Q & Answer: How Do You Pick the Right Shoe Size Online?

Zack writes to us to ask: I’m interested in buying a pair of shoes online, but am having trouble figuring out if they’d fit. I emailed the manufacturer and they gave me the length and width measurements in millimeters. The problem is, I don’t know whether the longest part of my foot aligns with the longest part of the shoe. Do you have any suggestions for what measurements I should ask for, so I can make an educated guess?

I’m not a big fan of measurements for shoes. Like you, I never know what I’m supposed to do with them. 

The length of a shoe can vary depending on a few factors.

  • Size, most obviously. But you’d be surprised how little changes from size to size. The difference can be as small as an eighth of an inch.
  • Welting technique. By welting technique, I mean how the sole was attached to the uppers. The length of your shoes — as measured from the bottom of your soles — can vary depending on the welting technique, as well as within the same kind of construction. Check out the two shoes above, for example. One is from Allen Edmonds, the other from Edward Green. Both are made with Goodyear welts, but the heel on the Allen Edmonds sticks out a bit more from the heel cup, while the heel of the Edward Greens hugs the shoe. 
  • Heel design. Although not as common, some shoes will have what’s known as a canted or Cuban heel, such as these from Saint Crispin’s. Again, compare them to the straight-down heel of the Allen Edmonds shoe above, and you can see how this would affect the measurement of the shoes at the bottom of the sole. 
  • Most importantly, the last. The last is the wooden form on which the leather is pulled over so that it can take a certain shape. You can have lasts in all sorts of shapes. Some shoes can be round and stubby (like Alden); some can be very long and pointy (like Gaziano & Girling). This will affect the length of a shoe more than anything else. You can have two perfectly fitting shoes, but one might be slightly longer simply because the toes were designed to look sleeker. 

In the end, it’s not even the length of your shoes that matter, but rather the heel-to-ball measurement. Critical to your fit is where the heel and ball of your feet sit in your shoes, not whether the ends of your shoe come within a certain distance to your toes.

There’s really only one way to figure out your size online, assuming you can’t try stuff on first.

  • Figure out your Brannock size. Go to a place like Nordstrom and ask someone to measure you. It’s sometimes good to get both feet measured, as few people have the same sized feet. 
  • Ask the store or manufacturer for advice. Not all salespeople will know what they’re talking about, so take their advice with a grain of salt. That said, there are few better places to get sizing advice than from the store or manufacturer you’re buying from. They’re the ones who are likely to be most knowledgeable. Tell them your Brannock size, and if you have other high-end shoes, your size in other brands and models. I don’t mean sneakers like Nike, but rather dress shoes from companies such as Allen Edmonds, Alden, Crockett & Jones, etc. 
  • Check this advice against the forum threads. Styleforum has the biggest archive of all clothing forums, but depending on what kind of shoes you’re buying, Superfuture and Ask Andy About Clothes can be useful as well. Iron Heart and Denimbro are also good for workwear type stuff. The key here is to search the archives before posting anything, as there’s usually a wealth of information you can mine. 

Finally, once you get your shoes, you can check to see if they fit according to this post.

Long story short: measurements are good for clothes, but bad for shoes. To find your size, you have to do some other stuff.

(Photos via Leffot, The Shoe Buff, and Bengal Stripe)

