Flashy & Fabulous

In watches, "chunky" is a good thing for flash and dash, and this $1,695 Serein Diamond by Michele is "strictly designed to be seen," says Lindsay, with a 40 mm diameter case, stainless steel and two-tone rose gold plate, seven-link bracelet. The Roman numerals and 100 diamond-bezel are a nod to tradition and sophistication.

Always Time for Love

Delicate & Dressy

More of a bracelet than a gadget-packed timepiece, this $325 Lovely from Tissot with an everyday, feminine profile gets lots of polish and sparkle from a stainless steel bracelet and 37 Top Wesselton diamonds around a dainty 19 mm diameter case.

Elegant in Alligator

Designed by a woman "” for women. "It will easily float between everyday and dress wear," says Lindsay. The $6,600 Princess Grace by Mont Blanc features a stainless steel case with a gently elongated shape trimmed with diamond-set flange, elegant Breuguet numerals with a drop-cut pink sapphire at 6 o'clock and an alligator band.

Weekend or Work

The Swiss-made Hamilton line is based on old American heritage watches "” think traditional military aviation watches from the "¢70s. The $535 Pilot Pioneer "is a fun, weekend kind of watch that can easily go to work as well," says Lindsay, with brushed stainless steel finish, purple/orange/black nylon strapping, two asymmetric counters and Superluminova hands.

Regatta-Ready

You hardly need this on the Ohio River, but this stainless steel and Everose gold creation "” the $25,150 Yacht-Master II by Rolex "” is "the most complicated watch to date," says Lindsay, boasting programmable regatta countdown with mechanical memory and a paramagnetic blue Parachrom hairspring oscillator. And it's waterproof to 330 feet. "It's definitely a niche watch and falls into the collector's realm," adds Lindsay. At 44 mm, it's the biggest watch that Rolex makes.

Sleek & Tailored

From one of the oldest watch companies, this $3,800 Omega de Ville Prestige is "the quintessential men's dress watch," says Lindsay, "set thin so you want the casing to be subdued." Men's dress watches almost always have a leather strap "” this one is alligator. The face is sleek and tailored with a small seconds hand and a domed, scratch-resistant sapphire crystal and black dial.