Men wore dresses for millennia until the modern era constructed social barriers against doing so. But in recent years, fashion-forward men and socially conscious designers are embracing the idea that clothing has no gender. With the explosion of unisex fashion houses like Telfar and Eckhaus Latta, it is becoming more and more acceptable and accessible for people to wear whatever style suits them best, no matter what gender they identify as. If you are ready to join the wave of Fashion Activists breaking social norms, this guide will help you learn how to choose and style men’s dresses, as well as where to score the best second-hand dresses so you can feel confident in your style.
In today’s society we generally think that dresses are for women. But this was not always the case. When ancient Greeks conquered the pants-wearing Irish, they considered them barbarians because of their restrictive garb. The Greeks still incorporate skirts into men’s military uniforms. In various cultures throughout time, including now, the dress was an entrenched wardrobe piece for men, whether for daily wear or for ceremonial occasions. Several modern-day cultures offer pants alternatives for men from the Arab kaftan to the Indonesdian sarong, the Scottish kilt to the Indian dhoti. So yes, men have worn dresses throughout history and still can today!
Until the 1930s women could only wear dresses and it wasn’t until the 1970s that trousers became accepted for women in professional settings. Women fought hard to be able to wear a pantsuit and now no one blinks an eye at a well-dressed woman in trousers. It’s time for men to take the same control over their sartorial choices and wear whatever pleases them. After all, there are tons of benefits to wearing dresses. As a single-piece outfit, it’s easy to throw on and look put together. There is no mystery about which shirt goes with which pairs of trousers when wearing a dress. Dresses are comfortable and especially so in the hot summer months. Why sweat in traditional men’s attire when you can stay cool and comfy in a breezy dress?
Does it take confidence to be a man in a dress? Sure. But when a man wears a vintage sustainable dress, it means something. It immediately identifies the wearer as a guy that is fashion-forward and not tied to traditional constraints. Someone with a distinctive and strong personality who doesn’t try to blend in or conform.
Ok, ok so men in ancient Greece wore togas but what about walking through downtown in a dress in 2021? It’s actually becoming a glorious time to be alive if you are a man who wants to wear a dress. There are several high-profile dress-wearing pioneers that are showing that a man in a dress is a perfectly acceptable fashion decision.
Most famously, Harry Styles recently graced the December 2020 cover of Vogue wearing a Gucci gown. People lauded him for his bold choice and it was a significant moment for gender-fluid fashion, but he was hardly the first man to step out in a dress.
Brad Pitt was on the cover of Rolling Stone way back in 1999 wearing a glittery miniskirt. No one has ever questioned Pitt’s masculinity so why is this artificial construct even here?
Pharrell Williams explored identity politics in his October 2019 GQ cover wearing a gold couture puffer jacket dress. Known for blurring the gender lines in his clothing, he states “When you listen to yourself and you're comfortable in who you are, you wear what you feel fits and looks right on you. And that's it.”
Jared Leto, Jaden Smith and even Prince William have adopted the dress or skirt as a nonbinary fashion piece. To wear a dress as a man puts you in very good company.
Ready to dip into the fun world of genderless clothing but a bit shy to take the plunge into full dress wearing? A man’s skirt is a more low-key option if a dress feels too avant-garde for now. Breaking down gender boundaries isn’t going to happen overnight, after all.
There two main distinctions when it comes to skirts for men. Kilts are knee-length garments made of woven wool that is most commonly in a tartan pattern. See the Scottish national football team’s official uniform for an example of this look. A good quality kilt can set you back a fair amount since the finest wool can be costly but it’s also a long-lasting fabric. You can shop for a traditional kilt second-hand on Vestiaire Collective if you want a budget-friendly and environmentally-friendly option.
If it’s not a kilt, a skirt can take on almost infinite looks. Rather than the knee-high requirement of a kilt, skirts can be mini, midi or maxi, and come in a variety of fabrics and patterns. A shorter skirt can be paired with leggings or pants so you don’t need to worry about any manspreading.
