I work on my feet all day, a warehouse environment in the winter and outdoors in the summer. After 5-6 months of constant use, I have to say these things have held up well-ish. I do have slight separation of the sole at 1 side but nothing bad. Boots where I work usually don't last past the year mark before needing to be canned so I'm not sure if these will make it to that point either. The one big thing that took some getting used to is the weight, which only takes about a week to adapt. After a long day in these things, it feels like walking on air when I slip into my athletic shoes. As for the waterproof, stand in as many puddles as you want, yes it is indeed waterproof. Just remember it's only an ankle tall boot though, too much splashing will cause water to soak from the top of your socks all the way down to your toes. How about the steel toe? Well, I work with very heavy poles that I have a habit of resting on this boot without feeling a thing... and I also kick stuff a lot with both the front and back of my boot. Yet my feet still manage to feel pretty good at the end of the day. These are much more comfy than any other boot I've owned or tried on.***Durability Update***9-10 months of use and this boot was absolutely done. Tread on these boots is now mostly gone and now just a flat slick surface so it's impossible to get any traction. Back of the heel inside the boot has rubbed all the way into the plastic, giving me cuts on my back foot. The waterproofing worked for up to probably 6 months before I started noticing my feet constantly being soaked from sole high puddles. I would treat the boot every month to keep the leather conditioned yet the leather just looks like.... let me be honest, I'm embarrassed to wear these to work. The sides of the sole still don't show a terrible amount of separation so that could be listed as a plus?I consider these to be great boots. I've also got a few guys on site addicted to them as well. I work construction, so I'm on concrete, gravel, rebar, mud, sand, and ladders all day, everyday. I'm still wearing the ones I purchased 17SEP11. Usually boots last me 9-12 months. I weigh 165, and if you look at the caption of the back of the boot, I'm just getting to the low orange stripe on the sole of the boot. The insole is still very comfortable.Some of the fellas on site with back trouble, have said that they feel a noticeable ease in back pain. I used to wear Dr. Scholl's Memory Fit Work Customizing Insoles in addition to the insoles that come with other boots, but I just use these with the supplied Timberland insole only.The boot is ugly now, but just as waterproof and all over comfortable as they were on day one.I purchased a second boot, because you should always keep one in the chamber; but it is still in the box waiting to be put to the test. I expect this boot should last me possible two more months. The sole is wearing pretty evenly, so it is not causing me to walk lop sided, pronated, nor supernated.It is my opinion that this is an excellent boot. It is more comforatable than Dr. Maarten, of which I was a huge fan until they changed the shape of their lace to toe boot.I'll end my rambling with pointing out that I find these boots to be sized small. I wear size 11 (European 43) with all other shoes and boots, but wear a 12 in these.I'm buying another pair for another workmate this instant.I am not a Timberland employee or representative.I am Milo Ruiz, and I approve this boot.Im a High School Wood\Metal teacher who also takes students on camps and rides a motor bike so I needed a waterproof boot that's comfortable when on your feet all day. I had a pair of the Timberland Titan Pro and wore them 5 days a week for 12 months before purchasing these.Out of the box they weigh twice as much and although the lacing system on the top 2 loops can be permanently fed through a hole - I have to say they're nothing compared to the Titan Pro.- The sole is coming away around the high wear area.- The patch on the tongue over the arch of the foot prevents the laces pulling the lower part of the laces tight- You know you've worn them at the end of the day as compared to the Titan Pro.The boys in the class laugh when we're concreting at school and ill kick a timber stake out of the form-work but that's all they're good for except standing on nails. 4 months and I'm thinking of binning them.From my original five star review, down to a one star review.Heavy, far too heavy; Danner boots are much lighter. Size is off by one size too large.I take a size 10 boot; these are larger than they should be for a size 10. Uncomfortably loose, even while wearing heavy boot socks.Felt good at first; but after wearing for 2 months on hard surfaces, finally realized these boots were destroying my feet.Both my feet, specifically my heels, were feeling the pain until I went back to my old Danner boots; and realized these Timberland boots are actually very bad boots to wear for any long period of time.Most boots break in with usage, and become more comfortable; these became worse with usage, and more uncomfortable.Going back to Danner boots; these were a total waste of my money, since it's too late to return them.However while Timberland may have got me once for the cost of these; my first Pair of Timberland PRO boots is also my last pair of Timberland PRO boots, in fact this is my last of Timberland anything. Go to their own website and read the negative revues on this product; I should have before wasting money on this junk.