From shirt jackets [1] to baseball hats [2] and belts [3] galore, New York Fashion Week has given us a lot of street style trends [4] 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 [5] and deducing from them the biggest trends, we quickly realised that Bermuda shorts [6] 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 [7] like minimal sandals and loafers [8], 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 [9] 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.
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 [11] ($118)
Stuart Weitzman The Milla 60 Boot
Stuart Weitzman The Milla 60 Boot [12] ($398, originally $795)
How to Wear Bermuda Shorts With Boots
A monochromatic [13] 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.
Frankie Shop Flat Front Leather Shorts
Frankie Shop Flat Front Leather Shorts [14] ($118, originally $169)
Sam Edelman Raakel Block Heel Tall Boots Shoes
Sam Edelman Raakel Block Heel Tall Boots Shoes [15] ($158, originally $225)
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.
& Other Stories High Waisted Belted Cotton Shorts
& Other Stories High Waisted Belted Cotton Shorts [16] ($79)
Steve Madden Terrain Black Leather Boots
Steve Madden Terrain Black Leather Boots [17] ($231)
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 [18] ($408)
Tamara Mellon x Frame PIC Over The Knee Boots
Tamara Mellon x Frame PIC Over the Knee Boots [19] ($895)
How to Wear Bermuda Shorts With Boots
Obsessed with neutrals [20]? 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 [21] ($128)
Dear Frances Sleeve Boot
Dear Frances Sleeve Boot [22] ($795)
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 [23] ($200)
Paris Texas Python-Print Stiletto Knee Boots
Paris Texas Python-Print Stiletto Knee Boots [24] ($825)
How to Wear Bermuda Shorts With Boots
A Bermuda short suit set with snake-print boots is a sophisticated way to rock the trend.
Frankie Shop Julie Pleated Gabardine Shorts
Frankie Shop Julie Pleated Gabardine Shorts [25] ($125)
Kenneth Cole Justin Snake Print High Heel Knee Boot
Kenneth Cole Justin Snake Print High Heel Knee Boot [26] ($110, originally $225)
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 [27] ($310)
Jessica Simpson Ladee Over the Knee Boot
Jessica Simpson Ladee Over the Knee Boot [28] ($90, originally $150)
How to Wear Bermuda Shorts With Boots
Whether tucked in or worn loose over tall suede boots (mine are a vintage Gucci [29] pair from Vestiaire Collective [30]!), plaid Bermuda shorts are the perfect way to try this outfit formula at work.
H&M Wide-Cut Shorts
H&M Wide-Cut Shorts [31] ($60)
Gucci Black Suede Boots
Gucci Black Suede Boots [32] ($290, originally $359)
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 [33] ($119)
Schutz Pedria Boot
Schutz Pedria Boot [34] ($325)
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.
COS Straight Leather Shorts
COS Straight Leather Shorts [35] ($350)
Dolce Vita Kasidy Boots
Dolce Vita Kasidy Boots [36] ($161, originally $242)
How to Wear Bermuda Shorts With Boots
Edge up leather Bermuda shorts with an on-trend pair of "ugly" [37] lug-sole boots.
Pull&Bear Shorts
Pull&Bear Shorts [38] ($36)
Asos Designs Capital Chunky Knee High Boots
Asos Designs Capital Chunky Knee High Boots [39] ($80)