My Entry into Fine Menswear

Inspired by:

Early life, Education, Sports, MadMen, McQueen, Cities, Business and Love.

I’ve been wanting to write about this for a while. My recent flurry of commentary and various illustrations across different mediums, exposing my love for menswear, and the reasons behind it. It’s a nuanced word. Menswear. Although it does mean a piece of clothing that a man can wear, the word has a higher-order meaning among those who live, breathe and sleep it every moment. This community is an incredible ecosystem of human beings. Regardless of zip code or body structure, there are a good many gentlemen that view menswear as an extension of luxury and genuinely love it as I do. I am no longer alone.

Now, having written my first book, focusing on fashion and the ancillary impact of software, called ‘Ripple: Craftsmanship worthy of the Abstract”, I find myself needing to preface how I got to the point where I am wrapped up in this universe of podcasts led by men with English accents and thoroughly well-spoken English. A universe where I’m either reading a book on menswear and fashion, listening to a podcast or glossing over the catalogues of the companies mentioned in the aforementioned podcast.

Many of the folks that chat or blog about menswear, especially fine menswear, are located in New York and London. It is really where my perceived nucleus of this all is. I will compare New York, London and the other key cities in other articles (Milan, Paris, Naples), but here I want to talk about how I ended up in a position where I lovingly attempt to discern, wear and explore the world of menswear, luxury and the finer things life.

The question for me and for those of you out there who have stories that may resonate: How did a kid, who was born in Massachusetts to immigrant parents, then majored in Computer Science with a minor in Journalism, play collegiate hockey, joined a fraternity, worked primarily in software, startups and audio production & recording end up completely immersed in fashion, fine menswear and luxury?

For background, I currently am the founder and CEO at Blackbird, a company that connects creative professionals with new and fresh opportunity, and am working on a stealth software project dubbed ‘Ripple’. This project, (wait for it…) is software tailor-made, handcrafted for the world of fashion and apparel. Perhaps destiny does play itself out and my two favourite worlds can collide. I will keep you closely updated.

Back to my love for menswear. The title hints to it, but let’s start at the beginning.

I was a kid in Massachusetts, living in a predominantly Irish-Anglo neighbourhood, where I literally went to school at a Catholic church. I had to wear a proper uniform, similar to a little kid’s version of a suit. New England definitely has its own style, and as the eldest of two brothers, I remember this very fondly, although I would not let it manifest until much later in life.

Blazers, peacoats, scarves, earmuffs, mittens in the winter in addition to the “I’ve got a boat docked at Martha’s Vineyard” look in the summer. Beautifully brought to life by Vineyard Vines by the way. A company I chronicle in my book. They don’t use real models. Only real people who happen to be wearing their clothes. Imagine the CAC! (Cost per Customer)

There was no denying that New England had a unique style. Dominated by what is often referred to as the ‘Ivy’ style, made popular by JFK, Harvard, MIT, and the academic and business elite, who would often wear their heritage family or fraternity crest as a pin on their jacket or stitched onto their tie. A blend between Irish woollens, Anglo-Saxon structure, and American Ivy league evolution.

I was about 12–13 years old when my dad figured he could continue his business on the sunny west coast, where there was a budding tech scene, in which both of my parents were apart of. Both with their own style. My dad was the entrepreneur, going on to start a public company that exists to this day called BoardwalkTech, which has the best data absorption cell database in the world. (This will become important later). My mom was the executioner. She didn’t value time ‘wasted’ sitting around, brainstorming over a beer and goofing around. Frankly, initially, that is what a lot of entrepreneurialism is. Sometimes you’ve got to open the bottle and let the ideas flow. But she was a bottom liner and better yet, she knows how to code, rapidly learn new digital frameworks and she wanted to and continues to apply these skills and get paid. And so she does, currently working for Slalom. Their careers and their love for their work shaped the way I learned at home. In addition to school, I also had to do deal with my tutor, aka my mother.

