Back in 2001 I purchased a pair of black Rockport Umbwe Trail boots. At 18 years old I thought £180 was a bit steep, but they just looked amazing, and I heard that they were very good quality.
I recently read that these boots were worn by lots of teens back then, but I never came by many. I guess they weren't a Surrey thing.
I wore these boots daily, including long country walks and in the wettest conditions. They never ever leaked and had the added bonus of looking good.
It's nearly 14 years later and they still look almost new! Obviously in that time I had other boots, including Timberlands, but they always perished; the uppers quickly got tatty and the soles always wore out after a month or two, so I kept going back to my trusty Rockports. £180 turned out to be a massive bargain.
The only problem with a quality item is that it often outlasts trends, unless of course the items are timeless, but I don't think this style of boot is. How annoying then that timeless styles often fall apart in 5 minutes.

So this winter, can I wear my Rockports?

Yes, yes you can! Slightly different style to you, but I have a pair of Dubarry Galways which cost £300 about 5 years ago. A lot of people laughed, commenting about how expensive they were for 'a pair of leather wellies'. But they have lasted and lasted me. Comfortable, completely water/snow/mud proof. I now live in the ME so no need for such footwear, but I cannot wait to get back to the UK and it's inclement weather just so I can wear them again.

They look great. I can see why they have lasted you. Perhaps ill chuck them on again this winter. If only the style came back though, then I wouldn't be so self conscious.

Don't be daft! Or maybe style doesn't bother me so much as I'm getting to the age that comfort is more important than anything else

You could start a new trend?!

I still wore mine up until 18 months ago, every winter when I did home care. they're still in my loft, in the same condition that my OH bought them in 7 years ago! They're so comfy too!

Who cares about whats on trend, its all about comfort!!

I'm of that age too, but sadly I still have that mindset of needing to conform, which I know is rediculous. Rockport Umbwe's certainly isnt conforming.

It's not an age thing. I'm 23 and I'd much rather wear something that gets me to work with dry feet and without falling over in the snow/rain/whatever. If needs must, I can always put something more fashionable on when I get there.

Last time it snowed I had this girl get on my bus in heels???!! I don't understand some people's logic at all.

If they're in a reasonable condition, are comfortable, practical and still fit, you should absolutely wear them. Who cares what is or isn't 'on trend'? I guess I too am of a certain age when such sensibilities are ludicrous....

This is the condition http://goo.gl/asrPQl

Wow, you've really looked after them - they're in great condition! Personally I wear my footwear, particularly boots, until they fall apart. When they become 'unfashionable', I may rest them for a few years/seasons, but I always go back to them.