1) Can you give us an overview of your background?

I got started writing about menswear in college, purely as a hobby. I realized I liked it way more than writing my thesis, and pivoted from applying to PhD programs in English literature to pitching magazines stories about classic tailoring. After covering a Sotheby's watch auction, I ended up meeting HODINKEE founder Ben Clymer and the rest is history. I joined the company as the first employee in the summer of 2012, and since then have been on a winding journey through the world of watches.

2) What inspired you to get into watches?

I first came to watches as a part of my interest in style and dressing, not from a technical or hobbyist perspective. I was basically just interested in handsome accessories, with no understanding of movements or the craftsmanship that goes into making a watch. After doing some research though, and writing a few stories, I was totally hooked – I'm just a big nerd at the end of the day, and anything that I can go super in-depth on, I can probably get excited about. The same things that drew me to tailoring and hand-made shoes appeal to me about watches.

3) You have recently co-authored an updated version of The Watch: Thoroughly Revised. Have you noticed any changes in watch trends since the original was published?

Oh, for sure! The watch word has changed so much in the short time I've been involved (about seven years now). Collectors are savvier than ever, there's more scholarship, auctions are perpetually heating up, and brands are working to convince consumers that they want something mechanical and luxurious when there are so many other options out there. It's an exciting time to cover the watch industry, for sure.

4) Do you have a favorite feature of the new book?

For me, the best thing about this book is how it can be different things to different people. If you're a collector who wants a reference guide, this can serve that purpose. But, importantly, the historical information in this edition and the updated images provide a great overview for new collectors. When I first got into writing about watches, someone told me to buy "The Watch" as the fastest way to learn and get up to speed – to have the opportunity to work on this updated edition was a real treat.

5) Do you see parallels between the emerging trends in watches and the menswear industry as a whole?

Absolutely. I think people really do want to buy "less and better," to use a somewhat tired cliché. Whether it's investing in a serious watch that you know is going to last decades or splurging for a great overcoat or a particularly nice pair of loafers, I think it's all driven by he desire to have things of high quality that can tell stories. We don't just want to own "stuff" anymore – we want to own stories and ideas.

6) As managing editor of Hodinkee.com, you have a lot of exciting projects going on. What new features or pieces are you excited about?

Haha, hmmm...what am I allowed to tell you about. I think right now our 10th anniversary celebration is one of the coolest things we have on the horizon. In December we'll be hosting a weekend of programming, free and open to the public, all about watch collecting to mark our 10th anniversary. It's our little way of giving something back to the community that has supported us.

7) Do you apply the same philosophy in shopping for watches as you do for tailoring? Do you approach the processes differently? If so, why?

I approach them in pretty similar ways. I want to own just a few things, but things that I really love and use. I got married in a basic navy Ring Jacket suit from The Armoury, and I still wear the hell out of it. This could go for any number of other pieces in my closet or my watch box, but I don't like to have things just sitting there. Whether it's a jacket or a watch, I don't want to have things that I only wear once or twice a year. It just feels wasteful to me.

8) When you travel, what do you pack in your carry on, both watches and clothes, etc?

I've stopped traveling with lots of watches. It's just more to worry about – I usually pick one and just go with it (more often than not it's my vintage Rolex Explorer, which can take me basically anywhere). I dress in pretty neutral colors anyway, but especially when I'm traveling it's all about white shirts, mixing and matching grey and blue jackets and trousers, minimal pairs of shoes, etc. I hate checking bags, so if I can get away with it I try to pack everything in a roll-aboard case. At this point, unless it's the dead of winter, and I need to be in a suit every day, I can basically do 7-10 days without checking a bag.

9) Do you have an item in your closet that you couldn’t live without?

I would say it's that navy suit. I wear the jacket as a blazer all the time, can dress the suit way up or way down, depending on where I'm going, and obviously there are the sentimental aspects of having worn this for my wedding. I hate when people talk about "must-haves" and such – dressing is too individual for that – but if there was something I'd recommend everyone own it would be a solid navy suit. That said, the new taupe covert cloth suit I recently picked up feels like it's going to be a real staple going forward.

10) What's something that people might not know about you?

Haha, oh boy. I've always been really into clothes and style, but it hasn't always been a classic or traditional look. As a teenager I went through a number of phases, including some pretty wild ones – I've owned plaid, Vivienne Westwood–style bondage pants, I had green spiked hair at one point...you get the idea. There are a handful of photos out there if you dig hard enough (these were pre-iPhone days, so photographic evidence isn't as ample as you'd expect), but I have to say I really feel no embarrassment or regret about any of it. At the time, those things allowed me to express myself in the same way my clothes and style choices do today – I was doing the same thing then that I'm doing now, just with a slightly different message.