I bring this up because the way you are brought up shapes parts of how you are today. That being said, I suppose it’s important to note that my parents didn’t care about fashion. It was viewed as a general opulence. There wasn’t hatred or disdain. It just wasn’t discussed or emphasized like say my piano lessons. The folks had their ensembles for dinner parties, for which they didn’t really care for, but other than that, they were rather apathetic to the notion. Treating dressing up as a chore, as opposed to an art. To me, I rather enjoyed dressing up in my uniform for schools. I oddly enjoyed watching my dad iron clothes. I loved the smell of starch and the aftershave he would use after shaving.

As a kid, I was an athlete and a relatively good kid in school who enjoyed the company of many friends at any free moment I had. I was definitely a Dennis the menace on the other hand. Running off whenever I could on my bike. Getting into trouble. Nothing malicious, but that bouncing the basketball till the wee hours and setting off fireworks when it wasn’t 4th of July. We played baseball and broke windows. The hockey team that most of my buddies joined kept us in line for the winter but apart from that, it was relative mayhem. In New England, this meant about 1 to 2 seasons of the year. Weather often rained on the party.

There was, in New England, and especially Boston and it’s suburbs a sort of implied emphasis on your prowess both in athletics and in academics at what I felt was an early age. This is in stark comparison to where I would move.

When I moved to California, I had these new friends. Kids who didn’t know how to tie a tie and some of those friends still don’t. They didn’t play baseball. They didn’t know how to ice skate. The public school we went to made it so no one knew or cared what each other was studying. They wore whatever they wanted. I ended up hanging out with the ‘skate crew’. An outspoken and naturally rebellious bunch, as “no skateboarding” signs were scattered everywhere in suburban California. We were the group of kids whose parents were at work long enough for us to hang out and impress the girls by hurting ourselves on a ply of wood. There was still a ‘code’. If you were a skater kid, you dressed like a skater kid, with your own style stitched in. This meant Nike SB shoes, Santa Cruz shirts, Levi’s denim pants. The counter culture was immediately evident. “I don’t want to play for the MAN” — a friend remarked as we melted a candle onto some concrete, making the concrete slicker so that the skateboard would slide better when you hopped on it.

There was another influence at the time of adolescence; that was music. From Sublime, Grateful Dead, Led Zeppelin, 2pac, Blink 182, etc. The list was nearly endless. The style of these bands would weave its way into what we considered to be cool. And in reflection, it’s interesting that at such a young age, having something unique to yourself was something that was held up high in the virtue department. You did not wear or buy clothing, shoes or sunglasses that someone already owned. ESPECIALLY in the same color. You’d likely be kicked out of the clique. So the only true uniform in this ‘world’ was the uniform I had for the school baseball team.

There was another uniform though. Something I had brought with me from Boston. Hockey.

I was 12 during the trans coastal move and I was cognitive enough to remember and miss Massachusetts. Playing hockey was something I always loved and it became a subconscious tie and expression to my roots back east. The love stemmed from a combination of the love of the ice-cold breeze hitting my face at high speeds, the skill, the physicality, and the girls, especially in New England. You have to your wits about you no doubt. Most of all, it gets the adrenaline pumping. To myself and my family's surprise, the Jr. Sharks, were nearly as competitive as my teams back in Burlington, MA. They were a product of the professional San Jose Sharks NHL team, created in an effort to foster the growth of the sport by strengthening the channel of talent for the future.

I still play hockey to this day and played for BC (bringing me back to the east coast as a late teen) and later San Jose State, where I would graduate in Computer Science and Journalism. I’m shooting from memory, but I believe it was the coach of my triple-A 18 under team (an elite travel team for 17 and 18-year-olds), who made me buy my first suit since my days in Boston. We were traveling as a team to cities on airplanes. Our uniform off the ice was the suit and variations thereof.

Our coach was old fashioned. Literally, his go-to choice of a cocktail was the old-fashioned with bourbon. He was from Wisconsin, was an ex-Vietnam war veteran and an ex-Boston PD detective.

He wanted you to suit up properly. You could mix and match. It didn’t have to be the matching two or three-piece suit. It just had to work. There were a couple of constants. A sport coat, trousers that fit the outfit, a tie, and a tie clip. There was one more. I love this one because I now have all these cool, rare cuff links. If you were going to wear a collared shirt and tie, you had to wear a french cuffed collared shirt and cuff links.

