My old Red Wing lace-ups are splitting apart at the seams, and I’m now in the market for a new pair of shitkickers. Black leather is pretty much a must, as is a safety toe, but I’m torn between lace-up, engineer, or harness, in lengths between 9" and 17". I’m also brand-shopping, looking at Chippewa, Wolverine, Dr. Marten’s, and Underground. So y’all have any recommendations? What do the ladies like on a man’s feet these days?
Leather manacles.
Tsk, tsk. I saw that coming. But don’t you suppose it would be inappropriate to put manacles on feet, seeing as manacle is derived from manus, or hand? Perhaps you meant leather shackles? 
Those too. 
Arden, it goes without saying that you are a naughty, naughty girl. I hope you can make it to the NYC 'fest.
As for the OP: I vote for Docs. Love love love Docs.
Why? Not because they’re good-lookin’. I cannot see why it’s so cool to have the biggest, blackest, clunkiest shoes you can get.
Did somebody declare Bulgaria the coolest place on Earth when I wasn’t around? Or is everybody in on the joke except ole Hushpuppy-wearin’ Bluesman?
Hi, Geobabe!
Aww, Bluesman, you know I adore you beyond all reason, but let’s face it. You’re a big ol’ dork. Docs are cool.
And are you cyber-stalking me again? Thanks! smooch!
Blundstones.
Well, I’ve always preferred some black army jungle boots I got at the army surplus store right before a journey across the Boundary Waters of Minnesota into Canada. I eventually used them as workboots, as the line of work I was in at the time demanded getting my feet a little wet (landscaping).
The ladies don’t seem to mind. The insides have worn out, so I did invest in Dr. Scholl’s, but otherwise they’ve lasted rather well over the years.
Another chick chiming in for Doc Marten’s!
I believe it depends on the situation. I have several sets of Army boots, known for their long-lasting nature and comfortability (a-hem. I have to: I’m Army).
More importantly, I have a set of the 'ol steel-toed Docs and a pair of Carolina motorcycle boots – the kind with the buckle strap over the foot arch. Very cool.
I’d have to say Docs are really worth the money. They may be pricey, but they look good, are comfy and last forever.
Check out Caterpillar’s boots. Them’s some serious footwear.
Frye makes an excellent boot, but for my money, I’d go with the Docs. It’s what I’m wearing, and I think they will outlive me.