I have slightly wide feet (9.5 2E) and these fit great (I got the size 9.5 W). I spent two weeks breaking them in, and used mink oil just in case. Water proofing seems to be holding up fine and they're warm enough in what passes for cold weather in California (40-ish degrees at night). I'm going for a week to Korea, so if I don't complain later, then you'll have to assume they worked great.

UPDATE - just got back from Korea and the 2018 Winter Olympics. Shoes were sufficiently warm, whether with thick cotton or wool socks, and stayed waterproof without any problems (though I did coat it with mink oil beforehand). The boots also had good traction on the snow. Held up to a week of hard wear. Very comfortable. Overall, excellent boot especially as i got them on sale.

I am very sad to say that Timberland quality seems to be falling off a cliff as of late. These ARE NOT LEATHER, but a synthetic material that does not age well. And while synthetic is in the item description, what is not listed is the POOR CRAFTSMANSHIP, LACK of ATTENTION to DETAILS and terrible Quality Control. Please see my photos and ask yourself, (1) 'How could these pass inspection?' and (2) How could Timberland sign off on this (put their name on) these? Mind you, these photos are not of boots that were worn and frayed... these photos are of the boots straight of the box just as you see here. The stitching is all over the place, the waterproof tab sewn through and crooked. I used to be willing to pay good money for Timberland's because you knew you were getting rugged, American made footwear with a tradition of craftsmanship. Sadly, this is not the case with Timberland anymore as these are made in China from synthetic materials and bear no resemblance of Timberland of even 10 years ago.

I needed a pair of hiking boots to replace the Keene boots that were only 1 1/2 yrs old but not only lost their waterproofing in the first six months but had a weed stalk in the field go right through the side and almost break my skin. This was the second pair of Keene's that had gone bad in just over a year and, at $130 I was getting tired of replacing them.

Started looking at reviews and found these. They have a large toe box with plenty of room. Before I took them out I took another reviewers advice and put a coating of Mink Oil on them. They were comfortable but I knew they'd take a little break in. I now have about three or four miles of walking through the fields and surprisingly they seem to be breaking in rather quickly. I usually put on about 500-700 miles a year.

One note, if you're looking for hiking boots that will give you really good ankle support these ARE NOT for you, look elsewhere. These are for easy hiking, fields and roadway. When I got them I first put in a pair of Dr. Scholls and that went a long way toward making them immediately comfortable.

If I remember I'll give an update in three or four months.

UPDATE: Jan. 6, 2018 - I've now had a chance to wear these for a while including the recent snow storm and frigid temps (at least for us). We got 5" of snow, temps this morning, when I took the dog out, we're 4 or 5 degrees with a windchill of -8. I had been wearing wool socks with these and my feet have stayed warm and dry on a 25 to 35 min. walk through the fields. This time, with the snow and frigid windchill I decided to try just summer cotton socks. Bear in mind I'm a 70 year old with diabetes, which does affect circulation, so I'm pretty sensitive to cold and heat and the comfort of my foot wear. (I walk approximately 3 miles a day with my dog, even in the snow and cold unless it's too much for her.) So, the results of a 20 minute walk were still warm and dry feet. I could have gone much further but Harley was getting snow turning to ice between her toes every few minutes and we'd have to stop and I'd have to remove it.

Bottom line: When I received these boots I put in my Dr. Scholls insoles from my previous pair, rubbed in three coats of mink oil on dry days (which I think was key to waterproofing) and started walking. I've found them to be far more comfortable than the Keen's I was previously wearing. I don't walk as much as a lot of people, about 25 miles a week, but they're doing well for me for field and neighborhood walking.

2/9/18: I like to keep folks updated on important stuff: If you want a pair of boots to wear, every day, and forget when you take them off, look elsewhere. Because these are leather they require a LOT of care. If they get soaking wet do NOT continue to wear them the next day, you'll ruin them. I've found that when mine get soaked from walking in the pouring rain, in the field with my dog, I wipe them clean with an old towel, put shoe trees in them to keep the leather from shrinking and set them aside where there's a flow of air to let them air dry. Do not try and force dry them with hot air, you'll ruin the leather. Putting them a few feet away from a fan seems to work okay or just let them sit. While they're drying I use an old pair that I kept. After they have dried completely I retreat every inch of leather, paying particular attention to seams and around grommets, with mink oil, let it sit and dry then retreat again.

Is the above a pain? Yes it is but these appear to be quality boots and you need to take care of them, not let them get muddy and wet and toss them in the corner for the next day.

Unbelievable! Super low qulaity and weird finishing!
Something you never expect from Timberland!
China made and low quality!

I ordered these for my husband who has wide feet with a pretty flat arch. He's incredibly hard on his shoes and he needs shoes that are supportive and can really stand up to everything he puts them through. In this instance, he needed waterproof boots and I ordered these despite being concerned that they might not be waterproof enough. I'm happy to say I was wrong - these are great! Not only do they look great, but they held up to him hosing down a ship deck and soaking his boots in the process and his feet stayed dry!
The fit is great and he needed zero break in time. They're now his go-to shoes whenever he's going anywhere and he's says they're extremely comfortable to be in all day with no soreness or irritation.
I'm really pleased with how well these are made, and how well they're holding up to heavy, regular use. They still look brand new, and if you knew my husband, you'd know that's really saying something!