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.