When it comes to outerwear that will stand up to the cold winds and rains that are, as the poet said, icumen in, it’s tough to beat the original foul-weather gear created by Mackintosh. Started almost 200 years ago by Charles Macintosh, after he invented a way to rubberize cotton and make it water-repellent, the company has created rainwear for the British military, railway workers, and just about any sane person who wants a guarantee of staying dry. The Chryston model is among our favorites, not just for its minimal but vaguely mod cut, but because its hood makes it perfect for all those days you forget your umbrella—or just want to grab a power nap on the train ride home. ($1,675; mackintosh.com)

We love the idea of a shirtdress, but all too often they’re made of shirting fabric—a boxy, wrinkly proposition. (And the bottom button is never properly placed, resulting in occasional indecency, but that’s a story for another day.) The clever designers chez A.P.C. know better, and the French outfitter’s new Rosie style uses a floral-print silk twill that drapes beautifully. A bit beyond knee-length, it has the structure of a very good shirt combined with the ease and style of a day dress. Ideal with sandals for now, but it will work with boots and a cardigan until further notice. ($635, apc-us.com)

In the early aughts, one couldn’t walk down a street in certain Manhattan neighborhoods without encountering a Dior Saddle bag. One of the most remarkable successes in fashion history, it owns a fair amount of its popularity to Sex and the City’s Carrie Bradshaw, who trotted hers around town with abandon. The bag eventually rode into the sunset, but it became A Thing again in 2014, when Beyoncé was spotted carrying a vintage edition. In 2018, Dior creative director Maria Grazia Chiuri relaunched it to great fanfare, and each season they’ve gotten more fanciful. For the minimalists among you, there’s an “ultra matte” black version, but we’re even more charmed by the embroidered calfskin version, which features a Toile de Jouy Tropicalia motif, rendered in thread and beads. ($5,600; dior.com)

Meghan Markle isn’t the only one who relies on the West Village sweat fest known as Modo Yoga—the studio conveniently located mere steps away from air mail HQ, which means that on any given Tuesday you’re likely to see at least one of us there, suffering through crow pose while wearing Carbon38’s Takara leggings. Made of some witchy combination of nylon and Lycra, they’re both flattering and breathable, which is key when you’re nearly naked and suffering in a mirrored room. They also look great on the street, paired with a sporty anorak and an air mail tote bag. Generally, we are loathe to buy anything but skivvies and socks in multiples, but your style correspondent proudly owns six pairs of these. (Black, navy, forest green, burgundy, “denim,” and, next, iron.) ($98, carbon38.com)

If seeing last season’s salt-crusted boots lurking in your closet inspires you to pop a Xanax, well, join the club. No offense to those workhorses, but if we’re going to willingly march into another interminable New York winter, we’d better be doing so in new shoes. Enter Ralph Lauren’s Caia Buttoned Booties, a smart alternative to the stompers you’ll be living in all too soon. Designed to resemble vintage spats, they’re made of calfskin and goat suede, with a 15-mm. heel that provides a bit of lift and a lot of comfort. Finished with a faux pearl and dainty crystal, they’re destined for the very best autumnal walks around town. And when worn with pants or long skirts, they make a very solid option to heels. ($1,200; ralphlauren.com)