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Meet Ashlyn Chesney, The Woman Who Anoints The Most Stylish Gents On The Planet

Ashlyn Chesney and Ali Mustafa

Ashlyn Chesney and Ali Mustafa

Dream jobs are not easy to come by but Ashlyn Chesney’s role as the director of the Style Council at menswear online retailer Mr Porter is a millennial’s definition of an “awesome gig.” Chesney travels the globe to meet possible candidates for the Style Council: dapper, worldly and stylish gents who offer recommendations on the world’s best restaurants, bars and shops. From Dubai-based filmmaker Ali Mustafa to Saudi art collector Abdullah Al-Turki, this good-looking bunch includes creative types, businessmen and tastemakers who know a thing or two about the finer things in life.

We recently caught up with Chesney to find out what it’s like to be surrounded by some of the most accomplished men around on an almost daily basis.  

How do you select the members of the Style Council?

We have a panel of six and we all work together. We meet once a month to go over all of the candidates that have been put forth internally or externally by other members, or by PR firms that have reached out and wanted to submit some of their clients. Some of us internally know people, like friends of friends, so we suggest them, or sometimes somebody will mention someone at a dinner, and we all sit together and select.

What are the main criteria when choosing an ambassador?

I think to be stylish isn’t just how you dress. It’s how you do business, how you approach life. Being stylish is a way of life – it’s not just selecting the right fabrics and the right colors to wear together. It’s a combination of those two things. I’m looking to diversify the group as much as possible, always searching for somebody with a unique background who has decided to go down that unique career path, and to just build upon the group we already have that is also maybe from a different part of the world that we aren’t representing or don’t have as much coverage in at the moment.


Ashlyn Chesney

If you were to choose an icon from the past who epitomizes the quintessential member, who would it be?

Would it be really cheesy if I said James Dean? Or Alexander McQueen? Lee McQueen was probably the number-one reason I got into fashion to begin with. I just found him inspiring and I thought his message was something that was quite unique in the fashion industry. We have Erdem, the womenswear designer, on the council. He’s the only womenswear Style Council member and I think I would extend that to Lee if he were still here because of his mind and the way he travelled, because at the end of the day the Style Council is about travel recommendations, and really experiencing it in a way that most travelers can’t. He would have been perfect.

How do you think men’s approach to fashion differs from women’s?

It depends on the individual. There are different types of female shoppers, but I think if you boil them down, most of them want to look right. Women will listen and follow trends and look for inspiration in ways that I don’t think men necessarily do. Men really go with their gut when it comes to fashion; not that women don’t, but men do it in a way that’s a bit more unique. They are not as easily convinced to try something. Most men I know don’t like to try things immediately. They size it up before they size it on!

What do you like the most about your job?

I think some people don’t understand that it can be a job – that it’s something that actually exists. Sometimes I have to pinch myself as well, because I can’t believe that this has really taken everything I have done and liked in the past [to create this] job. Sometimes it’s a little bit difficult to explain because it is multifaceted, but it’s pretty close to a dream job!


Members of the Mr Porter Style Council

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