17 questions to a well-dressed man – Ash Happyman
I think few people would question whether London is the cradle of classic menswear. It is a city that has shaped the way we think about traditional men’s clothing and has inspired tailors, shirtmakers and designers around the world. Even today, London is home to some of the finest names in bespoke tailoring and shirtmaking.
One of them is Mayfair & Legacy, which continues to produce bespoke shirts in the UK using some of the finest fabrics available. Its owner, Ash Happyman, is not only a true gentleman but also someone who inspires his customers through the way he dresses himself.
For that reason, I thought Ash would be a perfect addition to my “17 Questions to a Well-Dressed Man” interview series. I was delighted when he agreed to answer my questions, giving us a glimpse into his personal style, passions and tastes.
So, without further ado, let me introduce you to Ash Happyman. I hope you enjoy reading our conversation.
What are you wearing today?
I’m wearing a striped shirt from Mayfair & Legacy. I’ve paired it with navy wool trousers and a white cotton double-breasted jacket, finished with navy suede Belgian loafers. For accessories, I’m wearing a navy paisley silk tie and a very personal pocket square.
I’d love to share the story behind this pocket square: during my last trunk show in Washington, D.C., I visited the U.S. Capitol Building and was mesmerised by The Apotheosis of Washington painted across the ceiling dome. Upon returning to the UK, I had that exact artwork printed onto silk twill with hand-rolled edges. Today, I’m wearing a piece of art right in my chest pocket.
If you had to choose to spend money either on a suit or on a watch, what would you choose?
It’s a very complicated question because I love both! But if I were spending a significant sum, I would choose a watch.
What jewellery could a man wear?
For a married man, a beautiful wedding band is essential, alongside a fine watch, of course. I’d also recommend a subtle bracelet, it adds a great finishing detail to a man’s wrist.
Tie or a bowtie?
I am definitively a tie person. I love wearing ties even casually with jeans, and I’m always collecting them. However, every man should own a couple of bowties, specifically in black or navy, for tuxedos. Crucially, it must be a self-tie; a pre-tied bowtie will ruin your entire outfit!
Do you remember your first jacket?
The first jacket I bought for myself was an off-the-rack navy suit for my graduation.
What is your favourite watch?
My current favourite is a vintage Omega that I recently sourced from Japan. It features a small gold case paired with a green leather strap, which sits perfectly on my wrist. As for my dream piece, I am actively searching for a vintage Tank Louis Cartier in great condition.
Fountain pen or ballpoint?
Fountain pen, always. I love collecting beautifully made fountain pens, they are a miniature form of engineering you can carry with you, and writing with them feels like a wonderful ritual.
Have you found the perfect garment yet?
I think I am perpetually searching for it! It’s a continuous journey of trial, error, and refinement.
Explain your biggest passion in one sentence?
I have a deep passion for cars and driving; one of my ultimate dreams is driving an Aston Martin on a quiet morning on the way to my atelier.
What is your guilty pleasure?
Collecting scale model cars, I spend a good amount on them, and I’m fast running out of space to display them!
Who is the best dressed man in the world for you?
Rather than a real person, I am deeply inspired by a character: James Bond. I am a big fan of the films, and whether it’s Sean Connery or Daniel Craig, the tailoring has always helped shape my personal style.
On a personal level, my father was the best-dressed man I knew. He always took pride in his appearance and taught me that dressing well is about self-respect, even when times are tough.
The best book you ever read?
The best one is yet to come!
Which city should one go shopping?
London, above all—simply because I know every corner of it and where to find true quality. Outside of the UK, I love shopping in Florence and Milan. I love window shopping more than real shopping!
Tweed or flannel?
I love tweed in general, but I am a much bigger fan of flannel. I just love the texture, feel, and drape.
The most elegant restaurant in the world for you?
Bacchanalia on Mount Street in London. I love the ambiance and visual grandeur even more than the food.
Describe your style in three words?
Tailored. Timeless and appropriate
Best purchase you did in the last 6 months?
I recently brought home a puppy. More than any luxury purchase, he has brought me the most joy, and it’s my first dog .