Q&A with Oliver Cheshire

We talk to Oliver Cheshire, as he swaps the catwalk for Cowes Week with team HUGO BOSS and British skipper Alex Thomson.

Tell us how this partnership arose…, I did a shoot in New York with Hugo Boss a few months ago, which went really well and that led to this incredible opportunity. When they approached me, I said ‘100% yes’!

What attracted you to take on this challenge?, I’ve seen and read lots about Alex Thomson and the “HUGO BOSS” yacht, which sparked an interest with me. I was really intrigued and just couldn’t say no to the opportunity!

What attracted you to the charity?, Great Ormond Street is an amazing hospital. I have lots of children in my family, I was ill when I was young, and my sister’s little boy has had problems – so I really wanted to choose that hospital.

What have you done to prepare for the race?, Put on some fake tan (haha!)…

No really, I did lots of research into the team, the “HUGO BOSS” and the collaboration with Hugo Boss – and I scrubbed up on some sailing words.

What words do you know now?, Port… starboard…. grind…

Actually, on the day it was more like: someone points… someone swears… and then shouts “DO IT!”… That’s the extent of it!

Up until today what has been your previous sailing experience?, I’ve been on a few paddle boards, and been invited on to my boss’ boat in the Mediterranean.

Of all the celebrities that have contributed to the HUGO BOSS race, who do you want to beat the most?, Ewan McGregor would be cool to beat! He is an amazing actor. I would like to beat Douglas [Booth] as well as I know him personally.

If you could sail to any destination in the world where would you choose and who would you bring along?, I would obviously take Pixie [Lott], my girlfriend, and would like to sail to the Bahamas – I have never been there. Let’s get some sun!

How did you find the transition from modelling in a studio to competitive sailing on a yacht? Did you feel out of your comfort zone?, I felt massively out of my comfort zone! The two environments are so completely different. Actually, Alex [Thomson] mentioned that when he puts on a suit he doesn’t feel comfortable, as opposed to when he is in his sailing gear. I am the complete opposite, but I absolutely loved it and would 100% do it again.

What have you learned from Alex today – did he give you any advice?, Be focused, and hold on tight. There is so much happening on the boat at the same time – it can be dangerous so you have to remain focused. I could see the concentration on Alex’s face – it was amazing to watch.

What makes a man a gentleman?, Manners – saying “Please” and “Thank You”. Also, dressing well and being presentable at every occasion.