Several designers have sent men in skirts down the runway including Jean-Paul Gauthier, Vivienne Westwood and even Burberry. Jaden Smith advocated for men in skirts back in 2016 when he wore a skirt from the Louis Vuitton women’s collection. He was a voice for a movement that is finally catching up to his wise understanding that gendered clothing is totally arbitrary.
In the past, men wore trousers as a functional item to ride horses and hunt. Most men aren’t doing that on a daily basis anymore, so there is no actual reason for a man not to wear a dress. A dress is actually more comfortable and utilitarian than a set of trousers.
Billy Porter showed up to the 2019 Academy Awards in a gorgeous velvet tux skirt because his “goal is to be a walking piece of political art.” We don’t think men in skirts should be a revolutionary statement. Fashion has always evolved in line with the social progress of the day, and skirts for men are no different. Gender barriers are eroding, people are asking what masculinity really is, and people want to be able to wear whatever makes them look and feel amazing. If that means a skirt, then more power to you.
Another reason Porter might have chosen to wear a dress is simply to have a more interesting colour palette to choose from. Traditionally, men’s clothes have run a much smaller spectrum than those made for women, so a man looking to stand out doesn’t have a lot of options when shopping for men's styles. Tuxedos and suits have very few variations leading to a homogenizing effect. So what is a man to do who is fashion-forward, edgy, cool, and a little daring? Dresses afford so many more options to make a statement.
But men’s dresses are not just for those wanting to make a splash. The dress is a perfect marriage of form and function, lending itself to daily wear and formal settings. Dresses are comfortable and will keep you cool when the mercury rises. Even if you choose to wear a dress simply because you like how you and feel in it, that’s reason enough.
Men wearing dresses could also be seen as an acknowledgment that while women are able to wear pants nowadays, it carries the implication that menswear is the normative standard and that anything else would be inferior. A man wearing a dress turns that antiquated belief on its head.
Like all fashion choices, there is no easy answer when it comes to what is best. It always comes down to personal style and where you will wear the piece. However, there are a few key dresses that are always going to be welcome additions to any closet.
A monochrome dress is a great staple piece. If you opt for neutral colours like black or tan, you’ll be able to wear this dress on many different occasions and potentially for business settings. But if you want more of an impact, a dress of any hue that you love can be paired with similarly coloured shoes and accessories for a completely monochromatic ensemble.
A summer dress will be your go-to for the hot months ahead. Choosing a dress in natural fabrics like silk or linen will ensure a breathable experience. Organic cotton is a great choice for active men who perspire a lot, as cotton wicks away and absorbs moisture for a cool, dry wear.
If you want to be the centre of attention, you can’t go wrong with a statement dress like a perfect ‘70s dress for all your disco dreams. Or choose any of your favourite decades for a fun way to add glam and personality to your ensemble. When choosing a statement dress, feel free to be you.
Hopefully you are convinced that what you put on your body doesn't matter nearly as much as how it makes you look and feel. Clothing isn’t gendered, attitudes are. Fashion is about taking risks, playing with your creativity, and expressing your unique individuality. If wearing a dress inspires you, then it is an appropriate article of clothing to wear.
The so-called man purse is a great example of a fashion item whose gendered affiliations are blurring. It used to be something of a joke to see a man carrying a purse, but nowadays more and more men are confidently displaying their handbags. Just take a look at Dave Oancea, also known as Vegas Dave, who has a $1.3 million collection of purses, including the world’s most expensive Hermès Birkin bag.
From purses to dresses, modern society is turning away from strictly regimented gendered codes of fashion and superficial gender constraints. By wearing a dress as a man, you’ll be changing the status quo, breaking down artificial barriers and influencing the future of fashion. These are also tenets of the Fashion Activist. At Vestiaire we champion anyone who is willing to stand by their beliefs proudly. That includes people whose beliefs are to change the face of fashion to make it a more sustainable industry. Our global community of nine million members and counting choose to shop second-hand as a challenge to the status quo of fast fashion and over consumerism. From dresses for men to vintage wedding dresses, we make it easy to find pre-loved fashion that you love, in a way that is sustainable for the planet. If you are a man ready to take control of your fashion choices by including a dress into your wardrobe, head to Vestiaire Collective to browse our selection of pre-loved dresses. It’s a whole new world.