Is anything still cool in fashion?

And in fashion, that new cool has been ushered in by Willy Chavarria. This guy is cool — and, more importantly, so is his clothing. The designer, who’s in his mid-50s, spent his career in the commercial trenches at brands such as Ralph Lauren and Calvin Klein while nurturing his own label. The energy around his brand has been spiking for the past few years — and he won the CFDA’s American menswear designer of the year award last fall — but this show felt like a true arrival. A true thesis of cool: guys in beefy leather jackets and carrot-leg pants, collars as long and pointy as an index finger jabbed in your face, coats with lapels in “we mean business” size. After walking the runway, the models stood behind a long table covered in dripping candles — very pious, as if those who wear Chavarria aren’t merely wearing clothes, but yanking fashion toward a higher purpose.

Part of Chavarria’s cool comes from his age: He’s decades older than designers are when they typically have their moment. He doesn’t have to worry about trends; he’s past the point of beating his chest about what older generations don’t understand. He can just be himself. He has ease; he’s self-deprecating: “I care more about film than I care about fashion,” he said after the show with a shrug, to explain his decision to begin the show with a brief cinematic effort. He said he wanted to make his clothes more commercial this season — laughing, because that sort of bold declaration is considered a sin, even though it’s what you need to survive.

But the real seed of Chavarria’s cool is his vision of masculinity: I have never been so moved by a short man in a big hat, and really, nothing says “American style” like a man who cares gingerly for his favorite sweatsuit. These are men whose lives are ruled by competing urges: outrageous insecurity and the instinct for flamboyance. Rare is the designer who views this kind of inner turmoil with such tenderness.

That feeling of cool, of ease and confidence and empathy, threw two other shows into relief: Khaite, by Catherine Holstein, and Peter Do’s Helmut Lang.

Holstein staged her show Saturday night in a pitch-black room with a shiny runway. The setting and collection were too serious and stiff. Like with more baldly influencer-adjacent brands, she is held hostage by oversize silhouettes, and her fabrics (leather, or silk bunched into a cloudlike form) and sense of proportion make her women look so droopy. They are clothes designed for a great night out, at least as the styling and staging would suggest, but their heaviness would get in the way of a good time. Oversize clothing can make a woman look nonchalant, but too-oversize clothing makes her look disempowered. Why is a woman wearing a comically huge leather anorak over a bunched gown, and why in the world is she in such a hurry? These clothes felt disconnected from reality.

Sharp. Witty. Thoughtful. Sign up for the Style Memo newsletter.

That lack of real-world action is what has Do’s Helmut Lang stuck in the old cool, as well: It lacks the transportive finesse of his eponymous brand’s language, which can seduce you into wearing a severe black suit, and the down-and-dirty ’tude you want from an “accessibly” priced label, like his Lang is meant to be. His bubble-wrap pieces feel more likely to be worn by an unserious SoundCloud rapper than an elegant artist or a 20-something cobbling together gigs who knows not of office dress codes. The clothes feel overworked, rather than demanding something of the people taking in this formidable creature who should want to wear Do’s clothes.

Fashion industry types have been whispering for a few seasons now that the true spirit of Helmut Lang — weird, sexy, simplistic workwear — is found at Eckhaus Latta, the New York- and L.A.-based label by Mike Eckhaus and Zoe Latta. They were originators of the idea of dressing a New York community, rather than some fantasy person, which is what even European luxury brands talk about today. But their circle has grown way beyond the ceramicists-who-went-to-Bard set. Kelly Bensimon, formerly of “The Real Housewives of New York City,” was in the front row, along with SNL cast member Sarah Sherman and the Dare, a musician who looks and sounds as if Jim Morrison was rejected from the Strokes and wants Julian Casablancas to die regretting it.

Eckhaus Latta started as a brand for the kind of person who moves to a city in pursuit of a creative life and finds it a struggle. Its gauzy cocktail dresses, oxblood quilted trousers, chunky knits and fancy shearlings are more polished, more finished. That earnest vibe feels mature now; the designers are leveling up, growing up.

Maybe that’s the real secret to cool right now: aging. “I love being old!” a millennial Vogue editor gushed to me before Latta and Eckhaus’s show. Now, the designers (who founded the line in 2011) are in their mid-30s, and are survivors instead of strivers. Experience and the tiniest touch of world-weariness can cultivate the looseness cool requires. Perhaps Latta and Eckhaus are showing us how to exit the cringe and embrace middle age.