Power dressing: Gary Gregory

Gary Gregory, 59, is founder of Sirius Software and a board member of National Grand Bank. He also owns the Valiant, an America’s Cup yacht.

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Jacket by Canali

This is a charcoal plaid wool sports coat with a touch of pink. Today I have a board meeting, which is always a jacket day.

www.canali.it

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Dress shirt by Eton

Normally I wear a lot of white shirts. Today I’m branching out. I’ve been going to these board meetings twice a month for 10 years so I’m much more comfortable with these folks. And pink lets you wear a more exciting tie.

www.etonshirts.co.uk

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Tie by Robert Talbott

This is black silk with a muted pink/burgundy stripe with grey checks. Dressing for board meetings and customers, you want to be more conventional. As it gets closer to Christmas my ties get crazier. It’s the only time of the year you can wear crazy ties.

www.roberttalbott.com

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Trousers by Ballin

These are tailored black wool slacks. On more casual days I wear more earth tones but with this outfit the message I’m sending is that “my meeting with you is important enough that I didn’t want to guess wrong and be under-dressed”. Black pulls it back to conservative.

www.ballin.com

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Shoes by Bruno Magli

I like the traditional clean style of Bruno Magli. For short trips I wear the loafers because they are easier at airport security checkpoints.

www.brunomagli.it

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Watch by Panerai

This is the Luminor GMT. My interest in Panerai came from the sailing races. I had met the president of Panerai at a regatta and he was talking about how watches are the only jewellery outdoorsy men will wear. So when they find an outlet for that fashion they go nuts. This label started the big dial watch as a diving thing; to read it underwater you need a dial almost cartoonish in size.

www.panerai.com