• SumoMe

Shorts should only be worn in super-casual situations, and if you’re going to do it, do it right. Sticking with a few cardinal rules will get you far in the short world: no pleats, no plaid, and no cargo side pockets. Stray from these rules only with the utmost care and awareness.


Gap 1969 Roll Up Brooks Brothers Whale Bonobos Chambreros Lands’ End Chino
For the most casual
of short days, try
these roll-ups instead
of those cutoffs.
Wear these “go to hell”
shorts with caution: no
patterned shirts, and
no belt free days.
Light fabric shorts are
great for hot days, and
these should even pair
well with tennis shoes.
A heavier fabric, but
nice with a chambray
shirt–stick with some
brogues or chukkas.

 Which of these is your favorite? Any suggestions on wearing shorts well? Give your advice in the comments below.