It saddens me to report that this boot was modified by Timberland and made much worse. I totally loved the previous version. Here are my findings after buying this latest model:
PROS:
Nothing was improved upon. I will say that, at least, the boot is still waterproof thus far.
CONS:
The worst change is in the shank supporting the middle of the foot. Before, the Rugged Street Chukka was a lot more rigid in the midsole area. It seems now that a weaker, more pliable material has been substituted. This new shank material allows uncomfortable pronation, or twisting and bending, of the shank when stepping onto uneven surfaces. I'd have paid more money if they'd left this design feature the same.
Next, Timberland raised the height of the toe box noticeably. A little might've been okay, but they went overboard for sure. I bought this boot in the correct length and width, but my foot still slides forward due to the tall height of the toe box. Also, the excess height of the toe section makes this boot appear more like a work or strictly outdoor boot. Previously, the design was much more urban and versatile, due to a shorter toe box. All change is not good.
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I bought a pair of these in 14 W. Usually I try on any pair of shoes I buy, but it's almost impossible to find anything stylish in my size. They are awesome, and I wear them a lot, but definitely not for long periods of time. Most W and 2E width shoes I've bought fit perfectly, but the Timberland Wide seems to be narrower than most, so beware if you need the extra width. I still get my feet in fine, but I also usually where Orthotics, but the shoes are too narrow for them. All in all they're a good, durable shoe, just beware of sizing.
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