A pair of shoes can look fantastic and be constructed to impeccable standards that will make them last for years—but if they don’t fit your foot correctly, they’ll end up sitting in a closet, utterly lonely and questioning their purpose in life. That’s an extremely mean thing to do to your shoes.

So how should a piece of quality footwear fit? It’s a tricky question, given the realities of shoemaking: different brands who use lasts of different shapes and a range of sizing grades. And let’s not forget that no two feet are identical.

But the best overall answer may well be: your shoes probably need to fit more snugly than you think.

I spent hours tearing through the big question with Jason Pecarich, owner of Division Road in Seattle, which sells what Jason refers to as “handgrade footwear” from Tricker’s, Viberg, White’s, Wesco, and more.

Division Road also upkeeps one of the most detailed and helpful sizing guides of any retailer, and Jason and crew spend whatever time is necessary going back and forth with in-shop and internet customers alike to ensure they get the right size shoes and boots. All of which made him particularly well-suited for me asking this most impossible of questions.

One thing to remember: This is a general guide that speaks to quality footwear, well…generally. It doesn’t get into things like how loafers should fit vs. oxfords, for example. Or how you should fit into a specific brand or last compared to hot you fit into another brand or last. Although we’ll definitely be doing stories like that as well in the future! It’s just not what this particular story is. Definitely leave a comment below, or send any questions to hello@stitchdown.com or DM me on Instagram at @stitchdown with anything else you’re wondering about.

To the guide!

If You’re Thinking About Your Sneaker Size: Don’t

Many heritage shoemakers have been around for 50 or 100+ years, and have worked off a consistent sizing grade system that entire time. When sneakers became abundant in the 1950s and 60s, the companies creating them skewed that size grading as they attempted to size closer to Brannock device (the big silver metal thing) measurements. But the shoemakers that had been crafting the same shoes (on the same lasts) for decades couldn’t very well go and change their sizing—it would’ve completely thrown off what their dedicated customers were accustomed to.

Which gets us to where we are today: sneaker sizes that are often right at Brannock measurements, or even sometimes a half- to full size above them, while shoes from historic handgrade makers come in often a size, or sometimes up to two sizes, below those measurements. And none of those shoemakers care about your size in Jordans.

Don’t Get Hung Up On a Sizing Number: Think About How the Shoe Feels

Is it unsettling, and weird, and a little oddly demeaning to get sized into a shoe that’s two sizes smaller than what you’ve always considered to be “your” size? Absolutely! But a number is just a number, and you shouldn’t be afraid of it. What matters is how, oh so poetically, the shoe fits.

Shoe Size Conversion—Tricker's UK Size

Which All Means: You Are Almost Definitely Going to Take a Smaller Size Than You’re Used To

And that’s fine! You just need to get used to it. You also need to consider that sneakers and many other forms of less well-built footwear are generally designed to stretch significantly due to being built with synthetic materials, padding, and rubber compounds.

Plus, many of us are used to swimming around in a shoe—we think that’s part of what makes it “comfortable.” In almost all cases when it comes to quality footwear, we are wrong. Getting the right shoe for your feet can have huge benefits—from true comfort to better overall health for your entire body—but for a shoe to offer proper support, you can’t be sliding all over the place while walking around in it.


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Sizing Too Big Can Be Very Bad—Especially Over the Long Term

And especially with bullet-proof, impeccably built shoes, which “can weigh up to two pounds per boot, and if you start off too large and spacious they will end up sloppy and ergonomically unsound,” Jason says. “But that weight is going to be hardly noticeable in the right size, and the boot will mold to your foot to a greater degree when sized properly. In short, you want footwear like this on the tight side.”

Quality Footwear Should Fit More Snugly Than You Think, and Possibly More Snugly Than You’re Ready For

Jason’s rule: “Go down to the smallest your foot can fit into, and then up a half size. That’s probably your best bet.”

And Don’t Be Afraid of Your Toe Being In There More Tightly Than You’re Accustomed To

This is another scare point for a lot of people. “The big rule is you don’t want to be touching the front of the toe box” Jason says. “But outside of that, in the right size you can be really close and almost grazing, to .75 inches away depending on the foot-to-last combination. Dress lasts often have extended toes as not many feet are shaped with a point to them [ed note: hard deadpan there]. Hence, very few will fill the front completely.”

Shoe Sizing Guide—Crockett & Jones

But When Is Snug Too Snug?

“I think the overarching rule is to acknowledge the data,” Jason says. “If you’re getting blisters, pain, lots of movement, slop—that is probably not your size. Uncomfortable is somewhat acceptable at first, but if a person has a high instep and it’s a low volume last/pattern combination, that might not be right for them. It should be evident when during the post break-in period a shoe or boot is causing pain.”

But of course nobody wants to figure it out after they’ve already worn a shoe and can’t return it. Which is why it’s important to 1) deeply consider the rest of this guide. 2) Go to a shop that constantly sizes customers into the shoemaker you’re interested in and therefore really knows their stuff. If that’s not possible 3) call or email them to talk things through. And of course, 4) deeply consider the rest of this guide!

