A lady came into the store a few months ago waving her phone like she caught someone cheating. There was some article online that said if you wear a women’s 9, you should wear a men’s 7.5. She wanted Timberlands but she wanted the real men’s boot, not the women’s cut with the skinny heel and fourteen shades of brown nobody over the age of twelve wants to pick from. I sized her on the kids mat in the back, because it’s flat and the ruler is built into it, and her foot measured ten and a quarter inches. Men’s 8. Not 7.5.

Close, but close enough that she would have bought the men’s 7.5 and been sliding around in her boot by the second month because it pinched her toes and blamed the boot instead of simple subtraction.
That whole minus 1.5 thing gets thrown around so often it sounds like it’s chiseled into a wall but nobody can find the dang thing, and I get it. It’s easy. Short headline. Quick math. Simple answer. But that formula is created by crunching averages of old lasts from years of shoe production as opposed to your living, breathing foot and it’s the disconnect between the math and your foot where people start buying the wrong size and declare they “just don’t like men’s shoes.”
The Size on the Tag Was Never Really About You
Tldr; men’s and women’s shoes are not the same shoe resized. But let’s dive in:
Men’s shoes and women’s shoes are built on different lasts. The last is the molded foot shape each shoe is built around, and male lasts are traditionally wider across the forefoot, and have a smaller depth through the arch than women’s shoes of the same length. Meaning even if you match up in length you could still run small or large in the width department.
What I mean by that is let’s say your foot measures right on the inch where the size jumps. An 8.5 isn’t always going to fit the same in every brand because brands don’t all resize the same. So it’s always best to compare your foot length to what you’re actually trying to buy.
I’ve had plenty of women’s customers come through who were told that since they wore a size 7 in women’s boots, they would also wear a size 7 in men’s. That’s just false and I don’t care how many Times they’ve done it before.
Same thing goes backwards too. I had a customer last spring who was a sales rep working trade shows. He had been told by 3 different retail stores that a European Size X converts straight across to women’s and men’s. WHICH IS COMPLETELY FALSE for anyone who doesn’t have a foot that sits exactly in line with what each brand identifies as their “standard last.” Close problem, opposite direction, but it’s the same issue of gatekeepers handing out “easy math” when they’ve clearly never used a tape measure on someone’s foot.
The problem is when a company tells you Women’s 9 = Mens 7.5 that’s them saying “Hey on our last, with our average measurements our women’s size 9 foot is roughly the same length as our men’s size 7.5 foot.” Again,roughly. Not your foot. Not the boot you have in your hands. Not accounting for brands that run their mens lines at a half size generous and women’s true to size. Words they don’t want to say out loud because it happens way more than anyone wants to admit.
I’ve measured two pairs from the same company, same year, drastically different styles. Literally watch the insoles pulled out and watched them differ by almost a third of an inch at the same tagged size. That’s not coincidence, that’s a brand refusing to communicate between departments.
What your tape Measure Says vs How the Fit Actually feels
So what I would do, what I actually recommend instead of some arbitrary math is this: Take your time. Get a tape measure and measure your foot. Not while you’re sitting down. Heel to longest toe with weight on your foot like you would actually be standing in the shoe because your foot spreads when weight is applied to it. Then scrap the -1.5 rule from your brain and find that shoe’s actual size chart.
I’m not talking about the one on Amazon or the brand’s own site that just lists numbers. Dig until you find one that lists what it measures down to in inches or centimeters at each size. Because that’s what you just measured yourself as. Match that men’s shoe’s inches to your foot’s inches.
You know what else isn’t a coincidence? Once you’ve found your length, and you pay attention to the shoe’s width you will find that every pair of men’s shoes will fit slightly loose in the midfoot compared to women’s because of that last shape we talked about earlier.
A lot of women new to mens sneakers or boots will get the length correct but have a foot that slides at the heel because men’s shoes have more room to move around front to back as a standard.

We’re not picking shoes to torture women here, that last just naturally fits the average widest point of a mans foot better. And thicker socks or insoles aren’t cheating, our stores just aren’t building women’s shoes with that same extra room in mind because for the longest companies didn’t feel women bought enough sneakers to warrant the expense.
I’ll be honest, there aren’t many brands that get it right across the board where you don’t have to think about what you’re doing. A pair I sold recently actually had half sizes stamped out for their entire men’s line with a width key on the box to boot. No guessing, no weird math needed. Because once you know your foot measurements, and match that to the shoes you ARE buying you’ll be golden.
I think it would be wonderful if that was common instead of the standard, but it’s not. Half sizes, measuring width. Brands dropped the ball decades ago and too few have bothered to pick it back up. You’re not obligated to continue doing business with that mentality.
Terry works a menswear shop floor in Newcastle and is a big and tall specialist himself. He writes about sizing that holds up, measures things before he believes the label, and has strong opinions about the phrase relaxed fit.



