Gorgeous wool flannels, brisk tweeds, soft knit cashmeres—just the sort of warming fabrics one wants in wintry months, except they leave the arms bare. It is one of the great curiosities of fashion: Women want more sleeves, and designers love to make dresses without them.

This tension results in an awkward routine each season. Store buyers prowl showrooms in search of dresses with sleeves. Designers never seem to make enough. “There’s a lot of screaming and yelling to get more sleeves in the market,” concedes designer Nanette Lepore.

Yuta Powell, owner of the Yuta Powell boutique on East 75th Street in Manhattan, takes things into her own hands. Two finely tailored gray wool flannel jumpsuits hang in her store now this week. One is a fall 2014 runway look from Paris-based designer Pascal Millet. It is sleeveless.

The other jumpsuit is one Ms. Powell asked Mr. Millet to doctor. Its graceful sleeves veer out at the elbow and fold back—a flattering, nonchalant-looking design she learned years ago while working for Hubert de Givenchy.

Ms. Powell isn’t shy about asking designers to add sleeves when she places orders. She even offers them sketches to work from. “I’m the one that has to sell it to the customer,” she says. “If I had to rely on what they think the client wants, I’d have to eat it.”

To designers, sleeves can be frumpy. They also pose design challenges. Sleeve peeves may be rising in part because it is so tricky to make a flattering sleeve that is roomy enough to offer a full range of motion. With more casual styles and the introduction of stretch fabrics from denim to silk, women have grown accustomed to comfort, and they are more likely to revolt against constrictive clothing.

“In the past, the tolerance for uncomfortable clothing was a lot higher than it is now,” says designer Trina Turk.