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Interview with Dan Flores


September 19, 2013 by Ville Raivio

‘I am 37 years old and was born and raised in East Harlem at the northern end of Manhattan. Although I purchased a home in Maplewood, New Jersey, a few years ago, I still commute to the city everyday and consider myself a life-long New Yorker. I’m an attorney. I graduated from Cornell University in Ithaca, New York with a BA in History and Political Science. I also have a JD from Fordham University’s School of Law. I am married with three children – all under the age of three! My wife has always been willing to let me indulge my sartorial interests. During law school, she actually worked in the legal department at Chanel, which got us into a few amazing employee sales at Holland&Holland.


At the time, the company had a brick and mortar shop on 57th Street. So you could say that she has actively encouraged my interest at times! My children, on the other hand, might be the only kids learning their numbers by counting shoes on the shelves in my closet :-) Well, toddlers tend to take up a lot of one’s time! So between work and being at home with the family, for the last few years the rest of my free time has been split between the writing that I do for An Uptown Dandy, and the research and writing that I’ve been doing on The Best Dressed Man In The Room.

I would say that I’ve always had an interest in clothing on some level. It probably started as more of an interest in what was fashionable at a particular point in time which gradually gave way into what I would describe as a more internalized sense of style. So although there was a period where I was in the street wearing Larry Bird jerseys and had a closet full of Timberland field boots (and still do), at the same time I was putting on formal wear at 13 or 14 years old for an evening at the Waldorf or the Plaza (for a Boys’ Club of NY dinner or a friend’s bar mitzvah). And I enjoyed those experiences, so there was always an appreciation for both current fashion and timeless style. At the end of the day, a 19-year-old with 10 pairs of barely worn Timberland field boots in different colors sitting in his closet has the same DNA as a 35-year-old with a closet full of men’s shoes made in Northampton by Edward Green, John Lobb, Gaziano&Girling, etc.

Interview_with_Dan_Flores_at_Keikari_dot_com2The Best Dressed Man in the Room: release date September 24th

That appreciation had a lot to do with my parents, actually. They certainly could care less for the jerseys and boots, but they both had an appreciation for classic men’s style and quality tailoring. My mother was a seamstress for many years, at one time working and touring with the Joffrey Ballet (my mother is approaching 70 and friends and relatives still ask her if she would be willing to make a wedding gown from scratch(!). So she knows what good handwork looks like in a suit and has an eye for the drape and fit of men’s clothing. I think an interest for clothing runs in her family, as her father was considered something of a dandy.

My father was also very much interested in men’s clothing at an early age. He went to high school at Central Commercial on 42nd street in Manhattan, across from the old Automat, and he worked at Paul Stuart on 45th Street after school, in the men’s shirts department. I remember we went in together one day and he mentioned that he used to work there in the late 1950s or early 1960s. I don’t know if they didn’t believe him, but they brought out another gentleman who apparently was the company’s longest-tenured employee. He proceeded to ask all kinds of questions about my father’s time there: which department he worked in, who was in charge there, where the department was located in the store. And my father remembered everything! And he did that on several occasions in other men’s clothing stores as well. This was, after all, a man who claimed with great pride that one of his most prized memories was helping the owner of Mr. Grey’s Ltd. wait on the Duke of Windsor one afternoon.

Interview_with_Dan_Flores_at_Keikari_dot_com3The inspiring grandfather, Eusebio Delerme

So it was really my father who taught me the basics about men’s clothing — how your shirt cuff should sit under the suit jacket, how the pants should break, things like that. Of course, I think you would have to say he was a dandy – he preferred to wear suede Bally loafers and his idea of casual wear was a deep burgundy guayabera shirt over an odd pair of trousers. So it was certainly a unique situation to have two parents that could comment on the fit of a garment, as well as on the quality of the construction of that garment. It definitely gave me a better sense of what to be on the lookout for.

I generally wear a suit or an odd jacket and trousers for work — I hesitate to say that you can normally find me in business casual attire, because that means so many things to so many people. But if I’m not wearing a suit, then I have on a sports jacket or blazer with wool slacks or khakis. The phrase “no brown in town” does not apply to me. I generally wear brown shoes 6 days a week — on Sundays I wear my Rod Lavers. I think that I am down to two pairs of black shoes now — a pair of black semi-brogue cap toe Grenson Masterpieces for Paul Stuart’s Stuart’s Choice line. The other pair doesn’t get much wear — vintage Johnston & Murphy Handmade 100s; black wingtips with a spade sole and that original box with the draw strings and the red velvet lining — a testament to a time when American shoe makers could hold their own against anyone else in the world.

I don’t really favor one particular style or cut over another. I definitely wear more single-breasted jackets than double-breasted, but I like them both. I suppose I have a preference for trousers with a flat front. I enjoy the English cut as well as the Italian — the two navy blazers getting the most wear in my rotation at the moment are a 3-button Borrelli and a 1-button from Huntsman. I know that some people will say, “Well, they’re both navy blazers, aren’t they?” That is true, but they are just so different!

Interview_with_Dan_Flores_at_Keikari_dot_com4Tools of the blogging trade

For suits, I would probably have to say that Ralph Lauren’s Purple Label is my favorite. I love the aesthetic, and the ready-to-wear model in size 42R fits me pretty well (in my opinion). My favorite suit is a 3-piece, 2-button single-breasted with double-vents and peaked lapels. I call it my “George Raft” suit. G. Bruce Boyer once asked me if it was bespoke, so I like to think that means that it’s a decent fit. My current sports jacket favorite is a dark brown 3-button from Drake’s of London. It’s a cashmere and silk blend that is just very soft to the touch — an Italian cut with a really soft shoulder. It goes great with their Fair Isle cashmere sweater vests.

