Customer Reviews: Timberland Men's 88580 Mt. Washington City Chelsea Boot,Black,9.5 M
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on September 30, 2011
I'll keep this simple:

1. These shoes are the most comfortable shoes I've had in years.
2. They are high-quality (If you use the front and back loops simultaneously while pulling on the boot, they won't break. It is also easier to get them on that way.)
3. Wear long socks when you wear these because there will be high-ankle rubbing because a.) you shouldn't wear short socks with these anyway, and b.) the elastic needs to be tight to insure a better fit.
4. They look rugged yet sleek--a very versatile look (not as shiny as the picture)
5. They have excellent gripping capablity. People need to know, no matter how deep a shoe's tread is, there will always be a slipping hazard on ice. These have great stability on gravel, pavement, snow, etc.

I hope this helps. Enjoy the boots, I highly recommend them.
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on January 29, 2010
I previously owned a pair of brown double gored Timberland boots in almost a previous version of this style. They had a hard spot where the heal ended. This created a pressure point in the bottom of the foot and the shoes could not be worn for long periods of time. It was so bad, I am convinced then never quality tested this boot. So I got an insole. Problem solved.

These new boots have a better insole, so at first I was happy. But after wearing them for a while, I found that the top of the tongue was uncomfortable pressing on my shin. It feels like at then end of a day of skiing in plastic ski boots. I wondered why the other boots didn't do this so I took a look. The old boots had padding around the inside edge of tongue and the back inside edge where your ankle exits the boot. Timberland obviously knew that these pads are needed in this style boot, because they included them in the previous version. But they cut them out in this version, presumably to save money. At these prices, I expect better. Oh, and these new lower quality boots COST MORE than the old ones, which had the padding. COME ON TIMBERLAND! Give us quality! I admit that your boots are the most attractive. But make the wearable and long lasting, and your boots will earn five starts and create loyal customers.
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on September 3, 2009
This Boot by Timberland is a re-badged version of their Torrance Chelsea Boot. Price online is about equivalent to what you would pay at a department store. So I purchased mine at a department store. Timberland used pretty good high end leather to make this boot. Comes in a matte finish. Touch the leather and you will know. These boots fit very true to size so order your exact size. If your a size 11, then order a size 11. Do not order a 11.5 Unless you like wearing your boots very loose. These boots have a real comfortable inner sole so your feet will feel comfortable. This is my third pair of Timberland boots and by far it is the most comfortable boots. They go great with a pair of dark blue jeans. This is a pull-on boot and not a zip up boot, so you need to put more work into it, to put it on.
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on November 29, 2010
These boots blew away all expectations I had after ready reviews from this site and others. If the proper research is done, these boots will fit you perfectly. Here is what you need to know to be completely satisfied with your purchase. 1. If you wear a 9.5 in shoes, order a 9 in these boots. They fit a half size large. 2. Wear high top socks with these boots. Reviews from other sites complained about how the leather rubbed their lower calves sore, but a boot of this type was not made to be worn with gym socks. If they feel roomy, try buying thicker socks. 3. Give these boots time to be broken in. The leather is beautiful and sufficient quality, so allow them time to fully form to your feet. Other reviews from different sites complained of comfort, but I imagine they didn't quite understand the satisfaction patience can give someone concerning well made boots. 4. Personal tip: wearing a dark colored, boot cut style blue jean with these boots will leave you very impressed.

On a final note, you will be skeptical at the first sight of them due to the elastic that is found on both sides. If you are concerned with looks, wear a good fitting boot cut blue jean. If you are concerned with them being waterproof, rest assured that you need not worry and the elastic holds up well. An excellent boot, and best wishes to you all.
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on May 1, 2013
This boot fits my needs very well:
1. Must be dressy enough for work - looks good with slacks.
2. Must be relaxed enough for casual day wear - looks good with jeans.
3. Must be able to walk LONG distances without foot stress - I'm in my 50s and can walk several miles from work to home without calluses or discomfort.
4. Must age well so that it stays presentable for work through out its life.

I've worked for several California corporations and have never had anyone look askance at my footwear, but I have had coworkers complement the shoes and ask for brand name when they hear how much walking I do in them.

Other "comfortable" dress shoes either aren't formal enough (they look orthopedic), or they damage my feet if used for walking (either too heavy or improper sole for walking), or they don't age well (soles wear out, leather tears, etc).

I wear the Chelsea 2 to 3 times a week, walking 5+ miles every day. A quick polish every month or so is the only maintenance. Each pair has lasted 3 years or better under this regimen. (I replace shoes when they are not presentable, which is well before they break.)

