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  • Writer's pictureNeha Ogale

A New Era of Women in Menswear Is Here

It’s simple: we’re becoming the men we wanted.


L-R: Charlotte Rampling (1975), Naty Abascal (1967), Samantha Jones (1975)

Lately, I’ve had a fondness for loafers and a keen eye for lost causes.  

I know veering from heels toward flats isn’t profound. Neither is the perennial urge to swear off men (more on that later). It’s worth noting, though, how women’s fashion has changed considerably over the past 40 years. The 1990s in particular heralded a major turning point in the industry, shedding the pomp and froufrou of the ’80s to reveal a sleeker, more minimalistic look canonized by fashion icons like Princess Diana and Carolyn Bessette-Kennedy. 

Though trends ebb and flow, changes in the tides of fashion have often reflected the sociocultural and political climate of the era. The evolution of women’s fashion is on my mind because of another remarkable shift I’ve been witnessing post-pandemic. I can’t help but notice how the garb of this current fashion epoch is riding the coattails of fourth-wave feminism. 

In a turbulent world where more and more women are electing to delay marriage and childrearing — with many more choosing the single, child-free life — changes in women’s fashion have followed suit, especially in the form of menswear-inspired styles engulfing the market. We’ve banished the chevron peplum tops, skin-tight jeggings, and loud geometric jewelry that practically defined the 2010s. The end of an era, thank goodness. Now, we don oversized blazers (like this one famously worn by Lady Di), crisp Oxford shirts à la Bessette-Kennedy, understated jewelry, and sleek leather footwear. 

It’s no surprise we turn to the past for menswear inspiration. The late '90s was an era of tremendous social upheaval that fueled a hunger for personality; Princess Diana and Carolyn Bessette-Kennedy were iconic because their celebrity and street style made closet basics look elevated, accessible, and more importantly, so damn good. Modern silhouettes and textures inspired by these women serve as a timely reminder that some things just never go out of style. Major retailers like Everlane, Madewell, and Banana Republic are just a few brands that have embraced, updated, and perfected this look, curating ultra-polished style edits with pieces like ’80s inspired blazers and wide-legged trousers

L-R: Carolyn Bessette-Kennedy (1995), Bianca Jagger (1979), Princess Diana (1989)

Much of today’s androgynous clothing is a modern take on closet staples that have been around for ages, at least for men. Women began experimenting with more masculine styles during the Victorian era, with the introduction of bloomers in the mid-19th century. Pantaloon-like garb subsequently became a statement of defiance among early women’s rights activists like Lucy Stone and Elizabeth Cady Stanton. These acts weren’t greeted with impunity. Abolitionist and Civil War surgeon Mary Edwards Walker endured multiple arrests between 1866 and 1913 for dressing like a man (here she is decked out in what appears to be a three-piece suit.) 

Trousers became more acceptable during World War I as women began entering the workforce, though this was a matter of practicality rather than social progress. Not until the Interwar Period did slacks really make a breakthrough, thanks to celebrities like Marlene Dietrich and Katharine Hepburn, who were frequently photographed in menswear. But these styles weren’t considered truly fashionable until after World War II, when for the first time we witnessed the mass production and availability of tailored pants, crisp shirts, and other traditionally masculine attire on the market for women. 

Superficially, the trend of menswear-inspired pieces like tailored button-downs and quarter zips that drape just-so is a great thing. I favor a more androgynous aesthetic, with my feathered shag haircut and boyish figure. There’s a casual elegance to the menswear look that oozes sophistication and a je ne sais quoi appeal. There’s a stylistic savviness, too. Pieces like structured shirts and high-waisted trousers will always be utilitarian in their timelessness, comfort, and customizability. The right pairings can be professional or informal, befitting the office or a casual lunch. 

The proliferation of menswear for women holds symbolic significance as well. The androgyny and clean lines of contemporary women’s fashions embody many of the feminist values of our time like independence and assertiveness — just as the sleeker postwar looks foreshadowed the rise of the women’s liberation movement two decades later. These styles are also the sartorial reflection of qualities we have been socialized to associate with masculinity: self-assurance, steadfastness, strength of character. They are, in both aesthetic and essence, antithetical to the inconsistent, unreliable suitors flitting in and out of our lives at their whimsy.

Bottega Veneta FW24

Just ask any woman in the trenches — I mean, on the market. Most would say the dating pool more closely resembles a bog, with its waters muddied by irreverent, poorly-dressed, under-educated, and flighty characters. From what I'm told, your average date has all the intent and vitality of a pair of polyblend pants plucked off the clearance rack at Zara. But hey, at least the pants won’t stow away in other people’s dressers behind your back. And they’ll definitely last longer than he will.

Choosing a romantic companion is as much of an investment as a high-quality coat. Over time, the coat will reveal flaws — maybe a loose stitch or a minor stain — but it’s nothing a lint brush and a quick trip to the dry cleaners couldn’t fix. It’ll still keep you warm. The shortcomings of boyfriends and husbands are much less predictable and much more damaging. 

No wonder so many of us are opting for solitude — and what an auspicious time it is to be alone. Even with reproductive rights under virtual siege, women enjoy more freedoms now than at virtually any other point in history. We’re among the most educated members of society and make up a significant part of the workforce. We own credit cards and property and businesses. We’re free to do what we like, say what we like, and wear what we like. 

But the price of freedom has been costly. Independence and disinterest in being cared for are not the same thing, yet the two have somehow grown to conflate. We don’t need men to hold open doors for us, so they don’t. We can buy ourselves flowers, so they don’t. We look after ourselves, so they don’t. The irony is, for all our autonomy, it can often feel like we’re in perpetual servitude to the male ego — as if it’s a repository in constant pursuit of physical and mental fulfillment without any genuine reciprocity of those efforts — only to be discarded when our emotional coffers inevitably run dry. Transaction complete.   

Words of wisdom from perennial menswear icon Miranda Hobbes (2004)

Thankfully, we can choose different men and different clothes. Wearing pants is certainly not a political statement anymore; when we shrug into a blazer or slip on a pair of brogues, we aren’t giving the finger to the establishment. But these clothes are an expression of something that transcends daily routine: they’re a sartorial suit of armor that lends us the security and resolve of which so many of us have been deprived, redefining masculinity and its ideals with a stylish fervor in the process. 

It’s simple. We’re becoming the men we wanted. 

L-R: Fanni Boström (2007), Fran Leibowitz (1979), Bianca Jagger (1978)

The menswear-inspired style of dress is almost a form of escapism. Clad in a waistcoat or tapered trousers, you don’t have to be you. Well, you’re still you; but you could be the premium, ad-free, 4K restoration version. You could be a clean-cut hedge fund manager (if you’d gone to business school), or the aristocratic heir to a sprawling estate (if you’d come from nobility). It’s a charming fantasy borne of a reality where so much online chatter is focused on becoming our best selves; self-improvement seems to be the rallying cry for influencers, the girlbosses, the ones with the “5 to 9 before my 9 to 5” routines. Never mind that this kind of do-and-be-better content for male audiences is manifestly absent. But I digress. 

As we approach the halfway mark of the 2020s, I wonder how women’s fashion and sense of identity will evolve over the next decade. Which trends and feminist ideas will endure while others fade into memory? Only time will tell. Until then, I hope he texts you back. 🌀


Neha Ogale is a twenty-something freelance writer, recovering coat hoarder, and indie film enthusiast based in NYC. You can find her on Twitter @urbangremlin.


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