Throughout the '90s and early ‘00s, baggy clothing reigned supreme.
While tiny miniskirts paired with bedazzled bikini tops and low-rise skinny jeans were also at the forefront of fashion, it was JNCO jeans and XXL t-shirts that truly captured the sartorial imagination of the new millennium teen.
Yet the popularity of masculine, supposedly ill-fitting and loose clothing throughout the late 20th and early 21st century was simply a resurgence of a “Borrowed from the Boys” style which originated following the Second World War.
As women across the globe donned boiler suits and bandannas to fill in for male factory workers during the war effort, a sartorial shift occurred through which women took the opportunity to wear practical, previously forbidden items of clothing like trousers and pantsuits.
The rumblings of a trend towards boyish fashion, however, were already in the works thanks to tomboy style icons such as Katherine Hepburn – who favoured wide-leg trousers, cashmere sweaters worn beneath blazers and leather moccasins. But the post-war fashion shift cemented it. Marilyn Monroe, for instance, was known to wear her boyfriend’s jeans on set, while Jane Birkin later pioneered a cropped pixie cut paired with men’s vest tops and ripped jeans.
The concept that wearing masculine clothing doesn’t necessarily mask one’s femininity but can often work to emphasise it - with a side-serving of boyish charm - was spearheaded by these fashion-forward women throughout the decades.
Louis Botto writes in an April 1975 print edition of The New York Times, “In Manhattan, on a Madison Avenue bus queue, one spots nine women wearing trousers; four of them also have on suede and leather outerwear of the kind once worn only by lumberjacks and bowling captains. One woman, beyond redemption, wears men's work shoes.”
Despite decades of undulating popularity, it seems as though “Borrowed from the Boys” fashion still shocks certain onlookers. Nevertheless, the latest homme/femme trend to take the fashion world by storm is that of unisex boxer shorts worn not as underwear, but as a pair of casual lounge shorts.
Style variations are surprisingly wide-ranging, with some choosing to pair their boxer shorts with feminine prairie-style shirts complete with oversized lace collars. A select few will don a matching, oversized striped lounge shirt with a pair of chunky loafers, while others might opt for a Princess Diana-inspired look with a baggy collegiate jumper and some Birkenstock Clogs.
When it comes to the accompanying beauty choices, boxer short enthusiasts will likely opt for a barely touched, just-got-out-of-bed hairstyle and a no-makeup, makeup look.
If we’ve convinced you to hop on the tomboy train, keep scrolling for an edit of the best men’s style boxer shorts for women available to shop now.
See below
Best clogs for women, the unlikely winter favourite that works all year round
Best knitted jumpers for women to complete your autumnal look
Best suits for women that are in style this season
Best dungarees for women for comfortable style in denim and other materials
Pink Striped Classic Unisex Boxers
Embodying the style of the UK’s southern coast, Speltham’s ethically handmade unisex loungewear pieces make us dream of reading books on a breezy, sandy beach with an iced coffee and a warm fleece in tow.
Buy now £29.95, Speltham
Sporty & Rich Oxford Striped Cotton Shorts
A classic pair of cotton poplin shorts featuring breezy split hems, this time with a nostalgic, 90s-esque elasticated waistband bearing the name of the Instagram-favourite brand. We’re big fans of the turquoise-hued Oxford stripes and would pair these boxers with an oversized raglan t-shirt
Buy now £85.00, Selfridges
Lilyáurea Undyed Silk Boxer
Specialists in silky smooth clothing that feels as light on the skin as a delicately running stream of water, these 100 per cent silk boxer shorts are the epitome of luxury. Dyed with all-natural dyes, the bright lemon-yellow colourway would look brilliant alongside some chunky black loafers with yellow-gold buckles and a sumptuously soft white silk shirt.
Buy now £49.00, Lilysilk
Tekla Coffee Shorts
Connoisseurs of Scandinavian aesthetics, Tekla know a thing or two about combining comfort with unadulterated style. Though available in a variety of colourways, both striped and plain, the rich coffee colour of these boxer shorts immediately caught our attention. Unlike traditional boxer shorts, these have been purposefully designed to be worn exposed and have the elasticated, drawstring waistband to prove it. Pair with the matching long-sleeve or short-sleeve shirt depending on the season.
Buy now £88.00, Sugar
Uniqlo Checked Woven Boxers
You might have noticed that these boxer shorts are far cheaper than the majority of styles we’ve listed thus far. This is because these shorts are not a feminine recreation of boys’ boxers, but simply a pair of men’s underwear. Perfect for ‘90s grunge-inspired outfits, we’re nevertheless obliged to warn you that these shorts will likely bunch up and crease when worn out on the town.
Buy now £7.90, Uniqlo
LMND Chiara mid-rise regular-fit cotton shorts
Offering a flattering mid-rise fit, these delightful green cotton shorts by LMND feature two practical slip pockets hidden towards the front of the garment.
Buy now £125.00, Selfridges
Self Portrait crystal-embellished mid-rise woven shorts
A boyish, boxer short style made suitable for a night out? Sign us up. These crystal-embellished mid-rise shorts from Self Portrait are sure to brighten up your wardrobe in an instant.
Buy now £260.00, Self Portrait
Ami Alexandre Mattiussi White Ami de Cœur Boxers
That iconic Ace of Hearts embroidered logo has captured the hearts of sartorial enthusiasts across the globe, so we couldn’t help but include a pair of bright white cotton boxer shorts from Ami Paris in this edit.
Buy now £55.00, Ami Paris
Red Gingham Printed Boxer
Part of the brand’s ‘Teenage Fiction’ collection, wear these 100 per cent cotton red gingham boxers from Jaded London under a pair of baggy jeans which sit low enough to display the big, bold ‘American Dream’ print on emblazoned on the front.
Buy now £25.00, Jaded London