He gave you freedom, but it had to be well done. If something was off, he had our captain come over and correct it. If you made the same mistake twice, he’d send you home or rip your airplane ticket in your face and your parents. He sent a kid home from Logan Airport because the kid's tie was too short. And although I feel bad, the tie was tied way too short. Clown short. It took me a while before I could really dot the I’s and cross the T’s. It would get better with time and it ultimately taught me how to dress like a gentleman and for the occasion. For example, there was the sport coat done right for the airplane, but a suit and tie before the hockey game, especially if it was a big opponent or a big game. Then there was what you wore to dinner. And if you did it right, our coach might let you have a beer at the restaurant.

Subconsciously, he was showing us that there was a secret club that you entered if you dressed well. Later in life, people would call you sir. They would buy you a drink and give you business cards. More doors seem to open when you are dressed well, but more importantly, dressed in way that makes you feel empowered with genuine thought behind the blazer, trousers and the outfit in general.

My first suit was bagging, and not ‘suited’ to last. Still, I felt cool wearing it. I felt like one of the heroes in the movies my dad would watch. This would turn into a love affair that I tucked away until my early 20’s. In order of importance, my dad had me watch the Great Escape, The Thomas Crown Affair, and Love with a Proper Stranger. I remember him remarking how Steve McQueen walked like he had not but a weight on his shoulders.

From then on I was hooked. Not from a fashion standpoint, as I had little to no money, but I wanted a motorbike. I wanted to impress the ladies like McQueen. I wanted to walk like Steve McQueen.

It wasn’t just McQueen movies. He showed me Bridge over River Quai, Agony and Ecstacy, Patton, Lawrence of Arabia and so many more. I read a lot too. For Christmas, my dad would buy me books. That was it. Take it or leave it. So I took them and I would read them. From Animal Farm to the Grapes of Wrath. It armed me with an understanding of the world, that I felt was different from other kids. Not that I felt that I was better, but when many subjects would be casually glossed over, I saw a deeper backstory.

Of course, in this abridged version of the story, my mom storms in to remind me that I need to submit my 15 college applications. I don’t know why there were 15 because there was a general consensus between my friends and me that we were going to UCSB, Chico or ASU. Easily the top 3 party schools in the nation, or the world.

I took the lessons in dressing properly with me to college. But initially, at the University of Santa Barbara, with the beach, I found myself wearing less clothing. A majority of the time going shirtless. This lack of structure messed with some screws and my grades plummeted. I picked up a bad boy attitude and got a couple of tattoos. Something that was always inside of me, but manifested itself during these early college years.

Upon hearing about my grades, my mom was furious and literally “shipped me off to Boston”, where she said I would play hockey for Boston College. I responded by doubting the fact that I would even make the team, let alone be allowed to transfer. She didn’t care if I made the team as long as I played the sport. “Ask them to join the practice team” she implored, having been an alum of the school herself, I’m guessing she pulled some strings because I actually made it. With school, hockey, partying and hardly any money, my thoughts about widening my wardrobe had taken a backseat. But I did still pick things up along the way, quietly discerning how the collegiate ecosystem dressed for various occasions. I joined a fraternity, Delta Upsilon, which really emphasized dressing up and being a gentleman. A notion that is thrown out the door when the weekend arrived, but none the less, it was a pillar of the multinational organization.

After two years at BC, I got an email from the head coach of San Jose State hockey. A growing and increasingly competitive team, led by coach Phil Hazelwood. The very same coach I had when I was on the 18 under team. The very same coach who emphasized being proper.

He generally viewed the world as being disorderly, compared to the golden age in which he grew up. When flying in an airplane was a dignified affair. Where one didn’t just climb out of bed and walk on with their sweatpants. He would blame our generation for allowing this to happen, which he explained had resulted in a less than stellar airplane service, compared to how it once was.

I was back in California again, and I realized that although I was born in Massachusetts, I had lost my accent and I was really a kid that was 60% California and 40% Massachusetts. I was happy to be back. Be back with my dog, the sunshine and the laid back nature of life.

It was during this stage where I now had to pick a major and stick with it. I had dabbled in Linguistics, Anthropology, History, and Journalism. But anytime I went for it, the instincts of my mother kicked in so I went with Computer Science. I had racked enough credits in Journalism to be able to double major, given another semester or two, but I ended up minoring in it.