However, true walking/dress boots is a recent trend. There are several competitors that have sprung up in the last 5 years and I have not tried those due to my contentment with this brand, so I might be missing out on an even better design out there.
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on September 21, 2014
These are really wonderful boots. I wore them with a suit today and they looked great. I work in education and I'm on my feet all day. These Timberland boots really meet and exceed my expectations. The boots fit well and the leather is pliable to move with you and not stiff. I like the tabs on the front and back of the boots to pull them on and off. The soles are stiff enough that you don't feel every pebble when you are walking, but they are not so stiff that they feel too rigid. They are just right. When I have free time I also use these for walking. In average week I will walk another ten miles besides the walking at work. They are nice for all sorts of weather. The best part is if you get some dirt on them they wipe off easily. These are boots for a person who needs support and is moving all the time. I highly recommend them. The best part is they slip on an off in an instant.
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on December 23, 2014
I first want to say that I LOVED, I'll repeat, LOVED these boots. Unfortunately I've owned 2 pair in the last 4 years and have only gotten 1 year of use from each. The problem? The rubber tread. Each pair was worn down so badly that holes began to emerge, making the waterproof utility of the boot obsolete. The problem is that there is no barrier between the rubber tread and the insole...meaning if you step on a nail, etc. it would go through with absolutely no problem. Picture the material that makes a basic Halloween mask; that is the thin rubber that keeps your insole from the outside world.

That wouldn't be such a problem if A.) the treads were repairable by a cobbler or B.) if customer service was helpful. They are fantastic boots and look sharp when they aren't full of holes. Once the tread begins to wear you have no option but hope that Timberland will replace them (possibly due to defects) or trash them. I've been told by different cobblers that these types of tread are not repairable and to try to reach out to the manufacturer, in this case Timberland customer service. I spoke to 2 different people; the first person at the help desk almost made me laugh while the 2nd transferred me back to the main auto-attendant menu, only for me to get transferred all over again. The first lady at the help desk said that because the tread wore away the warranty would not be applied...leaving me in utter awe as that was the part of the shoe that had failed on me twice. I relayed what the cobblers had told me and she informed me that Timberland does not repair shoes. I tried to go the next in what does everyone else do if they have shoes that neither cobblers nor Timberland can fix. Her answer was to throw them in the trash. That would be fine except for $150, or roughly $300 in 4 years, I shouldn't expect to completely throw away a pair of boots. I've owned Red Wings, Wolverines, etc., and granted those were work boots, but boots and the Timberland name should imply quality and longevity. At the very least a helpful recommendation on how I can get them back to their original self again.

I wish I could give these a great review as I truly loved the look, feel, and functionality of these boots in rain or snow. I've walked miles and miles with great comfort. But the tread just doesn't last...and I would give a 5 star review if it wasn't for 2 pairs doing the exact same in a short amount of time. I'll unfortunately be looking for the same style of boot from a different company that provides products that will last. Bad taste in my mouth regarding this model and Timberland in general.

*If the tread were more durable I would be a returning customer for life*
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on January 18, 2013
Hey, Oldtimer! Tired of hunching over to tie your shoelaces after airport security? Envious of the younger dudes just slipping their laceless boots on and off while you hoist your hinder and grunt? Well, here's the answer! You too can be insouciant; as long as your cuffs cover the boot tops, these Timberland Boots will look just like the old-fashioned black business shoes guys your age are expected to wear.

They're sturdily made, besides, and remarkably comfortable in fit. The only irritant for me is a chafing at the very top of the boot if I wear socks that are too short. The soles are durable and the whole boot is reasonably weatherproof. They're not made for ballroom dancing, of course, and they look a trifle funky with a tuxedo.
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on April 18, 2014
I was impressed with these boots right out of the box. The feel of the leather, the overall look, the design of the sole, and the Smart Comfort insole all combine to make for a great boot. These boots fit me perfect, they are true to size (13D) and are a snap to get on and off. They provide amazing support and walking in them is a joy . Be sure to wear a mid-calf sock with these. These boots are a winner!
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on January 30, 2013
I liked Timberland's rendition of the Chelsea Boot so much, I bought a 3rd pair. Granted, it's the 3rd pair I've owned in the last 2 years. I wear them practically every day. They are very comfy and stylish as well. I can't help but emphasize the comfort and style the boot looks. Unlike other Chelsea Boots, these look just right. Other manufacturers seem to have a rendition of a Chelsea Boot that looks too stiff or very 'blocklike'. The straps in the front and back of the shoe help assist with putting the boot on with ease. Definitely worth the purchase.
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