver Broncos at GEHA Field at Arrowhead Stadium on October 12, 2023 in Kansas City, Missouri.

(Image credit: Photo by Cooper Neill/Getty Images)

Taylor Swift’s Gameday Fits Are Next Level  

Ever since Taylor Swift was seen at her first Chiefs game in September, we’ve also gotten a slew of incredible gameday looks. A personal favorite of mine came when Swift rocked Erin Andrews’ line of NFL gear. While the iconic Chiefs windbreaker isn’t available anymore, there are more options like it. However, if you are looking for something specifically from WEAR, we got you covered – all you need to do is get a cute gameday jacket and pair it with a black top and pants. 

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$59.39 at Amazon US

FOCO Women's NFL Team Logo Ladies Winning Play Windbreaker from Amazon for $59.39.

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$97.49 at Kohl's

Women's WEAR by Erin Andrews Red Kansas City Chiefs Bomber Full-Zip Jacket from Kohl's for $97.49.

As you can see, Taylor Swift has been seriously killing the street-style game recently. From preppy professional looks to iconic gameday fits, she’s been stepping out in style, and I love it. Now, it’s a matter of taking inspiration from these amazing looks and recreating them ourselves while Swift continues to release new projects and absolutely slay the fashion game. 

Riley Utley
Weekend Editor

Riley Utley is the Weekend Editor at CinemaBlend. She has written for national publications as well as daily and alt-weekly newspapers in Spokane, Washington, Syracuse, New York and Charleston, South Carolina. She graduated with her master’s degree in arts journalism and communications from the Newhouse School at Syracuse University. Since joining the CB team she has covered numerous TV shows and movies -- including her personal favorite shows Ted Lasso and The Marvelous Mrs. Maisel. She also has followed and consistently written about everything from Taylor Swift to Fire Country, and she's enjoyed every second of it.

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