Broken-in original suede Sperry Top-Siders
The first place to start when putting together a stylish, yet comfortable, warm-weather outfit is an ace pair of lightweight kicks. Step forward, timeless Sperry Top-Sider! ($78 from Jcrew.com)
Lauren by Ralph Lauren Blue White Gingham Vest
This dapper vest is perfect for sipping cocktails -- and romancing summer-frocked ladies -- on long, warm evenings. ($60 from Macys.com)
Relic Stainless Steel Pocket Watch
If you are going to sport one dandy-ish affectation this summer, make it a silver pocket watch. ($55 from Kohls.com)
Calvin Klein Benjamin Flat-Front Pant With Clean Finish
Every gent needs a smart pair of summer slacks. This crisp pewter-colored pair from Calvin Klein fit the bill nicely. ($25 from Macys.com)

Alaska Cruise
Sure you have to give up that I've-just-been-on-a-cruise tan but taking in the wonders of the rugged Alaskan landscape is worth packing a scarf for. From the whales to the glaciers, you probably want to catch them while you still can. (From $350 for seven nights)