Computer Science was an interesting space for someone who loved to dress up. Everyone and I mean everyone in anything related to computers seemed to emphasize dressing down. If you dressed up or dressed ‘properly’, people viewed you as some prick who was double majoring in Business. The Business schools and the Engineering schools, within the university, seemed to have this competition between them.

During school, I picked my first official gig that applied to my major, at Barracuda Networks. A network security tech company in Campbell, California. It was here that I would dress the way I wanted, and probably more importantly in the grand scheme of things, taught me how to be a professional.

After a solid two and half years there, I picked a job at Twitter. This meant uprooting myself from the suburban areas of Silicon Valley and moving to the world's biggest little city; San Francisco.

This is when things start to pick up.

I am on my own and renting a flat in the Marina district. San Francisco is comprised of mini districts, each with its own ambience, flavour, demographic and main street. The Marina was preppy, and in a California way, reminded me of Cape Cod and Martha’s Vineyard.

It was in this flat where I would rewatch the films introduced by my dad. Over and over. But prior to that, I began watching a show called MadMen. I’m sure many of you are familiar with it. The costume designer should be showered with awards because MadMen had a profound influence on the way I started dressing. I had money now, so anything I was inspired by, I tried my very best to go out and get some variation of it. The 1950’s Manhattan look was captivating to a slightly vain mid 20’s version of me. I even dressed up as Don Draper for Halloween, two years in a row. All I had to do was pick a suit from my closet, and throw on a fedora, of which I had a couple when browsing through some of the unique boutique shops that were unique to San Francisco.

Mad Men, Don Draper, and Roger Sterling was the prelude to my genuine dissertation of the clothing worn by Steve McQueen. His style was so unique, so casually cool, that it was not an overnight affair. San Francisco was a great place to be when looking for a tweed blazer, cardigans, cable-knit sweaters, and suede chukka boots. Of course, I found the lions share of what I wanted online and my closet was making a definite transformation. I found myself in the next step. Questioning how and why Steve McQueen could pick the right time to roll up his sleeves or pop his collar. How he could wear a tweed blazer in the ’70s while playing a cop and still be a national icon and the ‘King of Cool’.

I had covered dressing properly, but now I wanted to know more before buying something. I wanted to know the fabric, the brand, and the story. I wanted some polos and henleys in Merino wool and others in cotton. I wanted my jeans, chinos, and slacks to be of the proper material for a given look I had envisioned with my mind's eye. I fell in love with tweed jackets, suede chukkas, and anything I could get my hands on that would allow me to further customize what I had now established to be proper menswear.

It was the first time that word had entered my mind. “Fine Menswear”, was the copy written on the front of a tailoring shop in the Financial District. I walked in and had a chat with the owner. We’re still friends to this day, although his business is now online and works full time at Suit Supply. I didn’t realize how much of a bummer that was until I sit here writing this.

While working full-time at Twitter, I decided to open up a recording and audio studio, to get back to my musical roots. I played the guitar, saxophone, and piano but I had no idea that this initial side business would morph into my first incorporated software company. It’s quite a story, for a different time that you can find at the Blackbird medium page, dubbed “The Mission”. It was here that I founded Blackbird Lab, Inc. Originally, Tonus. Tonus meaning ‘tune’ in Latin.

Anyways, this took me into the world of entrepreneurialism, investing, and ultimately business. In this world, all of my previous efforts in menswear would play a role. I was now the CEO and Founder of an incorporated company. I had a team to tend to, business meetings to conduct, and I had to pitch the idea and vision to luminaries in the world of venture and angel capital.

It takes an average of 2 years for a man to read about a trend or influence before adopting it.

— HandCut Radio Podcast

This whole affair brought me back down to the valley. San Francisco is a great place to find yourself, but it was littered with distractions and a labyrinth of ways you could waste your money. Especially for a complete socialite like myself with a serious case of ‘Fear of missing out’. In addition, my bank was paying a price because of the15 dollars old fashioned’s, which I had picked up from my coach and Don Draper as my defacto cocktail. I saw mixology as an ancillary extension of luxury and menswear. So I fell in love with that as well and stuffed that knowledge of the subject in an increasingly stuffed library, located in my head.