Chelsea Boots
For as long as I’ve been interested in shoes, I’ve always favored boots, and one of the first kinds of boots I fell in love with were Chelseas. Chelseas are a kind of ankle-length, pull-on boot with elastic side gussets. They were invented in the mid-19th century as an alternative to the button boot, but they didn’t really gain popularity until the 1960s, when they were picked up by young men in Chelsea, London (hence the name) and then famously worn by The Beatles (though technically speaking, the Beatles wore a modified version of the Chelsea).
Various English shoe companies make Chelseas in their most classic form (the kind that we associate with the Mod movement of the 1960s). On the uppermost end, there’s Edward Green’s Newmarket, which are fantastically beautiful, but also fantastically expensive. A bit more affordable (but still quite expensive) is Crockett & Jones. They have three versions, simply named models 3, 5, and 8. Their Chelsea 3, being the sleekest and featuring a single-layer leather sole, is the dressiest. Models 5 and 8, on the other hand, are built on studded Dainite soles, with number 8 being a nice, almond-toe compromise between the sleekness of number 3 and the roundness of 5. You can buy these from Crockett & Jones or Barneys New York, though Pediwear, Robert Old, and P. Lal will likely have better prices (note, P. Lal’s prices are denoted in Malaysian ringgit, so you have to convert them).
Slightly more affordable options can be had through Grenson, Shipton & Heneage, and Carmina. Our friends at The Armoury stock the Carmina version in the very sleek Simpson last, while Skoaktiebolaget sells them in the slightly less tapered Rain (a last, as many readers know, is the form that the shoe’s leather is pulled over, and is what determines the shoe’s shape). Carmina can also custom make Chelseas for you, where you choose the last and material, but this comes at a 50% upcharge.
For something more affordable still, there’s Loake and Herring, Charles Tyrwhitt (don’t be fooled by the sale, as they’re always on sale), Markowski, and RM Williams. You can also check eBay, although you’ll want to be careful to avoid the frumpy versions (I’m not a fan of Blundstones, though my friend Jake over at Wax Wane likes them).
If you’re considering getting a pair, try them in black. Those are arguably the easiest and most versatile to wear. If shaped right, and built on a leather sole, they could span everything from suits to jeans. Brown leather would also work well, although on the suit end, they might need to be paired with more casual options (Mark over at The Armoury can be seen here looking great in his tan suit, blue gingham shirt, and Gaziano & Girling Chelseas). Brown suede could also be nice, especially under a pair of tan cavalry twill trousers or some light, washed blue jeans. Whatever you choose, I recommend wearing them with a slim trouser leg, just to keep with the Mod tradition.

Chelsea Boots

For as long as I’ve been interested in shoes, I’ve always favored boots, and one of the first kinds of boots I fell in love with were Chelseas. Chelseas are a kind of ankle-length, pull-on boot with elastic side gussets. They were invented in the mid-19th century as an alternative to the button boot, but they didn’t really gain popularity until the 1960s, when they were picked up by young men in Chelsea, London (hence the name) and then famously worn by The Beatles (though technically speaking, the Beatles wore a modified version of the Chelsea).

Various English shoe companies make Chelseas in their most classic form (the kind that we associate with the Mod movement of the 1960s). On the uppermost end, there’s Edward Green’s Newmarket, which are fantastically beautiful, but also fantastically expensive. A bit more affordable (but still quite expensive) is Crockett & Jones. They have three versions, simply named models 3, 5, and 8. Their Chelsea 3, being the sleekest and featuring a single-layer leather sole, is the dressiest. Models 5 and 8, on the other hand, are built on studded Dainite soles, with number 8 being a nice, almond-toe compromise between the sleekness of number 3 and the roundness of 5. You can buy these from Crockett & Jones or Barneys New York, though Pediwear, Robert Old, and P. Lal will likely have better prices (note, P. Lal’s prices are denoted in Malaysian ringgit, so you have to convert them).

Slightly more affordable options can be had through Grenson, Shipton & Heneage, and Carmina. Our friends at The Armoury stock the Carmina version in the very sleek Simpson last, while Skoaktiebolaget sells them in the slightly less tapered Rain (a last, as many readers know, is the form that the shoe’s leather is pulled over, and is what determines the shoe’s shape). Carmina can also custom make Chelseas for you, where you choose the last and material, but this comes at a 50% upcharge.

For something more affordable still, there’s Loake and Herring, Charles Tyrwhitt (don’t be fooled by the sale, as they’re always on sale), Markowski, and RM Williams. You can also check eBay, although you’ll want to be careful to avoid the frumpy versions (I’m not a fan of Blundstones, though my friend Jake over at Wax Wane likes them).

If you’re considering getting a pair, try them in black. Those are arguably the easiest and most versatile to wear. If shaped right, and built on a leather sole, they could span everything from suits to jeans. Brown leather would also work well, although on the suit end, they might need to be paired with more casual options (Mark over at The Armoury can be seen here looking great in his tan suit, blue gingham shirt, and Gaziano & Girling Chelseas). Brown suede could also be nice, especially under a pair of tan cavalry twill trousers or some light, washed blue jeans. Whatever you choose, I recommend wearing them with a slim trouser leg, just to keep with the Mod tradition.