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How to Wear Bermuda Shorts With Boots

Spotted at Fashion Week: A New Hack For Making Shorts Look Superchic

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From shirt jackets to baseball hats and belts galore, New York Fashion Week has given us a lot of street style trends to inspire new and innovative outfits. One look we didn't anticipate being inspired by in February? Bermuda shorts! Specifically, Bermuda shorts paired with tall boots for a cold-weather take on the Spring trend. Sound crazy? Stick with us, it's actually quite good.

After dissecting the Spring/Summer 2020 collections and deducing from them the biggest trends, we quickly realised that Bermuda shorts were going to be big in 2020. While Bermuda shorts started percolating on the trend circuit by way of denim and biker shorts earlier in 2019, the new-decade's Bermudas come more tailored and polished, including trouser-like silhouettes and supple leather styles. While we've had this trend on the back-burner to wear with Spring's biggest shoe trends like minimal sandals and loafers, the NYFW street-style scene proved to us that we need to start busting them out now with tall boots — from to-the-knee styles to thigh-high shapes. The result of this power pairing is refreshingly chic and, likely, a combo you haven't experimented with.

Even better, while this fresh Bermuda-short-and-tall-boot formula is perfect in cool weather, it's totally transitional as we inch our way closer to Spring temperatures. The knee-high boot trend is showing no signs of slowing down, thus making this unique combo one that makes the otherwise cold-weather shoe style suitable in balmier weather.

To give you a visual how-to on styling Bermuda shorts with tall boots, ahead I've culled my favourite outfits from NYFW. When (not if!) you become convinced to try the look for yourself, I've picked out an edit of stylish shorts and boots at a range of price points so you can re-create these looks ASAP.

Image Source: Style Du Monde

How to Wear Bermuda Shorts With Boots

Black leather Bermuda shorts and tall boots á la Kendall Jenner put a fresh spin on head-to-toe black.

Pixie Market Riley Leather Culottes

Pixie Market Riley Leather Culottes ($118)

Image Source: pixiemarket.com
Pixie Market Riley Leather Culottes
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Stuart Weitzman The Milla 60 Boot

Stuart Weitzman The Milla 60 Boot ($398, originally $795)

Image Source: stuartweitzman.com
Stuart Weitzman The Milla 60 Boot
$398
from stuartweitzman.com
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How to Wear Bermuda Shorts With Boots

A monochromatic palette makes teaming a pair of leather Bermuda shorts and knee-high leather boots a little easier. For a playful pop, a neon bag is the perfect accent.

Image Source: Style Du Monde

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Frankie Shop Flat Front Leather Shorts

Frankie Shop Flat Front Leather Shorts ($118, originally $169)

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Sam Edelman Raakel Block Heel Tall Boots Shoes

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Image Source: bloomingdales.com
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How to Wear Bermuda Shorts With Boots

A leather pair of over-the-knee boots make a tailored pair of khaki Bermuda shorts feel edgy as ever.

Image Source: Style Du Monde

& Other Stories High Waisted Belted Cotton Shorts

& Other Stories High Waisted Belted Cotton Shorts ($79)

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Steve Madden Terrain Black Leather Boots ($231)

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How to Wear Bermuda Shorts With Boots

Make a black turtleneck and boots more exciting with a tailored pair of leather Bermuda shorts in an Earthy green shade.

Aeron- Moss Helen Wide Leg Capri Pants

Aeron- Moss Helen Wide Leg Capri Pants ($408)

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Tamara Mellon x Frame PIC Over The Knee Boots

Tamara Mellon x Frame PIC Over the Knee Boots ($895)

Image Source: tamaramellon.com
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How to Wear Bermuda Shorts With Boots

Obsessed with neutrals? How about black leather Bermuda shorts, Earthy green boots, a black turtleneck, and a cream or tan jacket.

Babaton Serif Long Wide-Leg Short

Babaton Serif Long Wide-Leg Short ($128)

Image Source: aritzia.com
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Dear Frances Sleeve Boot

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How to Wear Bermuda Shorts With Boots

Denim Bermuda shorts aren't just for warm weather! Right now, try them with colourful snake-print boots and a chunky cardigan.

FRAME Le Vintage Bermuda Sanded Seam Raw Edge

FRAME Le Vintage Bermuda Sanded Seam Raw Edge ($200)

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Paris Texas Python-Print Stiletto Knee Boots

Paris Texas Python-Print Stiletto Knee Boots ($825)

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How to Wear Bermuda Shorts With Boots

A Bermuda short suit set with snake-print boots is a sophisticated way to rock the trend.

Image Source: Style Du Monde

Frankie Shop Julie Pleated Gabardine Shorts

Frankie Shop Julie Pleated Gabardine Shorts ($125)

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Kenneth Cole Justin Snake Print High Heel Knee Boot

Kenneth Cole Justin Snake Print High Heel Knee Boot ($110, originally $225)

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How to Wear Bermuda Shorts With Boots

Experiment with textures and pair black leather Bermuda shorts with suede over-the-knee boots.

Self-Portrait Faux-Leather Bermuda Shorts

Self-Portrait Faux-Leather Bermuda Shorts ($310)

Image Source: mytheresa.com
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Jessica Simpson Ladee Over the Knee Boot

Jessica Simpson Ladee Over the Knee Boot ($90, originally $150)

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How to Wear Bermuda Shorts With Boots

Whether tucked in or worn loose over tall suede boots (mine are a vintage Gucci pair from Vestiaire Collective!), plaid Bermuda shorts are the perfect way to try this outfit formula at work.

Image Source: Style Du Monde

H&M Wide-Cut Shorts

H&M Wide-Cut Shorts ($60)

Image Source: www2.hm.com
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Gucci Black Suede Boots

Gucci Black Suede Boots ($290, originally $359)

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How to Wear Bermuda Shorts With Boots

According to fashion girls at New York Fashion Week, there's no such thing as too much leather. So, why not team a pair of black Bermudas in the luxe fabric with a croc-effect pair of leather boots.

Frankie Shop Pernille Pleated Faux Leather Shorts

Frankie Shop Pernille Pleated Faux Leather Shorts ($119)

Image Source: Net-a-Porter.com
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Schutz Pedria Boot

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Image Source: schutz-shoes.com
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How to Wear Bermuda Shorts With Boots

Who said black and brown don't go together never saw this genius Bermuda-short-and-tall-boot outfit.

Image Source: Style Du Monde

COS Straight Leather Shorts

COS Straight Leather Shorts ($350)

Image Source: cosstores.com
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How to Wear Bermuda Shorts With Boots

Edge up leather Bermuda shorts with an on-trend pair of "ugly" lug-sole boots.

Image Source: Style Du Monde

Pull&Bear Shorts

Pull&Bear Shorts ($36)

Image Source: pullandbear.com
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