Once Blackbird was headed the right way, I decided to take on a consulting project with BoardwalkTech who were looking for a way to take new, brilliant, patented technology and create a verticalized application. The vertical we decided on was fashion and it’s ancillary players.

This was HUGE for me in my own personal world. My manager bought me every book by Rizzoli, Thames and Hudson, Bloomsbury and more. These books were written by luminaries of fashion, menswear, and womenswear. Being a man, it was the books on Tom Ford and Ralph Lauren, in addition to books written by Simon Crompton and Cameron Silver that really caught my eye.

I was immersed in these books that I would lug around in my car, which in total weighed about a thousand pounds. I discovered new brands, styles, materials, patterns, mills & factories, fine tailors and most importantly I discovered Savile Row. Having only been to the British Isle’s twice as a youngster, I hadn’t a clue about the place. This took me to podcasts like HandCut Radio featuring the likes of Patrick Grant and the founder of No Man Walks Alone.

All of these nuances influenced my purchasing decisions. I would study looks from the movies and tv series, old and new, and tie them to the stories illustrated by these menswear icons, who in my mind were in fact celebrities. They made clothes for celebrities, but I looked at it the other way around.

The craftsmanship involved was stunning, and reading about it added to the depth of my knowledge. I learned about Barbour, William-Lockie cashmere, and Porters. I now finally understood why Hermés, Dior, Hugo Boss, and Rolex were what they are.

I loved it so much, I decided to write an article, for the company, that would sort of bridge the two worlds I was living in; Software and Fashion. This article was never published because internally it was loved, and I was encouraged to write an entire book. Invoking my craft in journalism, that never went away.

A quick tangent. During my time in SF, I started a podcast & blog called the Genuine Draft San Francisco, where I would write and talk about sports. “Bay Area sports poured straight from the tap” was our tagline.

So in essence, I jumped at the chance to do what always came rather easily for me. Writing. In this book, I talked about the commonalities we all share when it comes to ‘craftsmanship’. I argued that the same amount of craftsmanship goes into building innovative software as it does for a single-breasted houndstooth blazer with a wide shoulder, waist dart seams, a round front cut, a Barchetta curved-welt pocket, a fish mouth opening, and a plain cuff.

There were chapters on people that I found had bridged the gap between business and fashion. Tom Ford, Coco Chanel, Raf Simmons, Armani and Ralph Lauren. There is even a chapter on Ian and Shep Murray, the founders of Vineyard Vines in there. All the while mentioning what was right and wrong in the world of fashion, and how our technology could right those wrongs.

After the book was printed, it became a full-on love affair. Nearly 24/7, I had on my Apple Airpods on, listening to podcasts on luxury, fashion, business and menswear.

I now had a structured way I would buy and wear things. I picked a nice scent by Hermés cologne and stuck to it. I picked which Scotch I would drink if the occasion came up. I wanted to emulate the business designer archetype that Tom Ford had created in my career, and I wanted to emulate Steve McQueen when I wasn’t at work. But at the end of the day I was still me. I had jet black hair, caramel skin and looked nothing like Steve McQueen, Tom Ford or Jon Hamm. So I had to improvise and become my own person.

After a hefty time of emulation and copying, I started to find my own distinct footing. I had found my own style, that was influenced by all these people, places and subjects I have previously mentioned. It was a special thing when I realized that I was no longer looking at images online to figure out what I would wear that day or what shirt would go good with this blazer or that jacket. I started to discern this information for myself on the spot, and this translated into how I bought. Adding one more step in my evolution in the world of menswear.

And so concludes my entry into fine menswear. If you’ve gotten this far, thank you very much for the read. Now that I’ve got my foot in the proverbial door, I’ll cover topics from wool factories in Wales, denim factories in California, tweed blazers and chukkas, the business of fashion and everything in between.

I hope you enjoyed my lengthy introduction, and I hope you stay tuned for more and remember ‘Manners Maketh Man’.


Roh Krishnan



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Roh Krishnan

Writing ‘bout beautiful things I see when I walk (browse) this incredible world. I also create products, investigate provenance, transparency, & sustainability