When looking for outfit inspiration this year, two names always come to mind: Olivia Rodrigo and Selena Gomez. The singers each have their unique style, but in addition to excellent voices, they also have superb taste in fashion. So, when we spotted both wearing a pair of black high-heeled Mary Janes in the same week, you can bet it caught our attention. 

Mary Janes have been around since the 1900s, and it’s safe to say they’ve evolved quite a bit over the past century. Today, stiletto or stacked heel styles can be found just as often as the original flat version of the shoe. From affordable $50 pairs to pricier designer takes on the trend, there’s a Mary Jane out there to suit just about any outfit. 

But, let’s keep it simple: taking a cue from Gomez and Rodrigo, we’ve pulled 14 of the prettiest black high-heeled Mary Janes available to shop now. Suede, satin, and patent leather prevail, with heels coming in a variety of heights and shapes. Not all Mary Janes look the same—and that’s a good thing—so keep scrolling to find the pair that speaks to you, and get ready to strap ’em on for the holidays. 

On Olivia Rodrigo: Shushu Tong dress; Jennifer Behr headband; Christian Louboutin shoes

Rodrigo has worn similar platform pumps on several occasions.

On Selena Gomez: The Frankie Shop coat; Miu Miu jacket and skirt; Khaite belt; Stuart Weitzman shoes

Perfection, no notes. 

Reformation’s stretchy elastic strap is genius. 

Add a few inches (4 and 3/4″ to be precise) with these platform pumps. 

A wedge heel like this is easy to walk in all day.

Not the highest heel, but Larroude’s Blairs are known to be super comfortable. 

A rounded two and double-buckle gives this pair a fun, retro feel. 

A stiletto and super pointy toe makes these Mary-Janes stand out.

How pretty is this buckle?

Satin fabric, a stiletto heel, and a pretty pave buckle makes these Mary-Janes the ideal party shoe. 

Another shorter heel that is too sweet not to include on this list. 

The more you wear these Mary-Janes, the more comfortable they’ll become. 

Whether you prefer a simple buckle or like a stylish T-strap, you really can’t go wrong with heeled Mary Janes this year.