As it turns out, raiding your children’s or grandchildren’s closet might not be such a bad thing.

Believe it or not, boomers can wear some of the trends found in the wardrobes of millennials without being branded mutton-dressed-as-lamb.

Track pants, hoodies, jeans, sneakers and leggings are just some of the items pilfered from today’s youth and can be found working their way into the wardrobes of an older generation. Not unlike this style editorial, which features a group of professional women working in various aspects of the fashion industry. Wearing clothes from their own wardrobes, their unique sense of style has embraced a few of these items – for many years, in some cases – for a look that has a youthful vibe but is, more importantly, age appropriate.

While some male industry titans embraced dressing down – such as the late Steve Jobs did in his black turtlenecks and jeans – working women were rarely allowed the latitude to assume this relaxed mode – just ask Hillary Clinton and her pantsuits. But overall, there has been a shift in what’s considered appropriate, not just for age, but also in the public sphere and the office. It’s the casualization of style.

Naturally, this trend will be interpreted entirely different by boomers and millennials – mostly by choice of brands and how they are worn. While today’s fashion-obsessed teen might covet a track pant from Rihanna’s red-hot streetwear label, Fenty Puma, an older person might seek the old-school appeal of a classic three-stripe Adidas track pants.

Of course, none of these items are unfamiliar to boomers, who might have worn any number of them back in their younger days, just not for pulled-together occasions. Right now, they just happen to be trending in fashion with millennials. And considering that they are one of the largest demographic groups – some 80 million in America alone – favoured by marketers, retailers, designers and other industries, what’s on their radar will unavoidably influence fashion.

This is not the first time the youth sector of society has pushed fashion forward. With the opening of the Yves Saint Laurent Museum in Marrakesh last month, one recalls that the designer was an early adopter of the ’60s Youth Quake, noting that because of it, instead of daughters aspiring to dress like their mothers, mothers began wanting to dress like their daughters. Plus ça change …

The fashion industry is often seen as a merry-go-round (no new ideas, just the same things coming back again and yet again); however, with this iteration, the trend has not just social, but political implications.

In a past era, a hoodie was something only athletes wore or was seen only in the gym. With the athleisure trend all the rage for young and old alike, a sweatshirt now lives on the street and has a 24-7 life. It has gained haute fashion status as luxury designer labels like Givenchy tout them while hip-hop artists anoint them über-cool. But depending on your geography and demographic, a hoodie can also have other implications. The black hoodie worn by slain unarmed Florida teen, Trayvon Martin, was one of the reasons along with his race why he was profiled.

But this athleisure trend, kicked off by the sneaker revolution a few years earlier, has been a lifestyle game-changer. Treading new stylish ground, giving older wearers au courant insouciant cool, sneakers are now worn with suits to the office and embellished for black-tie events by women kicking stilettoes to the curb.
This is the most convincing reason why these hot-ticket items should not just be worn at the gym or at home: these pieces are comfortable, a selling feature that’s lost on youth but welcomed with relish by the mature crowd.

But it would appear that millennial dressing is a two-way street. There is an item from the boomer’s closet coveted by the kids.

Footwear News, a trade publication, reported last year that the shoe brand most Googled during back-to-school season – for three years in a row – was none other than Birkenstock.

Here, meet some of the boomer women putting their own unique spin on the millennial style.

Theresa Ioanidis
57, Sales Associate,
119 Corbo

“The great thing about leggings is the ease and how many different things you can wear with it. You can wear it with a big sweater or a T-shirt or a jacket. You can wear it with boots, an oxford or a sneaker.”

Amp up the sophistication level of basics like leggings in a material like leather. Jacket, Céline; T-shirt, Dries Van Noten.; leather leggings, Haider Ackermann; sneakers, Balenciaga; watch, Hermès.

Esa Reia
63, Sales Director,
Reia Studio

“I like the shock value a single item can provide – especially if you take it out of context and do the unexpected. Mixing high and low. Like pairing this wonderfully detailed and intricate jacket – there are 18 seams on each sleeve alone – with jeans.”

Also, dress up jeans with a luxurious touch such as velvet booties. Jacket, the Unttld Spring/Summer 18 collection; tank top, Uniqlo; jeans, Gap 1969; velvet boots by Dries Van Noten, from 119 Corbo.

Roslyn Griffith Hall
56, Stylist and Jewelry Designer

“I never think I got old. I’m still living in the 1980s, baby! That’s when I came to be – being in art school and fashion school. I didn’t have anything so I had to make or create or put together different pieces and that’s become my lifelong style.”

Play Mixmaster with unorthodox pairings, such as track pants with gold boots or a wildly coloured coat. Coat, Dries van Noten; hat, Stetson x Tasya Van Ree; T-shirt, John Varvatos; drop-crotch track pants, Adidas; boots, YSL; Elsa Peretti sterling silver cuff, Tiffany & Co.; earrings, Cheap Monday; all other jewelry from her label, Fitz & Fur.

Susie Sheffman,
58, Creative Director and Fashion Consultant (left)

“I’ve always been more comfortable dressed as a nine-year-old boy than a middle-aged broad! My natural inclination is to be cosy and comfortable. To me, items like a grey hoodie are wardrobe staples. They are quintessential classics – simple timeless designs that you can’t improve upon.”

A collegiate look can be grown up with a menswear-inspired statement coat. Hoodie, Isabel Marant; plaid coat, Miu Miu at Holt Renfrew; reworked Levi’s denim skirt from Preloved; shoes, Tod’s.

Adrienne Shoom
57, Stylist, Creative Director, and Co-founder of clothing label Ware (right)

“I’m always on the search for the quintessential white T-shirt. One that is cotton, crewneck – I’m obsessed with good fit. I often shop in the menswear department especially for French blue or white shirts because I love the fit.”

Layer the modern slip dress with a variety of textures for a weather-friendly take. Slip dress, from her label, Ware; vintage fur jacket; turtleneck, J. Crew; boots, Acne.

A version of this article appeared in the November 2017 issue with the headline, “Millennial Dressing,” p. 67.