Let’s start with a disclaimer: everything I am about to say is totally dependent on your tastes and preferences. There’s no such as the perfect work boot, because every foot, every job, every worksite is different.
Each job has its own demands. If you’re a handyman doing odd jobs in customers’ homes, then a pair of sneakers can be enough. If you do remodeling, a non-marking sole is key, to avoid damaging the existing floors in a client’s home. Roofers should prioritize grip and ankle support. I can’t tell you exactly what boot is right for you, because it’s just not that simple.
What we can do is look at the different variables and give you a good starting point for a variety of types of boots and offer a few of many potential options that might suit you. We’re going to talk about seasonal considerations, toe options and options to improve comfort and fit.


Boots come in a few different ankle heights. Your choice may depend on comfort, support and/or protection against the elements or the job.
Low cut models can be cooler in hot months. They also may be more comfortable if you are often kneeling during the day.
Mid-cuts (up to 6” shaft, measuring from the arch) offer a bit more support in the ankle. If you have a history of ankle issues or are standing much of the day, but also need flexibility in the ankle, these can be great.
High-cut boots (8” shaft or higher) provide ankle support through long days. If you are on your feet all day and do a lot of heavy lifting, these can help your feet survive the day. In the winter they add a little extra warmth and protection against the elements.


There are three options for boot toes: soft toe, steel toe and the newer composite toe.

Soft Toe

A soft toe is only appropriate if you are at no risk of your foot being crushed or pierced. Also make sure that your worksite doesn’t require a safety toe boot. A good example of a comfortable soft toe shoe is the Sears DieHard. Some contractors report that the grip isn’t very good, so I would recommend the SureTrack version, to give yourself a little more traction. These have the 6” rise, but you can also get a higher ankle for more support or an Oxford, if you’re in homes or your shop.

Sears DieHard Boot

Sears DieHard Men’s Boot

If a safety toe is required or just a generally good idea, there are several factors to consider.

Steel Toe

A steel toe is the old classic. As far as straight impact resistance, the steel toe can handle more. If you’re in a highly hazardous environment, steel is the way to go.
Not all steel toes are clunky, old-school boots. KEEN, which mostly makes hiking shoes, has a great waterproof steel toe work boot, the Flint. This one comes in ankle-height of 6” rise. If you work in a warm climate, you could consider the appropriately-named Atlanta, which has a bit more mesh outer, but is still waterproof. Both have an asymetrical steel toe that is enveloped by an integrated rubber toe (no glue means longer-lasting). In case you have broader feet than average, KEEN is known to have roomy shoes, width-wise, and a wide version if you need it.

KEEN Atlanta Cool Steel Toe Boot

KEEN Atlanta Cool Steel Toe Boot

You can disregard the old myth about steel toe boots taking your toes with them in the unlikely event that they do get crushed; Mythbusters (an incredibly scientific institution, to be sure) tested it and proved it false. That said, the likelihood of a composite toe taking a hit that shatters it is extremely low.

Composite Toe

Composite toes are made of a mix of materials like Kevlar, carbon fiber, plastic and/or fiberglass. For most job sites, composite is more than enough protection and it has additional benefits. Composite toes are lighter than steel, which makes them more comfortable and easier to wear all day, day after day.
Plus, metal conducts heat, meaning steel toes suck the heat out of your feet in the winter and horribly insulate them in the summer. Composite toes, being non-metal, won’t have this issue. Another benefit to a non-metal toe is for electricians or those on a site with live wires, since it will have much better electrical resistance that the highly conductive steel-toed boot.

Timberland Boondock Composite Toe Boots

Timberland Boondock Composite Toe Boots

Timberland makes a great composite toe called the Boondock, which comes in 6” and 8” rise and a regular and insulated versions. In addition to being composite (which isn’t conductive), these boots make electricians and contractors working around live wires even safer with additional protection against electrical hazards built right into the sole. The sole is combination welt and cement and has deep lugs for extra traction. These are great winter boots. All are treated waterproof leather and an additional waterproof membrane. As with any leather work boot, be sure to treat the leather regularly to maximize the lifespan of your boots.


If you live in Texas, winter weather is probably a minor consideration, but in Boston or Chicago, the difference between winter and summer is astounding. It means you’ll almost certainly need two sets of boots: 3-season and winter. In some places, you may even want a third pair for wet, warm weather.


Working outdoors in winter weather is uncomfortable and often comes with significant risk. It’s unlikely that frostbite or similar cold-related trauma will be an issue, especially if you are moving around all day. However, with winter comes snow and ice; if you work on open sites or outdoors, especially on rooftop, having a grippy sole is critical for your safety.


Waterproofing can come in a few different forms. The first, the oldest, the classic is leather. Leather can also be treated specially to give it additional water resistance. The other way is synthetics that are specially treated to be waterproof; sometimes this waterproofing will be merely a membrane between the outer shell and inner padding of the shoe. Gore-Tex is the best known version. A combo of both is often best.
Waterproofing isn’t just for winter. All year long, depending on your location, you may experience wet weather and need protection without superheating your feet. The KEEN Atlanta discussed above is a great example of 3-season waterproof option.


What does make a waterproof boot an explicitly winter boot is insulation. The latest version of the Columbia Bugaboot includes what they call Omni-Heat technology. In addition to the standard 200g insulation, the boots are lined with breathable thermal-reflective lining that retains warmth as low as -25°F. The leather and nylon construction with seam-sealed waterproofing is good enough to hike Everest, so it should cut it on site.



While not associated directly with your shoe choice, you should also consider getting inserts. Whether it’s Superfeet, Dr Scholl’s or custom orthopedics, inserts can make a huge difference on your feet, knees and back if you work on your feet all day. If you want to use inserts, be sure that you buy boots with room for them. It can help to get boots with removable inserts, since the usual thin piece of foam doesn’t generally offer much additional support anyway.

Superfeet Inserts

Superfeet Inserts


Having comfortable feet all day starts with the right socks. Socks provide cushioning, but the right sock can also improve your circulation and wick away sweat. Everyone from runners and hikers to survivalists preppers will tell you that “cotton is rotten.” Cotton absorbs moisture (such as sweat) and holds onto it. This does two gross things. First, it makes your socks heavy, wet and uncomfortable. Second, it grows bacteria which makes your feet smelly and can lead to infection.
The solution? Technical synthetics or wool. These socks will pull moisture away from your skin and disperse it across its surface, which allows it to evaporate faster, keeping your foot dry and comfy.
On the synthetic side, I would have to recommend REI Coolmax hiking socks. There’s both midweight and ultralight and they come in ankle and crew height, so you can get whatever you need. If you prefer wool, there’s nothing like Smartwool. Ethically sourced and of the highest quality Merino sheep, they neither itch nor smell. Which a range from ultra light to extra heavy weight and micro to over-the-calf height, Smartwool socks can be worn all year round and with any shoe.


Smartwool, REI and countless others also carry what are called liner socks. These are socks inside your socks. If you are working in frigid conditions or tend to sweat a lot, liner socks are extra effective at drawing sweat away from you and pushing it to your socks to get evaporated away. This means your feet stay drier and more comfortable, especially in extreme weather conditions.

Alternating Days

If you work in wet conditions or you sweat a lot, you might want to consider getting two sets of boots and alternating. Ensuring that your boots are dry in the morning when you put them on is a big help in avoiding discomfort, smell and issues like athlete’s foot.