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A Conversation With Mr. Leonardo Simoncini

This story originally appeared on the Gents Cafe Newsletter. You can subscribe here.


Meet Leonardo Simoncini (@leonardosimoncini), a tailor based in Florence, Italy who learned the craft at Liverano and now runs his own tailoring house.

2. How do you define your style?

I like to wear tailored garments, of course, but vintage and even “basic” elements also come into play. I want to keep my style as personal as possible, without forcing it towards formality just because of my job. For example, one of my most treasured possessions is a US Army jacket, originally belonged to my grandfather and later handed down to my uncle, my father, and eventually me.

3. What does it mean for you to be a Modern Gentleman?

Being a gentleman to me means being polite, respectful to others, and avoiding any kind of judgment. In general, I believe it’s important to be the best version of yourself, rather than just conforming to etiquette. There’s no point in knowing manners if that’s just to “show off” your status.

4. When it comes to style, where do you mostly get your inspiration from?

I don’t have a specific style icon that I look up to: I get my inspiration almost everywhere, from social media, magazines, old pictures, sometimes even just from a person walking in the street. I usually tend to spot unexpected combinations of garments rather than entire outfits, and then try to replicate them on myself.

5. What’s your personal style signifier?

Right now, what defines my style are mostly high-waisted, pleated and wide-leg trousers. I’ve been paying a lot of attention to trousers lately, because I think they are the most interesting garment in tailoring, and I would like to create my own line in the near future.

6. What are your favorite wardrobe essentials?

Sport jackets, jeans, tassel loafers and ulster coats: they are all versatile pieces, that work well paired to formal tailoring but also dressed down with a t-shirt or a button down Oxford.

7. What are your main passions and how do you cultivate them?

Sport is a big passion of mine: I regularly practice football, tennis, and kitesurf; also, I’m often at the gym. Besides this, I love going to flea markets hunting for vintage stuff, especially old fabrics: I have more than 600 in my personal archive, from some of the oldest and most famous mills around Europe.

8. What does your ideal Sunday look like?

My ideal Sunday starts with a slow morning, having breakfast at home or in a bar (I love Bottega di Pasticceria along the river Arno), followed by a drive in the countryside or to the seaside. I love the area around Bolgheri: good wine, beautiful countryside and close enough to my beloved beaches of Viareggio and Livorno.

9. Describe an interesting trip you have taken and tell us what’s the next destination on your bucket list.

I got the chance to visit Japan a couple of years ago, and I found the country absolutely special – profoundly different from the West and its culture but deeply fascinating at the same time. For this same reason, since I’d like to get in touch with the Asian world, I’ve booked a flight to Hanoi, and I will travel through Vietnam, Cambodia and Thailand.

10. Tell us what can never be missing in your liquor cabinet.

I’m not a huge expert on liquors or mixology in general, but I can tell you that a good bottle of red wine is never missing at home. I’ll never say no to a nice Bolgheri.

11. What are your three favorite books?

The Craftsman by Richard Sennet, The Kite Runner by Khaled Hosseini and Tales from Ovid by Ted Hughes.

12. What are your three favorite movies?

The Best Offer by Giuseppe Tornatore, Gone Girl by David Fincher and Romeo + Juliet by Baz Luhrmann.