Leave it to Moncler to make rainy days more enjoyable. Remo Ruffini and his team have designed a pair of pull-on, patent-leather Chelsea boots with a transparent lug sole that maintains traction on slick streets while keeping your feet blissfully unaware of the conditions. And the look is so stylish that we’ll happily wear them on fair-weather days as well—the ultimate compliment for rain boots. ($625, net-a-porter.com)

Languishing through a very gray New York winter, we refuse to let our complexions show any signs of the sunless season. This cream blush from Kjaer Weis, one of the few beauty lines that are truly certified organic, adds a bit of natural-looking flush to both lips and eyes, and the beautiful, refillable packaging encourages even the most low-maintenance among us to re-apply as often as possible. ($56, net-a-porter.com)

There’s no more cost-effective way to freshen up a tried-and-true blazer than with an artful assemblage of pins. Our most recent favorites come courtesy of Don Carney and John Ross, founders of the design studio and store Patch NYC, which is somewhat confusingly based in Boston. These mother-of-pearl beauties are decorated with vintage-inspired images and are thoughtfully endowed with a small loop on the back so that they can be worn as necklaces as well. We generally embrace a conservative approach to layered jewelry, but in this particular case, the more, the merrier. ($36 each, patchnyc.com)

John Derian’s newish Christopher Street outpost is located just a few steps from Air Mail HQ, which means that even something as innocuous as a lunch run to Citarella can be fiscally dangerous for our staffers. Our most recent purchase: this marvel from Derian’s new silk-scarf collection, featuring images from the 18th and 19th centuries that were culled from John Derian Picture Book. ($175, johnderian.com)

Our Barbour jacket does perfectly fine on misty days, but a full downpour requires something stronger. To protect us from the weather gods, Thom Browne’s cheerful yellow trench—made of top-notch glossed polyurethane, trimmed with the designer’s signature stripes, and finished with anchor-embossed buttons—is basically a stylish and wearable tarp: it’s fully waterproof, and skims the calves and wrists for extra coverage. Loosely cut, the jacket has enough room for you to layer away underneath until the temperature transitions from winter chills to spring balminess. Finish with an elegant umbrella from Anderson & Sheppard for bonus points. ($2,700; net-a-porter.com)