As I mentioned, my earliest exposure was through my parents, and from there I began to learn more about men’s clothing from various internet fora and like-minded individuals there with the same passion and interest in men’s clothing. From there, I began to meet some of the artisans behind some of the shoes and clothing — it has been a pleasure to meet the people behind the things that I enjoy to wear, whether its shoes or ties or whatever the case may be. People like Chay Cooper at Wildsmith or Gianni Cerutti at Passaggio Cravatte are professionals who have a vast knowledge in their respective fields. But, at the end of the day, they’re also people with a deep passion for their craft and professions, so it is very easy to communicate with people who share the same interests.

Interview_with_Dan_Flores_at_Keikari_dot_com5Gangster Giuseppe Doto in a 1937 police mugshot

That underlying passion was also behind my work on The Best Dressed Man In The Room. My father used to tell these great stories about the larger-than-life racketeers of his father’s era. He heard some of those stories from his father probably, and perhaps read about others, and others were just these neighborhood stories that the old-timers used to tell. My father, of course, would always add these sartorial flourishes to the stories, being sure to point out things like whether someone was known for wearing the ubiquitous pearl-grey fedora associated with the gangsters of that period.

What made these stories even more amazing was that they all happened in our neighborhood. Vincent “Mad Dog” Coll gunned down a sidewalk full of kids right up the street from our apartment building. Dutch Schultz got into a shoot-out with New York City detectives right on Fifth Avenue, just up from the entrance that I used to take to get to my little league games in Central Park. My grandmother lived right up the street from Venezia, an old Italian restaurant on 118th street where Jewish gangsters like Jacob “Gurrah” Shapiro and Louis “Lepke” Buchalter would meet with their Italian counterparts from the Little Italy section of East Harlem, around Pleasant Avenue.

I originally described An Uptown Dandy as “the nocturnal ramblings of a sartorial bon vivant.” The “bon vivant” part notwithstanding, that is exactly what it was. I literally enjoyed rambling on about certain subjects and I felt like I was boring people to death (like my family and friends, who had heard all of these things a million times before), so I thought a blog would be a good way to connect with people that also like to talk about Edward Green shoes, trips to Saratoga Racetrack, and the golden age of men’s style and the New York City sample sale. Eventually, I was able to interact with people with similar interests in many different ways, like contributing to publications like The Rake, or other blogs like A Suitable Wardrobe, or interviewing people like Hilary Freeman of Edward Green, or Chay Cooper of Wildsmith, or Gianni Cerutti of Passaggio Cravatte. The heightened level of interaction with people whose work I admire and enjoy is definitely the most rewarding aspect of the blog.


I like to keep things at least tangentially related to men’s clothing and style in general at An Uptown Dandy. But sometimes I go a bit off topic, but that is one of the great things about having your own blog. Whereas An Uptown Dandy focuses on a variety of topics relating to men’s style, The Best Dressed Man In The Room explores the forgotten style icons of the Roaring Twenties and Depression-era Thirties — the vicious but often colorful criminals that filled the tabloids with tales of their legal misdeeds and sartorial adventures. There was a reason Hollywood employed young stars in the early 1930s like Gary Cooper and Clark Gable to play anti-hero racketeers on screen — the public had already shown itself to be fascinated by the real-life characters upon which those pre-code films were based.

In addition to the essays that I contributed to the book — essentially profiles on a few of the more sartorially inclined characters from that era — The Best Dressed Man In The Room is a collection of images taken from private collectors, photograph collections and newspaper archives. The aim is to show, with the use of forgotten and, in some cases, quite rare images, that some of that era’s more infamous underworld characters were very interested in making a sartorial statement in line with what we would today consider to be classic men’s style. If anything, the term “gangster” style, then, is something of a misnomer. These men were just stylish — period.

A friend of mine actually told me about Styleforum way back in the days of the Benny’s of Atlanta fire sales on discounted Grenson Masterpieces. I believe they were stamped for Paul Stuart, and they were reduced to $150 from something like $500 or $600 at the time. So it was a great source for getting information on good deals like that. Then I stuck around as PhiloVance to “listen” in on conversations about brands and craftsmen that I was unfamiliar with. Of course, as I became more knowledgeable, the subjects became less interesting and more repetitive. Which I suppose is the nature of the various internet fora, to some extent. New people with a thirst for knowledge come along, and other people move on.

Interview_with_Dan_Flores_at_Keikari_dot_com7Vintage Edward Green collection

[My tips:] Don’t slavishly adhere to someone else’s notions of what constitutes style. Part of the fun of the journey in developing your own unique sense of style is trying out different cuts, colors, fabrics, textures, and patterns. The fun is in the experimentation. The worst case scenario when you try something is that you might not like how it looks on you. So take it off and try something else on. Be yourself and follow your own journey.’

The Best Dressed Man In The Room: A Photographic History of the Sartorially Inclined Goniffs, Gamblers, and Gangsters of the Inter-War Years, 1920-1945 is available in eBook format for iBooks at, Hardcover in charcoal grey linen with dustjacket, and Deluxe Edition with wrap-around image cover and premium lustre hard paper stock.

Photos: © Dan Flores


  1. Walter Matera says:

    As an aspiring blogger from the sporting/country gentleman point of view, I am inspired by your passion and devotion. I have become a regular reader of you site and look forward to getting the book when it hits the market.

    To dressing well!


  2. RJ says:

    Great interview and insights.

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"If John Bull turns around to look at you, you are not well dressed; but either too stiff, too tight, or too fashionable".
~ Beau Brummell