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Step 1: Rethink the accessories

TIES — A thin tie adds a hip, retro look. Think of ’60s Italian hipsters roaming the Amalfi Coast in “The Talented Mr. Ripley.” Not too skinny, though; ’80s New Wave is Old Wave. Neil Barrett tie, $175, at Neiman Marcus.

CUFFLINKS — Keep the bling to a minimum, but this is a great area to let go and have some fun. Fornasetti sterling silver “Eye” cufflinks, $395, at Barneys New York, Chicago.

SHOES — Dress tennis shoes can go a long way in relaxing the look. But keep them clean; these aren’t for sports, sport. Adidas “Universal” sport shoes in suede and leather, $75, at Barneys New York, Chicago.

Tom Ford gray three-piece suit (shown without vest), $4,660, and lilac cotton shirt with contrasting white collar, $390, at Tom Ford, NYC. Dolce & Gabbana worsted wool tie, $135, at Neiman Marcus. Lanvin onyx tie pin, $150, and onyx cufflinks, $320, at Barneys New York, Chicago.

Mr. Rittenhouse on keeping his body lean and mean.

I train with kettlebells. They keep me lean. They have been around in Russia for about 300 years and resemble an iron cannonball with a handle welded onto it.

Ever heard of the ‘one-armed kettlebell snatch’? (Laughs.) You swing the kettlebell with one arm up over your head with momentum–it burns a ton of calories.

I never count calories. If I do, I get obsessed with the numbers. I become a compulsive calorie counter, and that’s not fun.

I take fish oil every day. I find it helps in weight management.

‘Protein intensive’ is how I describe my diet. I eat a lot of egg whites, and I’m not much of a drinker.

If I go more than a week without exercise, I get depressed. My body is hooked.

I don’t expect the women I date to have the same passion for working out as I do. I’m not obsessive about women’s bodies. It’s just not an issue–I’m never harping in my date’s ear about not having a glass of wine or dessert or anything like that.

–Lisa Cregan

Step 2: Lose the pants

Well, not literally. Keep the vest and jacket, but replace the trousers with jeans. Go with dark, straight-leg salvage jeans. Urban, edgy, a little rock ‘n’ roll.

Alexander McQueen wool one-button jacket, $1,150, and slim denim trousers, $380, at George Greene, Chicago. Bottega Veneta gray melange wool vest, $580, at Bottega Veneta, Chicago. Club Monaco cotton pinstripe shirt, $89, at Club Monaco, Chicago. Banana Republic cashmere cap, $60, at Banana Republic, Chicago.

Step 3: Let bright colors do the heavy lifting

Leave the jacket at home and add a splash of color with a V-neck to loosen up the look. If you want to wear your shirt untucked and not look sloppy, buy slim-fit dress shirts with a square cut along the bottom. The cleaner line lets you be untucked but still look crisp and pulled together. Think Preppy Handbook with a twist.

Lanvin wool plum V-neck sweater, $1,150, and white shirt with silk satin collar $480, at Barneys New York, Chicago. Tom Ford wool jacket and trousers, as before.