Boots: Because nobody looks good in sneakers.

My favorite boots: New Rock #272, Justin #1434, Matterhorn #1997

Dr. Martens, ~1996

The first boots I purchased to live in were 8 hole Dr. Martens, black greasy style. I bought them because I was done wearing sneakers, and these were popular among people I knew. Probably in college (~1996). I don't have anything good to say about them. The leather is thin, the soles wear away too easily, and although the soles are soft, the inside is so hard and flat that they are uncomfortable. They were completely inappropriate for even casually wandering in the woods.
I still have them, they are in bad condition.
Their website is entirely flash so I can't link you to the model.

Classic Timberland

Due to my Docs being inappropriate for the woods, I picked up a pair of Classic Timberlands. They were entirely good for hiking. Unfortunately the plastic(?) support around the heel melted and deformed in the heat of my car, very disappointing.
I still have them, they are uncomfortable due to the heel deformation.

Frye Harness 12R / Engineer Harness, 2000

Then I started getting into more interesting stuff. I purchased a pair of Frye Harness 12Rs, which I was very fond of until they started falling apart on me. Which was particularly disappointing since this is "the oldest continuously operated shoe company in the United States." The inside of the heel completely came apart, and when dry, stabbed me in my heel. Frye was very cooperative about replacing them. But the replacements didn't do any better. The straps fell apart. Again they were cooperative in replacing them, offering to let me pick another model since this one wasn't working out so well. This time I went with their Engineer Harness boots, which actually looked more interesting to me. I'm disappointed with how they held up as well, mostly the toes being crushed so easily - a feature of all the Frye boots I've owned.
I still have the last pair, I don't wear them because they are so broken down.

Cove Shoe Matterhorn #1997 All Weather Combat Boots, ~2001

Then, due to my problems with my previous boots falling apart, I decided to get something practical, rugged. Something that looked nice, but would withstand all that I could put it through. This lead me to ask what the U.S. Marine Corps wore. I ended up buying Matterhorns, model 1997. I'm wearing them as I type this, I've lived in them for 4 years. They make me very happy.
These have a Vibram Sierra sole which is soft in the middle, so they are well cushioned.
They also have a fully gusseted tongue (attached all the way up), so they're waterproof to the top.
They come with 82" laces.
I wear these every day.

Justin Boots style 1434, Black Corona, 10/27/2002

Then I needed some dress shoes. The obvious answer was some nice cowboy boots. Justin's in fact. I'd known of this brand for years as the best. I had done a bit of research, and then one day I stumbled upon a store that happened to have exactly what I wanted in stock. Numerous girlfriends have thought they were silly - until they saw how good they look with a pair of jeans. Or slacks.
Unfortunately these boots are designed for civilized activities. The leather is not very thick. But they look nice, they are shiny, and they feel wonderful, very fitted.
I wear these for all formal occasions.

New Rock model 272, 10/20/2003

Then it became time for something more appropriately unreasonable. I had been thinking about buying New Rocks for a couple years, but never found a store that stocked what I wanted. I finally broke down and ordered them over the internet - overseas in fact. I have enjoyed them immensely, and lived in them for about a year until I started having problems with the crease in the left toe cracking, and bought a motorcycle which I still haven't figured out how to upshift while wearing these boots. They're due to be picked up today, with a new patch across the cracks.
I expect to wear these whenever shifting on my motorcycle isn't a problem.

Cove Shoe Matterhorn #1997 Waterproof All Leather Field Boots, second pair!, 6/29/2006

That's right, my old pair was worn enough that I felt I needed some new boots, and I couldn't find anything that I liked more, so I got another pair of Matterhorn #1997's. There are differences, not surprising since it's been 5 years. The lining has gone from yellow-ish to burgundy-ish. The lace grommets are split on the inside which concerns me (similar to lace-chewing Dr. Martens). But they look and feel great, we'll see.

Future

I'm clearly due for some new boots. Unfortunately nobody makes anything unreasonable enough for me. My Matterhorns at least need to be resoled, and due to imperfect care over 4 years are developing cracks. I'm considering Wesco Combat Boots.
As far as I can tell, Wesco makes the best loved boots, from wilderness firefighters and loggers to boot fetishists. And I'd say fetish quality is better than combat quality.

Maybe I'll get Wesco 18" Harness boots. nchanter thinks they look far too reasonable for me.

I want the look of New Rocks, the fit and durability of Matterhorn combat boots (including fabric lining), and the armor of motorcycle racing boots (Sidi Vertebra, including their replaceable armor).
And probably some more metal.

I ordered Alpinestars Tech 4's with the intention of having them resoled with Vibram 100R heavy lug soles plus an extra half inch of EVA rubber. They turned out to be prohibitively uncomfortable

I want shiny combat boots ("Spit Shineable" according to the Cove Shoe company).

1525: Mens Leather Field Boot
These Corcoran Field Boots look nice, although only the toe cap and counter are shiny.

985: Mens Leather Side Zipper Field Boot with Lug Outsole
The version with zippers is entirely shiny, but I don't want zippers.

978: Mens Leather Plain Toe Combat Boot with Lug Outsole
The plain toe version is entirely shiny, no zippers, and a cleaner looking toe. Mmm, shiny.

XCS2525: Mens Leather Steel Toe Field Boot with DD Comfort Outsole
But with only a shiny toe and counter, I could finally have a steel toe.

Care

It is my experience that any boots, without a fabric lining, worn daily, will fall apart due to the moisture (and salt?) from your feet. For this reason I don't know why anybody makes good boots without a fabric lining.
They all recommend that you alternate between two pair of boots, to give them time to dry between wearing, so maybe its entirely to sell twice as many boots.

My boot care over the years has primarily been:

Wipe them down with a wet cloth to remove dirt.
Dry them.
Slather them with leather lotion (with my bare hands).
Wait for them to dry.
Rub them down with black shoe polish (most recently with bare hands).

I've just rubbed my Matterhorns down with a thorough coating of mink oil to attempt to help with the cracking. At this point it is my opinion that anything worth applying to boots should be applied with bare hands.

I've just ordered some Obenauf's Heavy Duty Leather Preservative to replace the boot care products I've been using. I'm very curious how it will work out.
I am also curious about Montanna Pitch-Blend Leather Dressing. I believe the addition of pitch means it makes leather more waterproof and less breathable.

Repair

People should go to Shoe Repair places more. They do cool stuff with good footwear.
I've heard these two guys in greater Boston are good:

Davis Square Shoe Repair
(617) 776-8580
260 Elm St # 104
Somerville, MA 02144
(map)

Jimmy's Shoe Repair (in Central)
(617) 868-8838
42 Prospect Street
Cambridge, MA
(map)
mon-fri 8am-6pm, sat 9-4

I am ashamed to admit that I do actually own sneakers. I purchased them around 2003 because people told me that gyms wouldn't let me on their treadmills in combat boots. I hated every minute I wore them. I don't know where they are and I don't expect to wear them ever again. What are sneakers good for that combat boots aren't ? How many years have military recruits run in their combat boots ? My Matterhorns came with a sole that's soft in the middle, so they are actually very well cushioned.

If you are not running a race, and you are wearing sneakers, it can only be due to lack of self respect.

I also own sandals, and wholeheartedly approve of bare feet.

On 3/29/07 I bought sneakers at a dedicated running shoe store. They are way more cushioned and springy than my Matterhorns.
"What, don't you respect yourself anymore? ;-P" - Bill Jonas