Think of this woven-leather Nantucket basket bag as an elegant cross between a canvas tote and a proper handbag. From Dragon Diffusion, it’s roomy enough to hold sundries and supplies—a very stylish reusable grocery bag—but sufficiently put-together to communicate that you did, in fact, get dressed today (even if you’re destined only for the corner market). The long handles fit comfortably over the shoulder, while the shallow shape ensures that your favorite lipstick won’t be lost. And just imagine how, in sunnier times, it’s just the thing to take to a rocky beach in Ischia … ($327, pre-order on matchesfashion.com)

No offense to our 13-year-old Barbour, but it’s not ideal protection in a downpour, even with its annual wax. Enter Stutterheim, founded in 2010 by erstwhile advertising copywriter Alexander Stutterheim, after he discovered a raincoat of his grandfather’s and reimagined it with some modern flair. (Who can resist a brand whose slogan is “Swedish melancholy at its driest”?) Today, the label sells short styles, long styles, styles for kids, and even rain boots, all crafted with obsessive attention to detail. For women, the Mosebacke is a favorite, thanks to its roomy, A-line silhouette, which lends itself especially well to layering sweaters underneath. We’re partial to the traditional yellow color, but it also comes in navy, black, burgundy, pale pink, light sand, and a fetching shade of Army green. ($295, stutterheim.com)

We’ll have what she’s having. And by “she,” we mean Khaite designer Catherine Holstein, who can do very little wrong (except charge $3,600 for a ruched-twill evening gown with awkward cutouts, but that’s another story and we’re in a forgiving mood). Now she has trotted out her take on Adidas Originals running shoes, Khaite-ified with sand-colored suede uppers and tonal laces. They’re just the thing to walk around both city and country, and will dress down a floaty spring dress in all the right ways. Spring is coming, right? ($230, net-a-porter.com)

Yoshitomo Nara and Stella McCartney have teamed up on a capsule collection that is sure to appeal to art and fashion experts alike. Channeling some of Nara’s favorite themes—revolt, self-expression, and punk—the collaboration, titled Stella Shared, features a range of silhouettes designed with gender inclusivity in mind, and everything from knits to tees and totes to trousers. We’re especially partial to the printed silk blouse, paired with sporty pull-on pants finished with a stripe of McCartney’s reworked logo. (stellamccartney.com)