Name a more iconic duo than boots and blue jeans.
Struggling to think? We don’t blame you. It’s a near-impossible task. Finely crafted leather soles and dreamy denim have more chemistry than Bonnie and Clyde. Not to mention a more storied history filled with history-making moments from Marilyn Monroe’s white button-up and denim pairing to Princess Diana’s blazer and jeans combo from 1988.
There’s a certain timelessness that comes with shimmying into your favourite pair of jeans and slipping your feet into a great boot. You are quite literally walking in the footsteps of fashionistas who have come before. A young Winona Ryder, Cher, Bruce Springsteen and Debbie Harry come to mind - and that’s not even scratching the surface.
Despite the ongoing romance between boots and jeans, they can pose a problem for novice fashion followers. The issue of styling rears its head time and time again, simply because the type of jeans you wear dictates the style of boot to team them with and vice versa.
For example, knee-high boots can cause rucking of the jean and tightness around the leg. They are better suited to a Nineties denim skirt or retro jorts due to their elongated stature. This prompts many shoppers to switch to shorter silhouettes such as Chelsea boots or cropped kitten heels. Yet, Noughties-fearing consumers will know that by doing so, they run the risk of looking ‘cheugy’.
The term, which disapprovingly refers to all things passé in the trend department, is a worst-case scenario. How to avoid this, well, that is the question.
Thankfully, we have many sources of inspiration to help banish our boot-based woes. Poster girls including Alexa Chung, Elsa Hosk and the Haim sisters frequently take to social media to document their boot-jean ensembles. Whether opting for a buckled Miu Miu moment or a classic pointed Western, influencers are proving that there are ample ways to style boots and jeans to perfection.
High fashion houses are also lending a hand. Rabanne, Coperni, Blumarine and Diesel all sent denim-clad models in boots down the runway in recent seasons. Point-toe-heeled boots and bulbous flatforms were particularly popular, marking a revival of grunge Nineties sentiment and Y2K themes.
Less trend-led designs materialise in the form of Doc Martens and Timberlands. Workwear-themed shoes have prevailed over the fickle trend cycles, establishing themselves as failsafe timepieces. For those who are partial to a slice of punk attitude or androgyny, this is the best place to start.
Whether pining after a Y2K marriage of raw-hem flares and kitten heels or looking to invest in some statement stompers to see you through the year, look no further. Discover the best boots to pair with jeans and shop our edit below.
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Sandro Helen Ankle Boots
A glint of a buckle goes a long way. Sandro’s cool-girl boots are crafted from ebony black leather and exude Parisian chic. Say goodbye to bad boots and bonjour to your new everyday stompers.
Buy now £257.40, Selfridges
Bimba Y Lola Black Leather Heeled Gaucho Boot
Bimba Y Lola’s Heeled Gaucho Boot is ideal for those wanting a blend of kitten heel kitsch and timeless leather structure. The boots, which are a grand 60 per cent off, would slip seamlessly under a pair of straight-leg jeans. Pair yours with a cashmere knit and pinstripe blazer.
Buy now £156.00, Bimba Y Lola
Mango Leather Cowboy Ankle Boot
Mango is the first port of call for consumers wanting to spend less. The high street hero offers an array of easy-wear shoes, and these Western ankle numbers are simply made for jeans. Featuring eye-catching seam detailing and a pointed toe, Mango’s cowboy boots promise effortless year-round wear.
Buy now £59.99, Mango
Jil Sander Leather Chelsea Boots
For those who prefer a less feminine silhouette, look to Jil Sander. The brand oozes cool, as shown in its subverted Chelsea boot design. Rounded, exaggerated soles that feature unexpected proportions are fused with traditional elasticated inserts and heel tabs, making for a modern take on the retro design.
Buy now £950.00, Farfetch
Isabel Marant Duerto Cutout Suede Knee-high Boots
Who said cowboy boots were just for summer? Isabel Marant’s beautifully made Western boots will complement any monochrome outfit with ease. Note the Cuban heels and floral topstitched motifs that pepper the shoes with intrigue.
Buy now £795.00, Net-A-Porter
Vagabond Vivian Boots
Go hell for leather with Vagabond’s racy red leather boots coined the Vivian. The shoes adopt a sassy pointed heel, an easy-wear zip-fastening, block heels and decorative seams. Wear yours with baggy blue jeans for a sophisticated yet effortless aesthetic.
