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Nickelson Wooster could easily be described as a misplaced millennial.

The tattooed menswear tastemaker may have been born in 1960, but his view of topics such as career paths, style conformity and social media easily mirrors those held by Generation Y.

a certain way, I have been the unlikely beneficiary of appearing today how a lot of kids are appearing meaning these social media influencers, Wooster says. the difference is, I twice their age and with a lot of experience under my belt.

Perhaps that why Wooster (who goes by Nick) boasts a following of more than 600,000 on Instagram and is a fixture in street style coverage from fashion weeks around the world.

But it not just his edgy chic appearance and online presence that endears him to a younger set (although it certainly helps). It also his career trajectory. To say his fashion work experience has been varied if a tad volatile would be an understatement.

nature of employment is changing and I think kids are going to have a career much more like mine than people my age have, which is to say they have probably worked at one place for their entire career or two places for their entire career, Wooster explains. always say, I have been fired from more jobs than most people would ever have had in their entire career.

Wooster lengthy success in the industry is not an accident, though. Not even close. His nearly 30 year career in the fashion industry flitting between several high profile positions including as a buyer at first Barneys New York; men fashion director at Neiman Marcus; the director of retail merchandising at Calvin Klein and design director at Polo Ralph Lauren have all been calculated jumps.

So, what drove him to make the leap professionally so many times?

me, it pure ADD. I have just been interested in a lot of different things, he explains. I was also ambitious. I wanted to try different things. Wooster leapfrogging hasn always been viewed as a bonus. In fact, as one might expect, it was often a point of concern for prospective employers.

“It wasinteresting because Karen Katz, when I mether at Neiman Marcus, was very critical of my jumping around a lot. And headhunters have also said the same thing,” he says. “And I would say, ‘OK, if that’s the filter by which you’re looking at success, is longevity, which is absolutely a metric. But I don’t know that it’s necessarily the right one.

Wooster’s latest project is designerof a capsule collection for the Italian fashion houseLardini, which is what brought the fashion insider to Vancouver’s Holt Renfrew on Oct. 7 to showcase select pieces from the launch.

A model wears a jacket from the Wooster + Lardini collection. A selection of the release is available at Holt Renfrew in Vancouver.

The release includes coats, cardigans and drop crotch trousers, each piece with a little something different and unique about it just like the man who created them.

I tried to do with the clothes that have my name on them, is every item is a little different take on something that out there, he explains of the designs. the most part, I would expect or assume that no one is going to wear head to toe me because I don believe that head to toe anything is very interesting.

men don do that. That like a costume. Wooster hopes the collection offers customers classic pieces with a twist such as patchwork shirts and a blazer with dot details and a few comfort pushing pieces as well.

tried to develop pieces that, each standing on their own, would be a variation on something familiar so it could be imagined that if you wear this it could fit into your wardrobe, he says. drop crotch pants, I get that not for everyone. It not easy. But, as we were putting the collection together we said, OK, the world has lots of normal pants so what something a little bit different? who is Wooster target customer?

really believe there are three guys that shop in better stores, Wooster explains. is a guy who is style aware but fashion averse, so someone who is interested in looking good but the minute you give him a look that is identifiable, he not interested; the second guy is absolutely a fashion victim, somebody who loves labels, loves fashion and wants to tell the world I know what I doing; and the third guy is super classic and would only wear Brioni. is confident there are enough pieces within his Wooster + Lardini collection to appeal to those first two types of shoppers.

with a small collection like this, I recognize that we can serve everyone, but hopefully enough fashion interested shoppers would be able to find something, he says.

Chatting with Wooster gives one the impression it a good time to be a man interested in what he wears, as he animatedly discusses the ways in which men style barriers and stereotypes have loosened. Basically, it no longer considered less masculine if a guy wants to think about what he wearing.

divide, 25 years ago when I started, it was exactly this: gay and straight. Gay guys would wear designer clothes and be, let say, peacocks, and straight guys would never want to do that, he says. always say that MTV cribs is what brought straight men into the fashion world. Once they sort of saw sports guys and music guys had like a billion sneakers, they realized, you mean I can have more than one? says it wasn until the early aughts (or 2000s, for those not in the know) that men expanded their footwear thinking to go beyond a black shoe, a brown shoe and a pair of sneakers.

they saw a closet full of white sneakers they realized oh, shit! he says. think, for most men, because barriers have come down, there are so many more options.

Wooster says, in addition to a push from pop culture, social media platforms such as Instagram are prompting men yes, even manly men to get excited about clothes.

is no right and wrong. And I think, for the first time, all channels are open, he says. if you do want to wear a skirt or a dress, even a blouse or carry a handbag, you can. pointed to blogger Bryan Yambao, who is arguably considered one of the first breakthrough online style influencers, as an example of this fluidity and freedom.

clearly a guy, he not trying to be anything other than that, but he totally wears women clothes and carries a bag, he says. think that an amazing place because, 25 years ago, that wouldn have worked well for that person. They would have been very marginalized. And I think now, he sitting in the front row of all the shows and doing really interesting things. And I love him for that. the freedom of men fashion has left some men feeling alienated, Wooster says.

think that on the flip side of that, it has left men who don prioritize clothes, more at a loss than ever about what to wear, he says. dress codes changed and the suit went away, it fcked guys more than anything. ease of the menswear of a suit and tie allowed those who couldn care less about clothes (the third type of male shopper, if you keeping track) to still look stylish. In place of suiting, several professionals such as the late Steve Jobs and Facebook founder Mark Zuckerberg adopt a version of their own in order to take the guesswork out of dressing.
polo gear a great time to be a guy