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. Justins 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.
About 2010 I wore through the tip of the toe on one.

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.

1/25/2010 Wow, almost another 4 years. The only thing I can really complain about is the paint wearing off a grommit.

Ariat Sedona Oiled Black, 11/5/2007

I was looking for something more durable than my Justins. They're nice, but still not as sturdy as I'd like.
Size 10.5 D.
I'm still actively wearing these in 2019, very fond of them.

Danner Fort Lewis, uninsulated, April 2012

I'd found raving about Danners, specifically Acadia and Recon, and the Fort Lewis appears to be a 2" taller version of the Recon. And uninsulated because I think I'm probably better off varying my socks. It does have cambrelle (fabric) lining for durability, which seems to be the good stuff. Other than that I expect them to be basically the same as the Matterhorn #1997's, but a little better quality. I wish they were available with non-squishy soles, maybe I'll get them re-soled with Vibram 100R's. I got them a half sizer larger to more comfortably fit thick (REI ragg) wool socks. I'm happy with the squishy soles. I hate the lace D-rings that rattle. I much prefer the hook style speed laces.
Freaking expensive.
I'm still actively wearing these in 2019.

Future

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.

Other

I'm interested in Wesco Combat Boots and wesco harness

Wesco 18" Harness boots. But they cost over $400, damn.

It would be fun to get the look of New Rocks, the fit and durability of the best combat boots (including cambrelle lining), and the armor of motorcycle racing boots (Sidi Vertebra, including their replaceable armor). And some extra 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

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 (most recently 2020-01-29):

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

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

Ah yes, I can be an opinionated thing. I haven't lived in boots for years. I live in Merrell Moab Ventilators. Low top. They're incredibly comfy, well ventilated, and these days I'm less concerned about always wearing shoes that are optimized for the collapse of civilization.
*shrug*