How to Style Cropped Pants for Fall and Winter: A Guide

As someone who denounced cropped pants exactly one year ago, it is with a traitorous heart that I proclaim myself back on the bandwagon. My hiatus has been confirmed temporary.

If you remain taken with long hems, you're in good company; they're still elbowing their way into the popular consciousness via runways and influencers and will likely cement their coup this winter. But I don't intend to be a part of it-at least not religiously. And that's not because I'm anti-puddle hems, necessarily; I've just realized through trial and error that they don't align with my style (crisp, boyish, neat), which is only getting increasingly nitpicky and specific, to my relief. I think the fatigue I felt for cropped pants last fall had less to do with the length and more to do with how unimaginative all the styling was beginning to feel. The near-ubiquitous vintage Levi's. The capris moonlighting as cropped skinnies. The wide-legs verging on culottes. (All perfectly fine if they still give you a good feeling.)

The crops I want today feel distinct. The pants aren't short because some tired designer heard that's what's in; they're short because they're tidy, tailored, and so comfort-oriented they wouldn't dream of bothering you by sweeping along the rat playground known as the New York City subway platform. They're also a little oversized (comfort again) and they're best paired with something like a blazer or a tailored coat to underline the tone of boy-who's-grown-slightly-out-of-his-church clothes. Something like this:

Or maybe this:

And even this (although this crop is a little too generous for my taste):

Also:

And perhaps most importantly:

This last look adds a streetwear twist that feels right. The addition of the hat and the sneakers and the bag around the neck (which I would like to own), remind me of the old men I see running errands in downtown Manhattan. The kind that seem to telegraph "I'm all business both in the sense that I'm wearing a blazer and that I've walked several miles today."

I've become increasingly drawn to style that feels overtly utilitarian like that; so concerned with usefulness that it becomes almost subversive in the process. It reminds me of my good friend Danny, who works as a carpenter and always shows up to things wearing his dirty work clothes and somehow looks cooler than all of us. I don't want to copy his look specifically, but there's something appealing about the fact that everything he's wearing was chosen for its ability to let him do his job. (I once brought him to a fashion show in his work clothes and everyone thought he was a famous artist.) (Maybe he's just one of those people.)

Anyway, I was recently considering why, after all the work we've done at Man Repeller to normalize "putting in effort" when it comes to getting dressed, I still want to look some measure of effortless. And I think it has something to do with wanting my style to reflect my focus. I would prefer my clothes say "I am neat and cherish good design but am otherwise focused on my work" rather than "I almost cried trying to put this together and my room is now in shambles." And right now that feels like sightly (but not too) cropped pants, a nice neutral sock, and well-made pieces that will take me all over New York without feeling out of step or out of place.

What aesthetic do you have your eye on this fall?