My niece Clara came into town last month wearing a pair of penny loafers she’d found downtown in the men’s department in a size 8 men’s, “which is weirdly better fitting than anything I can find trying to wear women’s shoe sizes.” She wanted to know if she looked stupid wearing them.
I told her the truth, which was that she looked better than most of the men I sold loafers to over the course of thirty years, many of whom purchased the correct shoe and then threw it away by wearing it with the wrong everything else.
That’s the thing no one likes talking about when this question comes up. It’s never really about whether women can wear men’s loafers. They can. Obviously they can. Shoes aren’t gender exclusive. They’re designed and built that way.
The actual question, the one worth discussing, is whether the shoe works with your body, the proportions and fit. And that has nothing to do with men’s vs women’s.
The sizing issue isn’t bogus, it just isn’t the issue people think it is
For years I thought the primary issue with women wearing men’s loafers was aesthetic. Some stupid idea that no matter how well they fit the shoe still “looked masculine” and therefore would be distractingly wrong no matter what. That was stupid of me, but it took seeing my own sister in law rock a pair of loafers to understand why. Because it wasn’t the aesthetic at all that was the issue, she just got the fit right.
She wears a men’s size 7, which converts to approximately a women’s size 8 and a half. The men’s size seven has a slightly straighter last, less taper at the toe, a fuller forefoot. Whereas the women’s size seven foot is artificially narrowed, often with a pronounced cone shape at the toe box. On her that blank last, the lack of molding around the toes and balls of her feet, actually makes the shoe fit better than most women’s shoes do in that size range.
The sizing difference itself is negligible, women’s to men’s is about minus a size and a half on average though it scales poorly between brands. Enough that rather than consulting a chart when trying something on yourself, your better off ignoring it entirely. Charts are weird, some brands genuinely believe a women’s size 9 is equal to a men’s size 7 while other brands will say that same women’s 9 is a men’s size 7 and a half shoe depending on which product page you’re reading on their site. TRUST NO ONE THAT SIGNS OFF ON A CHART LIKE THAT.
All that matters far more than what size you wear is the shape of the last and how it looks compared to your leg. That bootsicle of a women’s shoe worn by someone with a thin ankle is going to stick out like a sore thumb no matter how you slice it, just like I stuck out when I borrowed my father’s blazer to fill out for a funeral around a decade I won’t mention. You don’t fix that problem by looking in a different gendered section. You fix it by finding the right width or(last!) the right shaped last for your foot within that gender. Something far fewer people will ask about because they were misinformed about the importance of the larger men’s vs women’s debate in the first place.
The style argument is as old as borrowed closet space
Believe it or not, when I see influencers act like this is a new frontier, some groundbreaking update to normcore dressing, I will bite my tongue past the point of bruising just to avoid saying aloud “I knew women would start wearing mens loafers AGAIN the second it came back as a nineties revival” which is less about the shoe and more about how many cycles of menswear I’ve watched come and go to even consider that.
Women wearing men’s loafers is nothing new, not even remotely. I sold loafers to women regularly for years without anyone ever considering it a statement. Because, again, shoes fit feet. Feet are not conscious of what’s politically correct anymore than your shoes are.
What has changed, and honestly I will admit this part because it’s true, is how they’re styling them now. My sister in law pairs hers with wide leg trousers cut to show the ankle with no socks and suddenly the whole thing looks sharp in a way far too many of my male customers’ outfit built around loafers never quite were. Because we were all taught to match belts and shoes so perfectly back in the day, and considered that finale.
She pairs them with a slip dress in summer, which is one I never would have dreamed of back when I sold shoes but it works. Works enough that the loafers become a focal point rather than some rote afterthought like a flip flop or sandals would. There’s a design reason loafers still exist past July, reasons that pairings like she comes up with drive home whenever someone takes the time to notice.
I want to confront that dick teenager I was who somehow got it into his head that loafers were only acceptable if worn with blunt cuts of pant, wool, preferably pleated, cuffs on those pants, don’t @ me about the cuffs, black leather belt, black leather shoes. Don’t stop there, white button up, no pocket, turn it and blast it. That dumb fuck would look at Clara’s outfit, those loafers with her ankle grazing jeans and boyfriend style button up and assume the entire thing needed to be balanced with everything matching from sock color to purse shade.
It doesn’t need balancing, there isn’t even anything mismatched.
It’s just proportion with far less concern for mundane details then we were taught to worry about. Hell it would have taken that kid, until he hit his late twenties at the earliest, about ten years just to get untrained enough on his own to come anywhere near how Clara dresses now. Same as it took menswear’s obsession with pleated khakis twenty years to cycle back around and still land completely wrong when they did.
So yes, women can wear men’s loafers. Can they look good doing it? Of course, no reason they fucking shouldn’t. The real question is do they know their feet well enough to find a last that fits? Do they care enough about how their clothes look together to build an outfit around a shoe instead of a shoe around the outdated stereotypes of who should be wearing what started this entire conversation?
Clara’s shoes looked great when she asked me about them last month. They look even better now she’s stopped worrying about stereotypes and started caring about fit.
FYI CLARA I WILL NEVER LET YOU LIVE THAT SENTENCE DOWN
Reg spent thirty years buying for a menswear shop floor in Sheffield before it closed. He writes about clothes built to last, compares every new buy with something he’s owned for twenty years, and has made most of the expensive mistakes already.
