How to wear shorts, plus the of-the-moment T-shirts to wear on top.

1. RICHARD SIMMONS SHORTS

Retro athletic shorts with stripes or piping.
Runway: Jean Paul Gaultier, $365 at Tobaldi.
Reality: Limit the wearing of these to actual athletic events. Swap them for the baggy basketball trunks in your gym bag—medium-length shorts with stripes are a good compromise of function and gym-appropriate sexiness.

2. FLASHER SHORTS

A manner of dressing that intentionally reveals boxers.
Runway: Michael Bastian, $430 at Bergdorf Goodman Men’s.
Reality: Khaki shorts are always a safe bet. But exposed boxers are best left to teenage boys at summer camp.

3. AMPUTATED TROUSERS

Knee-length shorts that resemble cutoff dress pants.
Runway: Calvin Klein, $375 at Calvin Klein.
Reality: These creased shorts, a stylish twist on Bermuda shorts, come close to office-appropriate. But probably not close enough. Make your own with scissors, as we did.

4. DENIM CUTOFFS

The menswear analog of the Daisy Duke short.
Runway: Dsquared, $375 at Saks.
Reality: Formerly an icon of lowbrow taste, denim shorts have regained traction. Their fit should be trim to the thigh and the fabric dyed dark; always go sockless.

5. SHORT SHORTS

Any style with an inseam of four inches or less.
Runway: Prada, $285 at Prada.
Reality: Men who wish they were taller love abbreviated shorts because they make legs appear less stubby. Nevertheless, it’s best to restrict their use to vacations, when tanned limbs help make a case for skimpiness. In most other circumstances, short shorts are underwear.