11 Burning Questions About Men’s Shorts, Answered

6 Inches: Just Right, Goldilocks

Just above the knee is where you want to be. In inseam terms, that’s anywhere from 4.5 inches, for the vertically challenged, to 7.75 inches for taller sorts. “You don’t ever want to go too close to anything that’s below the knee,” said Jonathan Eyal, the owner of Supply & Advise boutique in Miami, a shorts town if there ever was one.

10 Inches: Juvenile

Bypass three-quarter-length boardshorts, dangling basketball bloomers and anything that even borders on capri territory. “Especially with shorter guys, you can’t go too long,” said Mr. Eyal. “It messes with people’s proportions, and it looks really childish.” Before you start strenuously arguing why your calves must be covered, may we interrupt you and recommend jeans?

2. I’ve had the same three go-to pairs of khaki cotton shorts since college. How do I upgrade from beige?

• C. Yes, this unicorn exists. Here, glen plaid evokes your favorite blazer. Z Zegna Shorts, $255, Ermenegildo Zegna, 212-421-4488

3. Can I wear cargo shorts without looking like a 16-year-old?

Oh, the contentious cargo shorts: While some men cherish their practicality, others would like to see those bulky pockets filled with dynamite and blown into oblivion. Both sides have persuasive points to make, but, said Mr. Pask, "You can’t dismiss cargo shorts categorically.” When the pockets are too protuberant, too saggy, cargoes can look ungainly, but they can also be slender and, dare we say, rakish. Brands from Uniqlo to Brunello Cucinelli produce nipped cargoes with just-large-enough pockets. And extra storage at your thighs matters more than ever: "People are dragging around their phones, they’re dragging around their charging cables, [the pockets] are a good place to keep things," said Mr. Eyal.

4. Where can I wear shorts?

• Brunch
• A tense croquet showdown
• A 2-year-old’s birthday party (in July, not January)
• A date night on vacation
• A baseball game (as spectator or starting shortstop)
• The office, if you are a park ranger and your office is a park

5. Where can’t I wear shorts?

• A funeral
• Court
• The theater
• A job interview
• A parent-teacher conference
• To meet the in-laws
• A televised debate
• The office, if you are not a park ranger and your office is not a park

6. Why does Prince George relentlessly wear shorts?

“It’s part of this idea of there being a firm division between early childhood and wearing more adult clothing as you grow older,” said Carolyn Harris, author of “Raising Royalty, 1000 Years of Royal Parenting.” Like all princes before him, Prince George, the floppy haired scion of Britain’s king-to-be, wears shorts in an aristocratic tradition dating back to the 18th century (see #7).

7. Who was the first man to wear shorts?

He remains unidentified, but according to Mark-Evan Blackman, a professor of menswear at New York’s Fashion Institute of Technology, shorts have their origins in breeches, modeled here by “The Blue Boy,” painted by Thomas Gainsborough. In the late 18th century, European families clad their youngsters in these three-quarter-ish length pants that were supposedly easier to take on and off during potty-training. In wealthy families, the kids would graduate to longer pants around age 8; poorer youngsters would languish in their proto-capris while working the fields, selling newspapers or generally being embarrassed. The modern, above-the-knee, cotton short was birthed by British soldiers in colonial India, inspired by that country’s traditional lungi wraps for men.

8. Should I tuck my shirt into my shorts?

If your shirt is a T-shirt, never. Squeezing a T-shirt into your shorts because you’re feeling too informal looks incongruous and a little dweeby. The same goes for a polo shirt—tucking in a preppy piqué polo reads too country-club fussy. The one shirt you should consider tucking in is the button-up shirt. While you can keep those nonchalant tails hanging out for more beachy events, secure them into the waistband for any event with a silent auction component or lunch at a restaurant with the word “Chez.” If you do tuck, be cautious of your belt choice: A shiny leather dress belt is too corporate, while anything ribboned or stitched with cutesy whales is best left on Nantucket. The safe bet: A braided leather belt, preferably in a solid, seasonally light color.

9. Is the ’shorts suit’ really a thing?

It’s certainly trying hard to be. The shorts suit has been promoted by designer Thom Browne (right) who wears his year-round and has been sending $3,000-ish versions down the runway for over a decade. Pharrell Williams likes them, too. But should you try one? Perhaps unnecessarily, we’d urge caution: It’s too eccentric and distracting for everyday wear. Still, there’s nothing wrong with slipping on a sportcoat atop shorts—a summery sartorial statement that won’t set you back $3K. “You can take any short, throw it with a casual to dressier jacket and all of a sudden you have your evening look pulled together,” said Mr. Pask, who while on vacation recently elevated his Dries Van Noten shorts for dinner by tossing on a blazer. The mismatch makes the combo casual: “It feels much less considered and more casual to mismatch a jacket and a short.”

10. I have a pair of turtle-emblazoned “critter shorts” that are my favorite item to rock in the summer. I bought them in Nantucket six years ago and it was the best summer of my life: I caught a giant swordfish while wearing them and won at beer pong. The only problem is, my wife thinks they’re lame. So please settle this debate: Are critter shorts timeless or passe?

Sorry, your wife is right. No critters.

11. I wear jeans all winter, so is it cool to wear “jorts” (aka jean shorts) in summer?

No. Unless you’re Andre Agassi in 1988 at the French Open. And even then—no.