1. RICHARD SIMMONS SHORTS
Retro athletic shorts with stripes or piping.
Runway: Jean Paul Gaultier, $365 at Tobaldi, 83 Rivington St., at Orchard St.; 212-260-4330.
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. New Balance shorts, $35 at JackRabbit Sports, 42 W. 14th St., nr. Sixth Ave.; 212-727-2980.
2. FLASHER SHORTS
A manner of dressing that intentionally reveals boxers.
Runway: Michael Bastian, $430 at Bergdorf Goodman Men’s, 745 Fifth Ave., at 58th St.; 212-753-7300.
Reality: Khaki shorts are always a safe bet. But exposed boxers are best left to teenage boys at summer camp. Shorts, $39.50 at Banana Republic, 528 Broadway, at Spring St.; 212-334-3034; and boxers, $25 at Brooks Brothers, 346 Madison Ave., at 44th St.; 212-682-8800.
3. AMPUTATED TROUSERS
Knee-length shorts that resemble cutoff dress pants.
Runway: Calvin Klein, $375 at Calvin Klein, 654 Madison Ave., at 60th St.; 212-292-9000.
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. Trousers, $110 at J. Press, 7 E. 44th St., nr. Fifth Ave.; 212-687-7642.
4. DENIM CUTOFFS
The menswear analog of the Daisy Duke short.
Runway: Dsquared, $375 at Saks Fifth Avenue, 611 Fifth Ave., at 50th St.; 212-753-4000.
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. Levi’s cutoffs, $48 at Macy’s, 151 W. 34th St., at Broadway; 212-695-4400.
5. SHORT SHORTS
Any style with an inseam of four inches or less.
Runway: Prada, $285 at Prada, 575 Broadway, at Prince St.; 212-334-8888.
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. Lorenzini boxers, $195 for a three-pack at Barneys New York, 660 Madison Ave., at 61st St.; 212-826-8900.
Designer: Milton Carter, 31
HQ: Greenpoint, Brooklyn; $60 at Dernier Cri, 869 Washington St., nr. 13th St.; 212-242-6061.
What is this? “The tea set on this shirt suggests the upper class as well as history, the past. It says classy and trashy at the same time.”
Designers: James Cruickshank, 23, and Emmett Shine, 23
HQ: Lower East Side; $45 at Charlotte Ronson, 239 Mulberry St., nr. Prince St.; 212-625-9074.
What is this? “Instead of the standard ‘New York, London, Tokyo, Milan’ tagline used by fashion houses, we say, ‘New York, New York, New York.’”
Designers: Daniel Casarella, 29, and Michael Casarella, 24
HQ: The Bowery; $70 at Bloomingdale’s, 1000 Third Ave., at 59th St.; 212-705-2000.
What is this? “‘Bean Soup’ refers to the nickname of an old New York City fire truck. There is something very Popeye about it.”
Designer: Kenzo Minami, 33
HQ: Lower East Side; $175 at Barneys New York, 660 Madison Ave., at 61st St.; 212-826-8900.
What is this? “This particular T-shirt is inspired by the million-mark banknote in the time of hyperinflation in 1923 Germany.”
Designer: Andy Salzer, 34
HQ: South Williamsburg, Brooklyn; $70 at Yoko Devereaux, 338 Broadway, nr. Keap St.; 718-302-1450.
What is this? “Jewelry, in many instances, comes off as costumey on guys. On a tee, it is much more masculine.”