I have some different needs for work boots than people who are outside all the time. My requirements have shifted over the years as my lifestyle and living situation changed – and let me tell you, finding the perfect boot is like searching for the Holy Grail, except with more blisters and buyer’s remorse.
The NYC Studio Days (not studio 54, way before my time): Red Wing 8249 Glory
Years ago, when I was working as a studio manager for a film production company in NYC (worst job I ever had – but that’s another story), I met a guy who introduced me to the Red Wing 8249 Steel Toe Moc Toe Supersole. I believe I found these online again with just a slightly different tread pattern. They don’t have the padded ankle, which I actually preferred.
These boots were absolutely awesome for long days working on set, moving flats and equipment, never having to worry about dropping a heavy piece of marble or steel on my toes. They were also sharp enough to wear out for drinks after the shoot wrapped or even to the bar on the weekend. Talk about versatile – from film set to cocktail hour without missing a beat.
These were the best boots for that time in my life. The only downsides? They weren’t waterproof, the soles were slippery in snow, and they couldn’t be easily slipped on or off. This became a real problem in airports and when you buy/build a country house where taking your shoes off every time you come inside is mandatory. When you’re going in and out multiple times per hour, lacing up boots gets old fast. I just dug them out and I’ll look for elastic laces to see if that helps.
The Vibram Experiment: Red Wing 4183
I thought the lack of aggressive tread on the 8249 Red Wings was an issue, so I was thrilled when Banana Republic started carrying the Roughneck Heritage 4183 moc toe with a Vibram lug sole (Red Wing appears to carry this model again). I bought the 8.5 since it was the same size I wore in the 8249, but I should have gone with the 8 since there was no steel toe taking up space.
The lugs just ended up being a problem – they got clogged with mud and dirt constantly. Since it wasn’t waterproof, it couldn’t really be worn in rougher terrain anyway, so the 8249 remained the superior boot. Sometimes simple really is better.
The Waterproof Quest Begins
For working around the house, I’m always in wet and muddy areas, so I needed something waterproof. When we were building the house, I opted for 8″ Red Wing Dynaforce waterproof boots. These weren’t slip-ons, but that didn’t become an issue until later. They held up well – I still use them, but only when I know I won’t have to come inside for some time.
When we finished the house and I had to take my boots off every time I came inside, I knew I needed a different footwear solution.
The Chelsea Boot Discovery: Timberland First
I actually discovered the joy of Chelsea boots through a Timberland Chelsea boot that I loved so much I bought it in both black and brown. It was really comfortable to wear and great for traveling, but it wasn’t a work boot – it was a bit too dressy for what I needed. The brown leather ended up cracking really badly over time, which was disappointing.
But that Timberland taught me how convenient the Chelsea boot style could be. The slip-on convenience was exactly what I needed for my constant in-and-out lifestyle. I just needed to find the same convenience in an actual work boot.
Finding a Work-Ready Chelsea: Avenger Wedge
I looked for an inexpensive waterproof slip-on Chelsea work boot, hoping to find something with a moc toe. I was unsuccessful, but I decided to try the Men’s Avenger Wedge Chelsea Leather Waterproof Boot. Initially, I didn’t want a white wedge sole, but this seemed to be all that was available. After I got the boots, the white sole grew on me – which might have been a bad thing because I later noticed hipsters had started wearing white sole boots. Great, I was accidentally trendy.
Anyway, the boots ended up being a great purchase. The 6″ height made them easy to put on, and most importantly, they were waterproof. You couldn’t just slip them on – they needed to be pulled on – but it was still so much more convenient than having to tie laces many times a day.
The only drawbacks: the white sole turns green when mowing with a walk-behind mower (charming), and they didn’t hold up that well as the seams started coming apart after a few years. I guess all that taking on and off contributed to the wear.
This is a great site for Work Boots
The Moc Toe Tall Boot Experiment: Iron Age Solidifier
After the Avengers needed to be replaced, I started on a quest to find a moc toe slip-on and all I could find was the Iron Age SOLIDIFIER MEN’S BROWN 11″ PULL-ON MOC TOE WATERPROOF WORK BOOT. I had high hopes for this boot.
It’s a nice boot with toe protection, which is nice to have (although it does rub on your toes a bit). The problem? It’s just a little too tall and wide at the top for my needs. You need to have wide-leg pants for them to slip over. Really wide-leg pants aren’t my preference because with my small feet, I start to look like a kid playing dress-up in dad’s clothes. This probably isn’t an issue for most people, but if this boot came in a 6″ or 8″ height, it would have been a magical find.
The Compromise Boot: Georgia Boot AMP LT
This was going to be my hard-use work boot, but I decided to get another work boot to wear to kids’ sporting events and to run errands, so waterproof was still important. Easy on and easy off remained crucial, and I decided to stick with the white sole since it had grown on me and I didn’t see very many people wearing white sole boots in New Paltz (we’re not Brooklyn, after all).
I tried to get the Danner Bull Run Chelsea, but my size was sold out and it was on the pricier side,
so I opted for a sale pair of GEORGIA BOOT AMP LT WEDGE WATERPROOF CHELSEA WORK BOOT. When I got these boots, they seemed a little narrow, but I decided to keep them anyway.
These boots are… OK. They’re not as comfortable as I hoped and are not that good for a lot of walking, which is one of the things I need them for. I use these boots as my around-town boots in inclement weather so I don’t have to wear my chore/rain boots, and ideally for walking/sightseeing on holiday. I may switch these over to my mowing boots, but haven’t decided for certain yet.
The Bottom Line
For people who don’t have to take their boots off and put them back on constantly, this is probably not that relevant. But if you spend your time going between indoors and outdoors, these experiences might help you.
My preferred boot is still the Red Wing 8249 Steel Toe Moc Toe Supersole, but it not being waterproof or slip-on limits its usefulness for me at this point. I would love a waterproof Chelsea version of this boot – that would be my holy grail. The Red Wing Classic Moc could also be an option, but it’s not waterproof or slip-on either.
Current Brands I’m Considering
Here are the latest brands I’ve narrowed down: Iron Age, Georgia Boot, Sorel, Danner, Handpoint, and Avenger.
Any I missed that aren’t obscenely expensive?
Red Wing, please release a moc toe waterproof Chelsea SuperSole! I’m begging you here.
A Quick Note on Sizing: Don’t assume that because one pair of boots in a certain size fits well, another pair of the same model and size will fit the same way. I’ve had boots that were torture devices and others that were perfectly comfortable – same brand, same model, same size. Quality control varies, leather stretches differently, or maybe it’s just boot karma. Always try them on if possible, and if ordering online, make sure you have a good return policy.
Even that's Odd 
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