I’ll be answering questions periodically, so feel free to ask about travel, style, fishing and other urgent topics of the day.

Cheever or Updike? -Stephan

Cheever. He’s one of my favorite writers in any era. The short stories are of course great. I have slowly been working my way through the journals, which is some of my favorite writing. Wonderful descriptions of New England seasons, loving portrayals of his family. And it’s marked through with sadness from his alcoholism and the fraying relationship with his wife and the reluctance to acknowledge his own nature.

I really enjoyed A Room with a View. Thanks for the film article! Got any book recommendations? Would love to read more ‘favorites’ articles. -Howard

Thanks Howard. I’ll make a book list, that’s a great idea. To start with I love “Between Meals”, by A.J. Liebling. It’s about his time in Paris as a student—actually he stopped attending classes at the Sorbonne after the first week. Then he dedicated his time walking around the city and eating. It’s a wonderful education—he was the New Yorker correspondent in Paris during WWII. In many ways, he led a sad life. This was his masterwork. I would also look up Peter Fleming, Ian’s brother, who was, in fact, a much better rival. He traveled widely. “One’s Company” or “Brazilian Adventure” should get you in the mood.

If you could only buy one pair of shoes, which would it be, and why? -Jason Crouching

Alright Jason. That’s a big and difficult question. My finalists would be the Gardner boot from R.M. Williams, any of the beautiful suede shoes from Crockett & Jones, the amazing new brown desert boots from Drake’s and a Baudoin & Lange Sagan loafer. But I’ll say the suede Alden Chukka boot. It’s versatile and classical and can be worn year round in any city in the world.

I couldn't wait for your reply/post on the best ways to get started with fly fishing so I went and ahead bought a waxed canvas 4 piece rod case with the hopes of filling it over the next few weeks as funds permit. Now friends tell me I should have opted for a simple PVC pipe. Did I start on the wrong foot? -Dave

So glad you started fishing! You did nothing wrong getting a great case. You will find what makes sense for you. I have an old canvas Filson case that I love and use most of the time (they reintroduced it a few years ago). Sometimes I just put the rod tubes directly in a big duffel bag for long trips or in the back of my car. But that doesn't stop me from looking for old Orvis rod cases on eBay!

What are your 101 tips for a timeless style? In this era of fast trends, it is easy to get lost. -Louis-Philippe

How long do you have, Louis-Philippe? This is the big question that underlies everything we wear and how we wear it. I like to keep things simple and on the traditional side. So I gravitate to places that have the same approach—Drake’s, Massimo Alba, Ralph Lauren. I think color and texture are your allies. I like oxford shirts and knit ties. A good, unstructured sport coat is the most useful thing you can own. And then you can experiment once you feel like you’re on stable sartorial ground. I generally think it’s a good thing if you’re more interesting than what you wear, you don’t want to disappoint people when you open your mouth. Good luck!

In today’s day and age, is the hand-written letter antiquated? -NWI

Absolutely not! I think everybody responds to the personal nature of a hand-written note. It takes time and is thoughtful and if anything it stands out more now than it ever has before. Get some engraved stationery from Terrapin and you’re in business.

I have a wedding in September at a coastal New England country club. The dress code is black tie optional. Can I wear my favorite navy suit? Do I actually need to wear a black tie?

Black tie optional is a tough formulation. They should make it clear. But optional is no option at all. You could get away with a devastating navy suit, but why not set the standard and wear a tuxedo?

Thoughts on beard grooming/style such as length, clean neck with defined line vs a faded softer look, etc?Additionally, favorite post-flats libation and where to enjoy it on Long Island? -CMK

These are very important questions! I don’t like sharp edges to beards. Remember: there are no straight lines in nature! The fade is the key, go to a professional. I go to Mark Miguez at Matter of Instinct on Orchard Street, he’s a true expert. Then I have lunch afterward at Russ & Daughters Cafe across the street. As for Long Island, I love the Dock in Montauk. Still the best.

What cigars do you enjoy smoking? What are your go to’s -DCE.

I like the classics, or what I consider to be the classics. Hoyo de Monterrey, Epicure No. 2. Partagás, Serie D No. 4. More and more I enjoy any Trinidad. I also smoke those Tuscan cigars that are really quite brutal. My cigar rule is only smoke outside when you’re not near people. It’s quite an imposition. And too many men smoking cigars in one place is usually a bad sign.