You're nothing in this game now without a pair of brown boots. At least that's how it seems from all those cool guys on t'internet. I can sort of see their point – it's a timeless enough style, and we've all had Timberlands or Oxblood DMs in the past (haven't we?)
So, in a vain attempt to drag myself up to date, I asked the good people at Alpinestars if I could try out a pair of these here Oscar Twin Drystar boots. Crazy name, crazy boots, huh? Oscar is Alpinestars' retro brand, named after a range of boots in the 1970s which stemmed from a fashion show entry. Twin is the name of the boots. Drystar is Astars' own breathable waterproof membrane.
So this pair of brown boots has a waterproof membrane (very useful considering the current state of precipitation round here), plus the security of a proper Alpinestars boot protection package: reinforced toebox and heel, plus armoured discs on the ankles. So, they'll be more waterproof than a Timberland, and massively more protective than your old Doc Martens. And I know it's hugely subjective, but I think they look really good.
I've been wearing them for a month or so, both on and off the bike, and after a tiny heel blister or two, they've bedded in nicely. No-one in the pub has pointed and laughed (well, no more than usual), and on the bike, they're comfy, and give some peace of mind on the protection front (although there's no shin protection of course). I've not tested the waterproofing in proper rain yet, but they've coped easily with mild spray from a wet road. These will no doubt be my 'cool' riding boots for this season, so I'll keep you posted on how they do.
All this, for about £160-180 (street price) seems very decent value indeed. I've seen Timberlands selling for not a lot less than that. Riding with the cool kids, plus almost all the protection and weatherproofing of a 'proper' bike boot? What more could you want?
More info here.