Buy now £165.00, Vagabond
Charles and Keith Metallic Buckled Ankle Boots
Biker boots are flying off the shelves and selling like hotcakes. Charles and Keith’s Metallic Buckled Ankle Boots are a unique take on more orthodox, Miu Miu-derived designs. Grunge buckle detailing perches on the side of the shoe, which is completed with a space-age silver finish. Put on some baggy wide-legs and let the It-girl shoes coolly peek out from underneath.
Buy now £119.00, Charles and Keith
Diesel D-Eclipse Logo Plaque Boots
Complete your Charlie’s Angels aesthetic with Diesel's sassy slip-ons which feature the brand’s Y2K logo plaque and a sharp point-toe. With a patent finish and a slim high heel, it is no surprise that these boots have flown off the shelves since stepping off the runway.
Buy now £495.00, Farfetch
Topshop Honey Premium Leather Block Heel Ankle Boot
While it is no longer with us in person, Topshop is still with us in spirit and via ASOS. The brand never sleeps on cute boots for all ages, and these snakeskin shoes with a smart square toe are an affordable, uber-wearable pick.
Buy now £85.00, ASOS
Miista Sander Brown Boots
It’s a basic fact that all the It-girls are wearing Miista. The shoewear label has gained a cult following among various fashion circles, thanks to its flair for Nineties styles and uniquely dyed leather exteriors. The Sander boots are firmly on our wishlist and would look flawless teamed with some raw-hem straight legs.
Buy now £430.00, Miista
Toteme + NET SUSTAIN The Slim Leather Ankle Boots
If you’re looking to invest, look to Toteme. The brand’s Slim Leather Ankle Boots adopt a streamlined style with a patent croc effect, meaning they never run the risk of becoming cheugy. Add them to your wardrobe rotation and enjoy them for years to come.
Buy now £600.00, Net-A-Porter
Ganni Paneled Leather Chelsea boots
Ganni’s wildly popular design has gripped swathes of trend-obsessed twenty-something-year-olds, no doubt due to the shoes’ buttery leather exterior, rounded toe and chunky lug soles. Slip into some casual jeans and slide these timeless boots on for an easy sartorial win.
Buy now £345.00, Net-A-Porter
& Other Stories Thin Heel Leather Boots
Boots typically don’t come cheap, but nothing about these affordable & Other Stories looks inexpensive. A fine black leather constructor is elevated by a striking heel square-shaped toebox.
Buy now £59.00, & Other Stories
Maison Margiela Tabi Boots
Margiela's Tabi Boots are arguably one of the most iconic boots created. The split-toe shoes first debuted at the brand's very first runway show in 1989 and have been a best-seller ever since. They boast supple ebony leather, an ankle design and a chunky cylindrical heel.
Buy now £990.00, Net-A-Porter
Loewe Toy Paneled Leather Ankle Boots
Carefully style these leather ankle boots over your baggiest pair of dark wash jeans for a fashion editor aesthetic. Adopting Loewe’s house motifs such as quirky boot silhouettes and unconventional heel structures, these ankle boots are designed to mimic slouch pants with petal-shaped toes and lacquered toy heels.
Buy now £1650.00, Net-A-Porter
Dr Martens Sinclair Milled Nappa Leather Platform Boots
Be warned: you must break in your Dr Martens before prolonged wear. Take it from our personal experience, wearing a new pair of these shoes is a recipe for disaster and your feet will not thank you. Opt for these shoes in advance of your summer schedule and wear them in thoroughly. Once you’ve done so, they’ll be some of the most comfortable you’ll own - but it does take a few packets of Compeed to get there.
Buy now £189.00, Dr Martens
Gucci Women’ Snow Boot
Hear us out. Yeti boots are here to stay, taking their place on the radar of fashion darlings from Mia Regan to Dua Lipa. These lavish Gucci options are true head-turners, but brands such as Monki and Debenhams stock more affordable options for those on a budget. Apple bottom jeans at the ready.
Buy now £1410.00, MyTheresa
Stradivarius Embroidered Cowboy Ankle Boots
Tuck in your jeans or let them roam free over these vintage-inspired cowboy boots. Available in several colours to choose from and featuring easy-wear pull tabs, these inexpensive Westerns are ready for a rodeo.
Buy now £39.99, Stradivarius
