I spent many years convinced that loafers were NOT a date night shoe. When. You know, those date nights when you know you’re going to hate yourself because your desk-job shoe-game is nonexistent and you just grab a pair of black ones and call it a night? WRONG. Let me rephrase that. When done right, the black loafer is one of the sexiest, most effortlessly chic things you can wear on your feet for date night. I apologize to every loafer I insulted for the past decade.

There’s just something about subtle details that make or break something as chic or desperate to seem trendy. A slightly thicker sole so they feel current, not like you’re trying to teach school again. The leather has to be top tier and actually reflect some light rather than being flat and matte. They need to have just the right amount of shine, but not so much that it looks like they’ve been lacquered. Shape of the toe also matters- too boxy and it can look bulky, but too skinny and pointy and yeah, that’ get you digging through your dad jeans for some distressed tennis shoes. It’s all about finding that in between.

Once you know how to pick out the proper shoe, how do you actually wear them? Glad you asked. Firstly, loafers kid you not about socks. Once you start wearing loafers you will be living bare ankle 365. If it’’re fighting a losing battle. Team loafer means Team Skinny jeans. Match them with a pair of slim fit trousers that have a nice sharp crease and that split just at the perfect angle to allow some cute leg to show. Or cuff up a nice shirt and wear them with a skirt that hits just above the knee to allow for some bare skin before the loafer takes over. Throw a silky button up on with the sleeves half tucked and bam, you look ten times better than you actually tried. It’ll take you five minutes to throw together but will send the message “Yes, I made an effort for you.” That’s what you want to portray when going on a first or second date.
Side note on first and second dates: let me educate you on what the loafer is perfect for. Weddings?

Please. birthdays? Only if they’re your baby mac’kins. Picnics in the park? No way! But if there’ ever been a shoe that was made for ambiguous dress codes, it’ rocking loafers. Sure, it’ not quite dress pants and a button up kind of night, but you know it’ something cute. Maybe a nice dinner where you hope you get to stay for 3 drinks but still need to be able to walk home. They’ comfortable enough that you won’t feel them but won’t cause you to hobble home from rubbing your heels raw, classy enough that no one will think you didn’t dress up but dark enough that you can pair them with that necklace your mom got you to go with whatever sad desk-job clothes you threw together in the five minutes before you left your apartment.

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