Following a meandering - though fabulous - career path through events, womenswear and hospitality alongside celebrated American hotel magnate Andre Balazs, a chance meeting in a London club saw Maine-born Ashlyn Chesney appointed as Style Council Director for the luxury online men's destination Mr.Porter, the brother site to Net-a-Porter.com.

As what could literally be defined as the most perfect gig ever, Chesney ricochet's across the world, meeting dapper gentlemen and profiling them on their careers and recommendations on their favourite local haunts.

Where have you just flown in from?
I'm based in London but in the last month I've been in New York, LA, Hong Kong and now Sydney.

Meet the woman behind the world’s most stylish men

Tell us a bit about your career path.
I started in NYC with a boutique company in fashion but doing events, producing fashion shows and photoshoots for womenswear. I then went freelance and worked with Andre Balaz in hospitality.

After travelling for 8 months through Uruguay, Argentina and Paris, I found myself in London to open the Chiltern Firehouse and fell in love with it unexpectedly. It was a hybrid of where I grew up in Maine in the North East of the USA as well as New York.

The Style Council had been with Mr.Porter since it's inception. In 2011 they put together this group of stylish men that provided not only style tips but also for bars, restaurants and hotels. The team had been working on an update but the stars aligned and a after a random meeting in a London club I was brought on to revive it.

How do you find working in a predominantly male world?
I grew up as a tomboy, the little sister in a group full of guy friends. They'd take me under their wing so I feel like I always connected to men a little bit easier anyway. I wasn't the kid who ran around in dresses and thought about my wedding, I was like 'Alright, business; What will my career look like and how do I get on a plane?' and that's what my guy friends were doing. I get the male psyche a little bit more.

Meet the woman behind the world’s most stylish men

Is there a difference with the way men approach shopping?
What we have on Mr. Porter is the Daily and the Journal and men look towards these to educate themselves on whatever they're going to be purchasing. They do more research. So I think an element of that tends to incorporate the female in their life. I don't know a single guy who hasn't taken advice from a female in his life but I think they're less swayed by female opinion than by the research they've done.

What trends should men be aware of at the moment?
We've seen an uprise in streetwear and sportswear as daywear. But I think a well-tailored suit is always a necessity, always a staple. I think the season, the winter, you're seeing a lot more slouchy suits but they still look really well tailored so they're still investment pieces. They're a little bit of a throwback, an updated 80s silhouette, maybe a little early 90s...

And what about that maximalist peacock trend? How could your average lad try that on for size?
I think men tend to play a little bit more with their accessories. So one of the trends we're seeing is maximalist shoes like the Gucci loafers, like the heavy patterns of colour and texture, in a lot of different labels. It's about taking those pieces that are a little less daring - because they can be with the patterns. We just did a capsule collection with Gucci and one of the sneakers is beautifully tailored and has incredible structuring with the Gucci logo print all over it. So they're perfect for a guy who's going to wear straight-laced suits, without a whole lot of pattern. That's that fun element that isn't as much of an investment but allows them to be playful.

You see these suits that Gucci and Prada, these brands are putting out and they're so elaborate - the embellishments, the embroideries and the bright pops of colour and some men are probably a little too afraid to pull it off still. But again this allows them to be playful. And we've seen it with the pocket squares and ties and bags.

Meet the woman behind the world’s most stylish men

What's a label that you're most excited about at the moment?
I'm really excited that we're bringing on Patrick Johnson. So it's an Australian brand and last time I was in Sydney, we went by the studio and they have an incredible space. The tailoring is impeccable. It's beautiful pieces, lightweight linens, easy to travel and pack with.

When I get back I need to go pay them a visit because I would like a little suit by them that I can pack up and throw into my suitcase.

Do you shop on Mr. Porter yourself?
I don't really buy anything unless its on Mr. Porter now. There's so many unisex pieces on Mr. Porter, whether it's accessories or a great cardigan, scarves, t-shirts. They're comfortable. Instead of borrowing your boyfriend or your partners pieces just go buy your own!

Meet the woman behind the world’s most stylish men