I first wore real loafers for a wedding in 2019. They were penny loafers, brown. Like a sensible pair of brown shoes someone’s father probably bought them to force them to wear. My brother in law didn’t think sneakers would cut it at his reception and he was probably right. Wore them for four hours that day and absolutely hated them. Felt like driving a stick with no clutch.
My foot was sliding around in them every time I made a turn on the dance floor. Threw them in a box in my garage when I got back and didn’t touch them for another two years. That’s my history with loafers, genuinely. Shoes you own but were roped into buying by someone else.
So when I say I’ve changed my mind on loafers let that sit up top because I feel like half the “are loafers back” discourse online skips past these guys. Guys who tried loafers once got the fit wrong, didn’t like how they felt and wrote off an entire category of shoes. That’s on shoe companies selling poorly constructed shoes, not loafers. That’s a guy buying the wrong loafer problem and I think we can agree that’s a completely different question.
My actual take on where things are going, vs what the headlines say
Loafers aren’t here to have a moment. Moments end. Loafers aren’t trending, they’ve been quietly sitting at second in a lot of guys shoe rotations behind whatever they wear around the house/courts five days a week and I don’t think they’re going anywhere. Why? The shift is permanent because it isn’t being driven by influencers and TikToks. Guys are bored of being asked to wear sneakers or shit that covers ankles every time they leave the house. Loafers offered the in between nobody had talked about.
I don’t believe loafers are experiencing some golden age of formality, not anymore. They’re the exact opposite. Loafers are working because they’re the least formal shoe you can wear that still looks like you made an effort. Literally nothing to tie/shoe at six AM. No breaking in period that will have you limping around for weeks before they feel decent. Best of all, no unwritten rule you have to wear a blazer with them to justify pulling them out of your rotation. I wear mine with jeans more than anything. Nobody bats an eye. Guys did that five years ago and got some micro commentary on it to at least try and change your mind.
The whole thing I take issue with when dudes make this like some cut and dry trend story is assuming any pair of loafers will suffice. Loathe me for agreeing with checklists on this but that’s just it. If you try on a cheap pair of loafers with a wooden sole and zero room at the vamp they’re going to feel like shit, just like mine did that day at the wedding. You’ll come away thinking loafers don’t work instead of holding the individual pair accountable. I did that with my first pair. Judged the whole style on one awful evening when I should have been asking if the shoe was built to move with my foot at all. Loafs gotta flex where your foot naturally wants to bend. If they don’t, you’ll feel it within the first six steps out your door.
If they’re actually worth the $$$, tested with only what I trust:
I am not one of these guys who can try a shoe on, face forward in a mirror, and know if it fits just right. So when I actually committed to buying myself a real pair I did what I always do with products. Throw them into the worst conditions possible and see if they survive. Loafers coached a football practice. Wore them to coach a walkthrough practice in October. No pads. Guys are just standing around, pivoting, jogging out to the yard to reset cones, watching me explain a drill for the hundredth time while I ran through my coaching points. Four hours of that on turf mixed with gravel.
I was ready to tear them off at the second hour. That’s how I treat anything that looks good in a box but feels like ass the second I start moving around in them. But these things… stayed. They flexed. My foot slid around absolutely zero. Developed a little sore on the gravel corner of the practice field I’ll be honest I’m still mad about, but otherwise? No rubbing. No heel slip. Not rolling or creasing at the toe wrong. One of my assistant coaches even asked where I got them between drills. Doesn’t get more real of a review than that from a guy more concerned about teaching his kids a new drill than the shoes on his feet.
That right there told me more about these shoes being worth their price than anything else. A $180 loafer that can survive being worked on rough turf and gravel is more valuable to me than a $300 pair that’s literally only constructed to withstand standing in front of a mirror. I’ve fallen for that before. Traded in quality of build for a brand name and wound up with a pair of shoes that looked amazing for the first week they were owned but fell apart at the seams by wear eight. And I thought I was investing in that pair. I wasn’t.
I actually invested when I shoved them on turf no one else was allowed to step on and made them earn the right to take up closet space. Tried them hard and they exceeded my expectations.
That’s how you know if they’re worth your money. Buy a pair. Wear them somewhere that isn’t comfortably inside your home. Let them move around with your feet. If they can handle that you’ll have a good pair of loafers. If they don’t. Well. Box in the garage for you too.
Connor coaches rugby in Bristol and has never quite stopped training. He writes about kit that copes with a proper session and still looks fine on a Saturday, and he won’t recommend anything he hasn’t sweated in first.
