Sir Paul Smith might be fashion's biggest cycling fan. Long before he took up tailoring, Smith raced bikes, as a teenager in Nottingham, England. Though his competitive career ended early, after a bad accident when he was 16, his enthusiasm for the sport never wavered. A lover of cycling design, Smith has collaborated with Rapha on clothing and with Mercian on a limited line of cycles. Here, he offers sartorial tips for city cyclists. When did you first fall in love with cycling? When I was 11, my dad bought me a pale blue Paramount bicycle. The man he bought it from was a member of the Beeston Road Club. The man suggested that if I wanted to join some of the club riders on a Sunday for a ride, he would make sure I was O.K. I joined the club and slowly started to understand the world of cycling and especially racing. At the age of 12, I rode my first race as a schoolboy and got completely hooked on the competitive spirit, the teamwork and of course something called the Tour de France and all the great riders, like Jacques Anquetil and Fausto Coppi. Have any of your clothing designs been inspired by cycling? Over the years, many times. Especially the projects we did for the cycling company Rapha. How many bicycles do you own, and what kind? I have several Mercian bikes. Mercian is a 66-year-old company, and they still make handmade bikes - with a staff of only nine! I also have a Pinarello given to me by Team Sky; a Condor given to me by Condor; a Danish town bike; a bike I designed for a Danish cancer charity made by Principia; and, at my home in Italy, Bradley Wiggins's old race bike, made by Giant. What makes for the best city bike? For me, a classic bike without dropped handlebars. The Dutch and Danish brands are normally perfect. What sartorial tips might you offer to the urban cyclist? This depends solely on what your profession and lifestyle are. If you cycle to work and can change clothes when you arrive, classic cycling clothing is perfect: windproof, breathable, waterproof. Of course, I am biased towards the Rapha brand. If you are cycling in regular clothes, carry a lightweight waterproof jacket for that sudden shower and some form of high-visibility clothing or accessory for safety. How should New York's commuting cyclists keep warm in winter? Lots of layers, with the outer layer being windproof, waterproof, breathable and with lots of pockets. What about trouser length? From a fashion point of view, the trend right now is for short, cropped trousers, and this also works for the bike. Any particular socks? Rapha's Merino socks are great, as they are made in a heavier yarn for increased insulation. Do you have a favorite kind of helmet? I always wear a Giro helmet. What about bags? Do you have a favorite shape or design? Any backpack or cross-body bag will do. What materials were cycling kits made of when you used to race, and how have they changed over time? They initially used to be made with lightweight merino wool, which of course was difficult when wet as they got very heavy. Then they changed to rayon, which was a lot better. Of course today's kits work really well, but visually I prefer the original merino wool with with buttons and a collar - very cool. Cycling jerseys are subject to their own fashion trends. Leopard-Trek seems to be leading a movement toward a very simple, almost old-fashioned aesthetic, while Footon-Servetto jerseys have been heavily criticized for adopting a busier look. What dictates these shifts? One of the big issues is the amount of advertising and sponsorship that you have to get on a jersey, and company logos related to the sponsor, which can often be in inappropriate colors. The simplicity of Rapha's jerseys is great, and, yes, I do like the Leopard-Trek jersey. Which pro team has the best jerseys? I'm not sure about worldwide, but the U.K. Rapha pro team jersey is really great, followed closely by the new Sky Team jersey. Who is the best-dressed person in cycling? On and off the bike, Bradley Wiggins takes some beating. He's a very good Paul Smith customer, so I'm biased. Where is your all-time favorite ride? Anywhere in Tuscany.