Men’s boxer shorts are a staple in most guys wardrobes, but their history is more fascinating than you might think. From their beginnings as practical sportswear to becoming a stylish statement, boxer shorts have evolved over the decades to reflect changes in society, culture, and fashion.
Here’s a quick dive into their story.
1. The Birth of Boxer Shorts (1920s-1930s)
Boxer shorts as we know them were born in the 1920s, thanks to Jacob Golomb, founder of the sportswear brand Everlast. Golomb designed them for boxers, replacing the restrictive leather-belted trunks with a new innovation: elastic waistbands.
This simple change made them more comfortable and functional for athletes. The name “boxer shorts” stuck, and they quickly became synonymous with freedom of movement. Possibly not the best workout underwear but we have to assume that a boxer would be wearing some sort of groin protection/support under the boxer short.
2. WWII and the Mainstream Adoption of Boxers (1940s)
During World War II, boxer shorts became standard issue for soldiers, solidifying their role as everyday underwear. When soldiers returned home, boxers transitioned into civilian life, and their popularity soared.
They became a practical and comfortable choice for men, favored for their loose fit and breathability. You can still buy WWII issue boxer shorts today on markets like Etsy.
3. The Briefs Challenge (1950s-1970s)
The post-war years saw a new contender in the men’s underwear market: briefs. Thanks to their snug fit and modern appeal, briefs took over as the dominant style for much of the mid-20th century.
Boxer shorts remained in the background, favored by traditionalists but largely overshadowed in pop culture. Yet, they held onto their loyal fanbase, especially among men who valued their classic, roomy design – such as the dude in glasses in this picture, who actually looks a little envious of the guy in the yellow tanga….
4. Men’s Boxer Shorts Reinvented (1980s-1990s)
The 1980s marked a turning point for boxer shorts. They came back into the spotlight as a symbol of style and sophistication, spurred by innovative branding and design.
- Calvin Klein’s influence: In the US, Calvin Klein ads featuring celebrities and supermodels wearing boxers sparked a cultural phenomenon. Suddenly, boxers weren’t just underwear—they were a fashion statement. Calvin Klein now sells a very limited range of Boxer shorts directly but has more choices available through other retailers.
- Paul Smith’s impact in the UK:
Designer Paul Smith redefined boxers as stylish and luxurious. He introduced vibrant patterns, bold stripes, and playful designs that appealed to a younger, trendier audience.- Smith used high-quality fabrics, turning boxers into a premium product.
- By featuring boxers in his high-end stores, he elevated them from mere utility to a symbol of modern British style.
- His designs resonated with men who wanted their undergarments to reflect personality and sophistication.
This dual influence—Calvin Klein in the US and Paul Smith in the UK—helped boxer shorts reclaim their place as a must-have item in men’s wardrobes. Like Calvin Klein, Paul Smith is all about the boxer brief today but you can still buy the classic Signature Stripe boxer short which is an absolute classic,
5. The Boxer Brief Era (2000s-Present)
In the 2000s, boxer briefs emerged as a hybrid option, combining the snug fit of briefs with the longer cut of boxers. Despite this shift, traditional boxers retained their charm, especially among men who valued comfort and breathability.
Modern boxer shorts now cater to a wide range of tastes, from classic white cotton to designer prints. Brands continue to innovate with materials, patterns, and fits, keeping boxers relevant in an ever-changing market.
6. Men’s Boxer Shorts Today: Style and Symbolism
Today, boxer shorts are more than just underwear—they’re a cultural icon. They’ve been featured in movies, music videos, and fashion shows, representing everything from relaxed masculinity to bold self-expression.
From plain and practical to stylish and statement-making, boxer shorts remain a symbol of comfort and individuality. Plus, if you choose carefully, they are damn sexy.
Why It Matters
The history of boxer shorts isn’t just about underwear; it’s a story of innovation, cultural shifts, and personal expression. Whether you’re a fan of classic designs or bold patterns, boxers continue to make their mark on men’s fashion—and they’re not going anywhere anytime soon.
