Photograph by Nick Veasey/Getty Images
If the idea of having your underwear made to measure makes you squirm, most men would likely agree. Fact is, underwear doesn't really need to be customized. Since waist sizes must be flexible to handle expanding stomachs after big meals, boxer shorts and even briefs don't need to be perfectly fitted. If you do want something special, make sure the boxer is made of silk or cotton with a yarn number of more than 100 (which makes the material smoother). Or you can buy briefs or boxers made by the Swiss company Zimmerli and have them specially colored for you by Kabbaz Kelly & Sons in New York. When it comes to boxers, that may be bespoke enough.
$440: Zimmerli boxers made in Switzerland ($55 each for eight pairs) -- Kabbaz Kelly & Sons
Running Tally: $22,295