There’s something about an elegant black evening jacket or coat styled in a pared-down, modern way that scratches my brain in all the right places. It’s classic and sophisticated, with old-world charm—but, with great denim and left partially unbuttoned for a peek of skin, it gives me the sort-of subversive, high-low contrast I’m always craving in an outfit.

Giorgio Armani, YSL, and Ralph Lauren circa the 1990s; Dior, Chanel, and present-day Khaite; Róhe, Colleen Allen, Laganini Studio, and Liberowe—these are a few brands that come to mind when I think of beautifully-tailored evening jackets. I’ve also had a lot of luck on the secondhand market finding gems from the Victorian, Edwardian, and Art Deco eras. Bonus points are given for a Mandarin collar and ornate buttons, particularly frog closures, tassels, or other types of understated embroidery.

Ahead, a few examples of how I bring this retro staple into modern day. Scroll to the end to shop the best black evening jackets on the market now.

I’ll wear a vintage opera coat from the 1940s with a pair of sock boots and a Gigi Burris hat. This old Celine clasp bag by Phoebe Philo, in my humble opinion, is one of the chicest bags ever made.

I styled this beautiful Róhe jacket with frog buttons with a black tapered trouser. The jacket has a more relaxed silhouette, so these bottoms felt right in their proportions. I topped it off with a Maison Krasnova pillbox hat and vintage pin; Khaite pumps, a tassel belt, and a vintage box bag.

I took an even more casual approach with this vintage puff-sleeve jacket by pairing it with straight-leg, rigid jeans and a great slingback. I pulled it out for another spin on the occasion of a late-fall lunch, styling it with dark-wash denim, a ruffled-collar blouse, and Chanel slingbacks.

I scored this vintage Armani jacket off The RealReal for $80, and I’m obsessed with its structured shoulders. Honestly, Giorgio Armani made the most beautiful evening jackets and blazers, and you can find such good ones on the secondhand market. To make it feel a bit more casual, I paired it with Reformation jeans, a mini Gucci Diana, and Jimmy Choo slingbacks, which I felt complimented the buttons.

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