Your Foot Extending Out Over The Edge of the Shoe Isn’t Necessarily A Bad Thing

Which is something you’ve maybe heard, and possibly feared. “This goes into the foot to last combination, and how the upper pattern is designed as well,” Jason says. “But most people in the right size are going to have an area of their foot that extends over the insole. I’m not sure why guys get hung up on that.” I know I have in the past.

Shoe Widths Are Less Important Than You Might Think

This part of our talk was honestly one of the biggest revelations for me. “Just because you have a wide/narrow foot it doesn’t mean a width increment is going to match your foot better,” Jason says. “Really there is almost no difference between a D to E, E to EE, EE to EEE in the same size. If you’re a C to E you’ll likely be fine in average D/E footwear.”

“But an EE width foot does need a last that can accommodate that, and a B width foot is not going to be well suited in an average width last/size either.”

Don’t Get Too Hung Up on U.S. vs. U.K. Sizing, Either

“Everything gets so archaic in the handgrade category, the international sizing between US/UK doesn’t mean a whole lot,” Jason says. “For example, Viberg, Alden, Tricker’s, Crockett & Jones—they’re all about 1.5 sizes down from a common sneaker size. Meaning they are all on the old grading method and 7 Viberg = 7 UK Tricker’s = 7 Alden, generally.” Again: generally. Pull on as many data points as you can—the ones emanating from your actual feet being the most important—to make any decision on a specific pair of shoes.

J. Fitzpatrick Shoes—Shoe Sizing Guide

The Socks You Wear Can Make a Difference—But Not Always

“It’s really not thickness that matters, as a foot will swell and contract more than any sock dimension is going to change size,” Jason says. “When guys start citing ‘I wear these socks with these boots,’ we know they are trying to cheat a size that might not be right for them.”

That being said, not all socks are the same. “Dress socks made of fine merino, cashmere, or mercerized cotton have very little friction and footwear with weight to it is not well suited to a sock like that. The foot will feel more movement—especially versus a ‘boot’ sock that has a lot of texture and friction that will hold the boot against the foot better. If a guy wears almost all no-show or dress socks with shoes, he should size on the very small size to limit slippage.” 

Handgrade Footwear Will Flex and Mold to Your Feet Far More Than Lesser Shoes Will

Which means, since most people’s feet are slightly different sizes, you always want to think about your smaller foot—not your larger one.

“With re-buildable footwear that will mold to your foot, we size to the smaller foot, and the larger will force the shoe open to a greater degree,” Jason says. “You can’t really do this with most common footwear. We suggest fitting a fully rebuildable boot like a Viberg, Tricker’s or Wesco to be as snug out of the box as possible, as this build is using heavy-duty all-natural materials and will give, flex, and mold to your foot with the proper pressure.”

“That grade of footwear flexes rather than ‘stretches,’ which is more typical with cheaper or lighter leathers. Our builds will give about .25 size in the long run, on average. This is more than just the upper, but depending on the build, the leather insole will mold and compress to the foot. Cork/insole filling will also compress. Stitchdown boots you will get more lateral give across the width of the boot, and with welted products you’ll get more volume,” because of how the shoe is constructed, and owing to a slightly deeper footbed well. “We’re talking a millimeter but the foot might feel it differently.”


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It’s Important To Understand What Kind of Last a Shoe Is Built On

“Work boot lasts are designed to accommodate a wide variety of feet, and are generally higher heeled, and designed to take an insole,” Jason says. “Dress lasts are going to have more extended toes—so you don’t worry so much about length—and grip the foot in the toe box through forefoot.”

“Munson or military-based lasts have more rounded toe boxes with generally room for the toes to splay, but should have a lot of taper from the waist into a narrow heel. You have to think about how the shape dictates the last type, and then how that should fit.”

“There is the most confusion when guys go from a work boot or Munson-based last into a dress-styled last. They are used to having their feet free up front, and then go to something that’s the reverse of that fit and feel. They assume the last is too narrow, but aren’t used to having the front of their foot gripped.”

Division Road x Trickers Dean Boot

Always Remember That Different Leathers Have Different Levels of Give Over Time

“Roughouts and suedes will not give as much in terms of ‘stretch’ as that is the reverse of the grain, meaning the hide has been stretched on the animal,” Jason says. “So they don’t open up as much in the long run. They also have more structure than a grain-side leather so they hold their form a little more.”

“Tannage will also have some impact on this, as chrome or oil tans generally have more elasticity, while vegetable tans will give and mold to a greater degree.” A good way to think about this is how much a hide stretches and bounces back (elasticity) vs how much it molds permanently over time. “The hide type does have an impact as well. Horsebutts are shell-like in terms of rigidity and mold more than shell, but don’t flex a ton. Horse is the most durable common leather as the hide is not as stretched on the animal and has a tighter grain structure than steer or calf. They take longer to break-in generally.”

“The highly finished or mulled leathers take a really long time to break-in and don’t flex as much. They just have a lot of material after tanning in them for shine, durability, and more structure. Some of these, like those that Tricker’s uses, are high quality—but some others are just covering up cheaper hides with these methods.”

And There You Have It

Don’t get hung up on “your size” or widths, be unafraid to go snug, know your lasts and leather types and how they’ll evolve as you wear your shoes, and whenever possible, go talk to pros who do this all day long for a living. And in the end, make sure you size yourself into shoes whose fit you’ll enjoy for a long time—which is the entire point.