Olatz Schnabel could only take so much. After years of attending cocktail parties alongside her then husband, the perennially pajama-clad artist Julian Schnabel, she decided to make some sleepwear of her own. Made-to-order in 100 percent silk, perfectly piped and conveniently unisex, they are offered in more than a dozen colors. While we tend to leave our loungewear at home, the tops of these timeless sets rival most festive silk shirts, the unofficial holiday-party uniform. ($600, olatz.com)

Back in 1995, Giorgio Armani sought to answer the eternal question: Is it possible to carry one bag from day to night? The slim little shoulder bag that ensued was inspired by the shape and sensibility of another equally versatile piece—the Armani tailored jacket. Now the designer has taken inspiration from his 90s classic and introduced a collection of six new bags called La Prima. Our favorite is the smaller version (which holds plenty, thanks to its accordion shape) made of palmellato leather in a lovely shade of azure. The adjustable shoulder strap means that it can be carried crossbody, and inside you’ll find a lipstick case and mirror. Invest now, enjoy forever—just as Mr. Armani intended. ($1,595; armani.com)

If you’ve avoided buying anything from Gen Z favorite the Reformation, we understand. Between the comically short hemlines and absurdly revealing slits, the dresses are merciless. But on occasion they produce a winner, and this season it’s the Mary dress. With a fitted bodice and flowing midi skirt, it pairs beautifully with a trim cardigan or cropped jacket, but it’s perfectly street-safe on its own. The dress’s most obvious virtue is its fabric—a lightweight, soft stretch knit derived from eucalyptus trees in a closed-loop production cycle. (Approximately 99 percent of the nontoxic solvent is re-used.) All of that aside, it’s more comfortable than most of our pajamas. Wear with abandon! ($98, thereformation.com)

If you can’t stomach the sight of another nylon puffer, help is here. You wouldn’t expect anything quotidian from Tom Ford, would you? At a distance, his quilted leather jacket may look like the all-weather basic worn by throngs of New York City straphangers, but a closer inspection reveals that Ford’s version is magnificently constructed from Nappa lambskin. It’s filled with goose down, to ensure warmth, and is remarkably lightweight, and, should conditions permit, the hood is detachable. Best of all, it looks remarkably smart, which, for a puffer jacket, is really saying something. ($8,850; tomford.com)

Perhaps you’re preparing to decamp to the tropics for the season, or maybe you’re staying put in a wintry wonderland. No matter: any decent optometrist will tell you that sunglasses are a year-round essential, which means that it’s probably time to cycle in a new pair. Le Specs does a very cool cat-eye, especially in this olive-green shade. Accented with gold-tone metal bars, and set with UV-blocking brown lenses, they bring an awful lot of style at an inoffensive price. ($48, matchesfashion.com)