I have the Wolverine 1000's and a pair of OSB cap toes that were sent back to OSB to be resoled with a Dainite sole. My OSB are the natural chromexcel. The Wolverines were comfortable right out of the box and built on a fairly sleek last. They look a little dressier in my eye. I'm usually a size 10.5 in dress shoes and wear a size 10 in the Wolverines and added a cushioned insole. The OSB took a few days to break in, but nothing major. They fit TTS and don't really leave me room for an added insole. The toe of the OSB is a little more rounded, so it does fit wider and doesn't have the same sleek look - although it looks damn good! The natural chromexcel, the cap toe, the broguing, and the natural colored midsole really make the boot stand out and it just seems a little better built in my mind. The Wolverine is a very solid boot, but rather plain and doesn't seem to be as well built - although I'm certain it will last me for years as I have many pairs of footwear.
I would also consider a pair of Red Wing Beckhams in black.
http://www.amazon.com/Red-Wing-Beckman-Cherry-Featherstone/dp/B00542X6IW/ref=cm_cr_pr_product_top
I have a pair in the black cherry color. I got mine for about $175 a few years ago and wouldn't pay full retail for them, but I like my pair quite a bit. In a way, they are my "beater" boots. I wear a size 10 in this boot and still have room for a padded insole. They fit a bit narrow, so if you have a wide foot, I wouldn't consider the RW's. They also took a bit longer to break in than they other two pairs. I like the commando sole.
Shfle, thanks for the link. I'v never heard of them before. Do you know of any stores that carry them?
They're one of the few English shoe/boot makers who are still making things by hand in England. It doesn't look like you'll find this model stocked anywhere though, as it looks to be literally hand-made to order, with an 8-10 week delivery estimate for the UK, so will be a bit more if you're elsewhere