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.
M. CARTER
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.”
—Milton Carter
LOLA
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.’”
—James Cruickshank
BARKING IRONS
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.”
—Michael Casarella
KENZO MINAMI
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.”
—Kenzo Minami
YOKO DEVEREAUX
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.”
—Andy Salzer