To be crystal clear: we are all for wearing boots with your finest tailoring. It’s a menswear micro-swerve we fully endorse—when it’s done right. But like other shoes, the boots you wear have to work with your suit and not against it. Unfortunately, at last night’s BMI Country Music Awards the boots Keith Urban chose, torpedoed his perfectly stylish gray plaid suit. If his suit said “I’m a slick rock ‘n’ roll type” his boots were saying they had a shift at the plant to punch in for. This look would have been a home run if there were Chelsea boots beneath those pant hems. Or glossy black combat boots. Or oxblood dress boot wing tips. Really anything but these gray suede hiking-inspired things.
Finding the right pair of boots to wear with your suit is like finding a perfect match on a dating app (except the shoes don’t have to like you back). And when it comes to Urban’s lug-sole lace up boots, the singer should have swiped left. They’re not the worst boots in the world, they just aren’t a good match for this suit. Look at all the wrinkles and puckering in his pants, that’s what happens when your boots are chunky and your suit pants are slim. The correct boots will allow your suit pants to fall over them without getting stuck.
Your first priority when attempting a boot-suit match should be proportion. It’s important to try your suit on with a few different pairs of boots before you walk out the door. And if you don’t trust your own visual acuity ask a friend or your significant other to help—where was Nicole Kidman yesterday? And don’t forget to consider the color of your boots. We spend a lot of time talking about the benefits of tonal dressing. And it’s true the monochrome style tactic is very useful when you’re bored of basic suit pairings. But Urban’s boots are proof that colors that match too perfectly drown their wearer rather than making him look good. In general you want to find a pair of boots in a color one or two shades away from your suit. Same goes for the shirt or slouchy goth henley you choose to wear. For the record the color of Urban’s shirt is the right amount of tonal distance from his suit. We’ll save his sleeves situation for another conversation.