It cannot be overstated how important the heel of a shoe or boot is for providing support, stability, and comfort to the person who wears it. Perhaps equally as important is the impression that your heels give off to those around you—if they’re anything but a standard block heel (which of course we detail below!) it’s likely one of the first things people notice about your footwear.

With that in mind, we’ve prepared a rundown of all the essential heel types you need to know about, along with some context on their purposes and where they came from. We’ve also enlisted the help of Jake of Almost Vintage Style to provide his impressions of wearing and styling some of these heels, and to guide us in choosing the right heel design for the right pair.

almost vintage style heels

But first, Jake’s manifesto on heels:

To me, the most important factor to keep in mind with heels is visual balance and proportion. Certain heel shapes tend to look good with certain boot styles and lasts. Part of this is due to convention and what our eyes have become used to seeing, but also because certain shapes and angles look good with each other. 

As a general rule, heels and lasts complement each other best when they have a similar style. A curvy, rounded last tends to look good with a curved heel; a sleeker last tends to work best with a sleeker heel; and a chunky, bulbous last will usually work well with a chunky heel. This of course is not universal, but it is a helpful guide.

Everyone’s tastes are different, and we’re all drawn towards different kinds of heels. Personally, my favorite is the woodsman heel. However, woodsman heels do not actually look good with every boot design and/or last, and the same goes for other heels. There are some cases where multiple kinds of heels and soles would work with a particular boot, but this is not always the case.

With that, let’s dig our heels in…and look at some heels.

almost vintage style block heel

Block Heel

Design: A straight-up-and-down heel, where the edge of the heel stack sits at a 90 degree angle to the ground.

Purpose: With its broad base that eclipses the surface area of the wearer’s natural heel, the block heel provides ample balance and stability for standing and walking around. It’s difficult to say where the original block heel came from, but because of its straightforward design, it seems possible that its lineage may go back to the 10th century, when Persian soldiers found that heeled footwear helped them stay firmly in the stirrups while riding their horses.

Commonly Found On: A wide variety of boots and shoes, both formal and casual. The height of a block heel will vary depending most crucially on the shoe last it is coupled with—many lasts somewhat demand a certain heel height for proper function and comfort. At times customer preference can also come into play, with some makers offering shorter or taller heels within a designated range of last-harmony tolerance.

Jake’s Take: These are not my preference by any means, but that is mostly because they look great with boots that are not my preference. Still, a service boot with a low block heel is a perfect combination and no other heel does that boot equal justice. 

Due to the fact that block heels are…well…blocky, they tend to look better at low to medium heights. If they are too tall, they tend to look rather cumbersome and clumsily designed. As such, they seem to work better with sleeker boots. Dress boots and shoes, derbies, service boots, low monkey boots, and chelsea boots all look fantastic with this heel style, while loggers, engineers, or anything with a sprung toe looks ill-proportioned in my eyes.

almost vintage style logger heel

Logger/Woodsman Heel

Design: A heel with a concave line, tapering inward from the base of the boot itself towards the ground. Traditionally, the logger heel (also known as a woodsman heel) will sit at a height of roughly 1.5 to 2 inches. Shorter logger heels, often known as low woodsman heels, are usually less than 1.5 inches tall.

Purpose: The typical logger heel’s taller height provides the wearer (lumberjacks, originally) a great deal of traction, allowing them to traverse steep, uneven terrain as well as climb up trees (which also became very handy for folks like linemen and arborists).

Commonly Found On: Originally logging boots and various other boots used in forest settings, though today they can also be found on various footwear worn for fashion, such as engineers or service boots.

Jake’s Take: Again, this is by far my favorite heel style. This curvy heel tends to look best at a fairly tall height of at least 1 1/2″ to 2″ tall. To me, the sweet spot is around 1 5/8″. Anything too low throws the proportion off and misshapen. Anything with a really low woodsman heel probably looks better with a block heel. My favorite style of boot, the engineer, looks perfect with this type of heel. Lace-to toe-logger boots also go well with this style, as do packer boots, semi-dress styles, and chunkier monkey boots. 

One thing to keep in mind with these heels is that given the height and smaller surface area, they could take a little time to get used to walking in. You’ll get used to them after a short period of time and they may end up being the most comfortable for you. They certainly are for me. 

Whatever you do, do NOT call this a Cuban heel because it’s definitely not one. (We’ll get to that one later.)


lucchese carson black calf

Cowboy Heel

Design: A heel around 2 inches in height with a slanted heel stack, where the edge of the stack is roughly 120-130 degrees from the ground to the base of the heel, tapering inward. The breast of the heel (the front of the heel that sits under the foot) is often tilted slightly back.

Purpose: This slanted heel is designed for horseback riding. Not only does the heel allow for the rider to keep their feet from slipping out of the stirrups, its less-blocky design can also be gentler on a horse’s midsection.

Commonly Found On: Western boots, specifically cowboy boots.

Jake’s Take: Cowboy heels can vary widely in height and style. I am not all that qualified to discuss the practicalities of these. The last time I was on a horse was over 15 years ago. However, if you are wearing these for style (and if you are reading this article, that’s probably the only reason you would wear them) then I would caution you to not go too crazy tall in the height or narrow in the surface area with these. It can get a bit costume-y. Keep it around the height of a woodsman heel and they can look fantastic, though.

almost vintage style dogger heel

Dogger Heel

Design: Similar to a cowboy heel, though typically with a height of around 1.25 inches. The back of the heel is typically set at an angle, while the sides are more straight. The heel breast may or may not be at an angle as well.

Purpose: This shorter angled heel is ideal for steer wrestlers—otherwise known as bulldoggers, or simply “doggers.” Because of the nature of steer wrestling, it’s beneficial to have a heel that can be used for short bouts of riding while also providing slightly better traction on the ground.

Commonly Found On: Western boots as well as some work boots.

Jake’s Take: These are similar to Cuban and Cowboy heels, but chunkier and with a larger base surface area. I have these on my Nick’s Robert boots and I love them on that pair. Basically, these look great on serious PNW work-style or true work boots. I wouldn’t ever put them on an engineer, but they work on semi-dress style boots quite well. As with woodsman heels, dogger heels may take a little getting used to.


grinders arizona cuban heel

Cuban Heel

Design: Cuban heels are often conflated with dogger heels—some people may even use the names interchangeably—but technically the Cuban is more like a cowboy heel in that the back and the sides of the heel taper inward from top to bottom, while the heel breast is typically straight rather than angled.

Purpose: For non-work boots, these heels provide decent support as well as a bit of flair, and are often used by flamenco and tango dancers.

Commonly Found On: Work boots as well as fashion boots, such as side-zips or chelseas.

Jake’s Take: This is basically the same as some types of cowboy heel, just not on a cowboy boot. These are usually quite severe in their angle and are usually on laceless pull on boots. Specifically, they are usually found on Chelsea boots or other sleek pull on models. Certain cowboy heels can look quite sleek, pointy, and sort of dressy, and the same goes for the Cuban heel. 

This type of heel generally looks best with a sleeker, slimmer boot. Take a look at Beatle boots for inspiration, or YSL boots if you want something more modern. My Benzein Chelsea boots have something that is either a subtle cuban heel or a low dogger heel on it. I can’t really decide which it is, but either way it looks great and really ties the boot together.

Additionally, a lot of sleeker dress shoes have slightly tapered heels, almost akin to a Cuban heel. To be perfectly honest, this style may have a different name, but I do think it looks great on some bespoke dress shoes.

Big thanks again to Jake for helping us out with this story. For more footwear and clothing reviews and ruminations from Jake, check out You can also find him on YouTube and Instagram.


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