Can you wear a sweater vest and not look like Urkel?

For some guys, the sweater vest will always be menswear’s dodo bird. “Anything designed to keep you warm that doesn’t have sleeves is by definition a failure,” said Brook Lundy, co-founder of greeting card parody website Someecards. “On top of that, most sweater vests are just ugly. It’s just lose-lose.”

Layered under a jacket, a sweater vest can make sense—adding warmth and visual interest but not compromising the fit of the jacket’s sleeves. Worn on its own, said Mr. Lundy, it becomes unmoored, too incomplete to function as outerwear. “I need my sweaters to do some heavy-lifting,” he added.

Worse, sleeveless sweaters have been tainted by unfortunate associations. From your junior-high science teacher to the taunted nerds of TV’s teen comedies, sweater vests, with their baggy silhouettes and argyle prints, telegraph schlubbiness.

“That’s too bad,” said DJ and entrepreneur Brendan Fallis. “If André 3000 wore a sweater vest, you’d be, like, that’s pretty dope.” (Note: He has and looked reasonably dope.) Mr. Fallis also cites the sweater vest’s sad history as a golfer cliché. He gravitates toward “really thin cashmere, V-neck sweaters” with fully realized sleeves.

Asked if he opposed all vests, Mr. Fallis confessed a fondness for the puffy down variety come fall. But as for sleeveless knits, he was resolute: “You should just wear a full sweater!”

Custom Sweaters By Tom James

If you hear Urkel wondering, “Did I do that?” every time you see a sweater vest, we can’t blame you. But recently the forlorn knit has been enjoying a resurgence, celebrated by both runway darlings like Gucci and stalwart brands like the U.K.’s John Smedley.

“To me, a sweater vest was almost a sign of giving up,” said recent convert Josh Peskowitz, co-founder of menswear shop Magasin, in Los Angeles. He was convinced by a button-front mohair style, from Italy’s Massimo Alba. When he fastened it over a T-shirt, he recalled, it suddenly “felt so subversive and cool.” Those familiar with the mysterious fashion principle “so out, it’s in” will understand.

Many sweater-vest enthusiasts, like Mark Cho, co-founder of Hong Kong and New York haberdasher the Armoury, still value the style most as something to slip under a jacket or a suit. Mr. Cho said he often steers suit-wearing customers toward a navy button-up style first, since it mimics a traditional waistcoat.

Some rules to follow if you’re sporting a sweater vest without a coat: To avoid the dreaded blouse-y look, make sure both it and the shirt underneath are fitted. Roll your sleeves to counteract the sweater’s fusty image. And finally, to ward off Urkel associations, spurn patterns and stick to solid colors.