I didn't even know BN had a fashion section. COOL!
I've actually got a lot more experience in this field than I do with fragrances since I took an interest in this a couple years back as opposed to a couple months back.
First off, let me say I'm biased against Dr. Martens. They thickness of the soles, and the yellow tag, along with their overall construction make them look cheesy to me. I should also add that Dr. Martens have kind of been co-opted by the ladies. I still see men wearing them but I definitely see them more often on women where I live (NYC and the surrounding suburbs).
Clarks on the other hand are fantastic. They look great, both with jeans and chinos. In fact, I'd say that if you're a bit more avant-garde you could even get away with wearing them with shorts. They're some of the most versatile shoes a man can own, second only to a pair of simple almond brown wingtips. Plus you'll never see a lady wearing Clark's. Desert boots, yes, but rarely is ever real Clark's.
I had a pair of the Beeswax Clark's a year or so back, and loved them but they fit kind of funky. Be sure to try them on, and definitely size down either a half or a full size as they do run big. I'd recommend beeswax over suede since I think it's a bit more versatile, but either looks great.
Personally, I don't wear my Clark's anymore because they were a bit too long and because of the length, the crepe sole, while very comfortable, had a habit of getting caught on the ground and making me stumble while I walked. I got myself a pair of grey suede desert boots from Kenneth Cole (yes, grey shoes. they work more often than you'd think, trust me) and I love them to death. So I should point out that Dr. Martens, while not my favorite shoes, are distinctive. You won't find a designer copy-cat unless you're looking for something entirely different altogether. Everybody and their brother makes a pair of desert boots that look and feel roughly the same if not better than Clark's. So if you decide on desert boots (an I think you should) don't limit yourself to Clark's, go to Nordstrom's or Macy's in the fall when they go back on sale and try on desert boots form a few different brands.
I do have to begrudgingly give Dr. Martens one point over Clark's; They are infinitely more functional. I'd never think to shovel snow or walk the dog in a rain storm while wearing Clark's. Dr. Martens on the other hand could take the abuse and then some. Still ugly as all hell in my opinion.
And skip Tims. If you decided you wanted a pair of work-boots Timberland offers a great value in terms of combination of form and function, but you'd be infinitely better off getting a pair of Red Wings. Finally pulled the trigger on a pair last fall. The break-in hurts like hell, but once that's over they're comfortable, strong, highly practical, and attractive to boot (pun intended). Because of Red Wing's resoling policy you'll never need another pair of work-boots for the rest of your life. But I digress...