The Perfect Black Loafer For Date Night

For years I was deeply invested in the idea that loafers were a “sensible shoe” thing. You know, when faced with poor desk-job shoe options you grab a pair in black and throw yourself miserably into your work trip. I couldn’t have been more wrong. Allow me to correct myself: when worn correctly, the black loafer is one of sexiest, understated things you can put on your feet for a date. I’m sorry to loafers for mocking them for ten years.

The differences between something chic and something trying too hard lie in subtle details you notice on an unconscious level.

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That slightly chunkier sole to feel modern, not mat schoolteacher. High quality leather that reflects light rather than being flat and matte. Toe shape is important too, too blunt and boxy and it can look clumsy, too sharp and pointy and you just look like it’s 2013.
It all needs a hint of shine, but not too much that it looks lacquered. That’s basically the rubric for everything you own.

So you’ve nailed the shoe itself, how do you wear it? Well this is where the classic black loafer topsoppers of denim-cut slides or things with heels. Once you commit to loafers it’s bare ankle all year round. Rain or shine, if you’re wearing socks with these bad boys you’ve already lost. Pair them with a tailored trouser with a nice sharp crease that hits at the perfect angle to give your legs a break. Or roll up a shirt and slip into a skirt that falls just below the knee, giving you some bare leg to play with before the shoe takes over. Throw it on with a silky button up, half tucked, and you’re looking instantly put together without trying too hard.

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Pop together in five minutes but screams “I made an effort”, that’s the mood you want to exude on a first or second date.

Speaking of first and second dates, let me tell you about the types of nights the loafer is perfect for. Forget weddings, birthdays, or casual jogs in the park. The shoe perfectly embodies situations with undefined dress codes. It’s not quite a “dressy” dinner date, but something more than just a jeans and basketball shirt casual. Something in between; that nice dinner where you hope you’re going to stay for three drinks but also need to be able to walk home without crying. It’s your shoe for the person who matters but you won’t swear that out loud. It’s comfortable enough that you won’t be preoccupied by constant pressure points, sharp enough that no one will think you didn’t try and dark enough to go with whatever sad desk-job attire you decided to change into five minutes before leaving your apartment.