"In Medias Res" is a column in which photographer Chris Fenimore links up with some of fashion's most interesting people to see what they're wearing throughout the week.

Where did you grow up? Where do you currently live?

I’m from Minneapolis. That was a good city to grow up in. I lived around the corner from the Walker Art Center, the great modern art museum. I went to concerts at First Avenue, and to a lot of plays. We had a cabin in Wisconsin, about two hours away. That cabin was a big part of my childhood and is still a special place for me. I go there in the summer as often as I can. I’ve lived in New York for 20 years, which is hard to believe. I live in the West Village now, which is a great neighborhood, but I live on probably the least pretty street in that neighborhood.

I think there’s this misconception that the people who work at and use Grailed are only interested in streetwear or dressing in all black. A lot of us come from various menswear backgrounds, and the propensity for dressing well remains, brand names aside. You’ve written extensively about personal style, and I think the main point of your Opinioneer article was missed by some of our audience. Can you give readers some personal style tips?

Ha! Well I enjoyed some of the saltier comments even though they were at my expense. I think people should try to dress like the best version of themselves. That doesn’t mean they have to wear a coat and tie. But I do think making an effort is important. And I think there’s a danger in obsessing over the next thing, because then you are constantly chasing trends; inevitably what you wear will look dated. When you look at a photo of yourself from a few years ago are you embarrassed? Well, what does that tell us? The best dressed men look good ten, twenty, 50 years later. Look at Paul Newman—he wasn’t obsessed with tailoring like Fred Astaire. But he looked great in whatever he wore and still looked terrific in a tuxedo. I think that clothes should serve you and your personality. That’s what the history of tailoring is—that a suit of clothes made sense for your figure, your face, your coloring, your position in life. You don’t have to go to a tailor to follow those principles. But I do think it’s worth asking if something makes sense for who you are and present you in the best light.

I have a feeling tailoring, or the very least, dressing more sharply, is on its way back. What I mean is, we’ll see more of it on the runway, and more of it on social media. Do you pay any attention to high-fashion, or runway shows? Do you have any favorite brands from that realm? If not, what are some of your favorite brands?

People regularly talk about the return of tailoring. I think it will never go away for many people. For others, it will appeal to them because there’s always a reason to wear a coat and even a tie. It’s about finding the way that makes sense for you. It doesn’t have to be remarkable Italian tailoring—look at Jarvis Cocker. He looks completely like himself, he usually wears a coat and a patterned shirt. It’s not clear where he got them, they could easily be second-hand. He makes everything his own. That’s what appeals to me. You are more important than a brand. The clothes should reflect you. I like Massimo Alba for that reason. His wonderful Italian clothes are thoughtfully designed and very well made. But once you have them they feel like they really belong on you.

Do you have a favorite store in New York City? How about in the world?

I love the Drake’s store. The clothes are very smart and the accessories are terrific. Massimo Alba in Milan is fantastic. Beams+ and Beams F in Tokyo are my favorites. There are so many great stores in Tokyo it’s comical. They really have it figured out.

I know you have a book coming out shortly, and you’ve already written a New York Times Bestseller. What is the subject of your new one, and do you have any specific process for writing a book?

My new book is called Men and Manners and it makes the case for men behaving better. It feels like there’s a lack of civility in public life, I think a lot of people sense that. I write about taking time to try to do the right thing, we usually know what it is, but it’s just a matter of trying to do it. Hopefully the book speaks to that and manages to have a light touch. I hope people respond to it. There are wonderful drawings from a great graphic artist Christopher DeLorenzo. They really set the tone for the book. And I talked to a lot of men about what they thought about manners today—questions, things that bothered them, things they aspired to. But I’m sorry for some of your readers I am still against sweatpants!

You asked about writing a book. It’s really rewarding and occasionally very aggravating. Sometimes I feel motivated and productive and write quickly. Sometimes I don’t feel any of those things and I pace back and forth a lot. I really enjoy the process of making a book, working with John Gall, the amazing creative director at Abrams, my publisher. He comes up with ideas for how things will look and feel. That's exciting, because it’s a real collaboration in the best sense. People coming together to make something better than they would do on their own. And both books are much more interesting because of what he brought to them.

How would you describe your own style? Who and what influences you?

I think I dress sort of like an Italian uncle. I love Italian tailoring and the daring way men there dress. But I also love the more sober English sensibility. I think a combination of those things takes you to a pretty interesting place.

What qualities are you most attracted to in a person? What does it take to grab your attention?

I like people who have a strong sense of who they are. That’s a combination of confidence and humor, but also a certain self-effacing quality. You don’t want to take yourself too seriously. I still laugh about one of your commenters who said it looked like I had sex in dress socks. That’s just a great line.

If I want to buy a suit, and some wardrobe essentials around that suit for looking presentable at work and during the week, what would be your advice?

I think you want to buy the best blue or grey suit that you feel comfortable in and that you can afford. That can be at J. Crew or Ralph Lauren or right on up to a tailor. Don’t be intimidated in these places. Find somebody in the store who appeals to you and ask them for help. If a jacket doesn’t feel right through the arms then say that. Of course it’s hard to speak freely, but don’t leave with something you aren’t excited to wear. I also think the blue blazer is amazingly versatile. If you wear one with grey trousers that does everything a suit does and you can also wear it with jeans or whatever else you want. An unstructured blue blazer is probably the most useful thing you can start with.

What does a typical weekend look like for David Coggins?

An ideal weekend is going fly fishing in the Catskills. But I can’t do that as often as I like. When I’m in the city I try to go to the greenmarket on Saturday morning. Sometimes I cook. I usually do a lot of reading and writing on the weekends. It’s easier for me to work then for some reason. I drink a fair amount of wine. Sometimes I’ll meet friends—I love small bars, like the new Banzarbar. I also love Cafe Altro Paradiso. A great restaurant with a great bar. The bar at Via Carota in the afternoon, before it gets busy, is great.

What’s your ultimate grail?

I often think about bench-made English shoes. The pair you get and then you don’t need any more. They cost a fortune. But for something that special I don’t know if it’s better to have it or better to continue to want it. Because once you have it then that’s it. There’s nowhere else for you to go. Sometimes wanting a thing is actually better than having it. In fact it almost always is.

Tags: tailoring, sartorial, street-style, photography, david-coggins, in-medias-res