I've recently gotten into bootblacking and I find it really enjoyable! Getting to do the boots while the person is wearing them generally leads to a surprising and pleasurable energy exchange.
Your basic kit doesn't have to be very fancy:
* a couple of horsehair daubers (round)
* a couple of horsehair brushes (rectangular)
* saddle soap or glycerin soap
* leather conditioner (4-Way, Cadillac, Huberd's, Obenauf's)
* cream polish or wax polish
* shine cloth or old cotton t-shirt
* spray bottle with water
* low-lint towels (t-shirt cloths, sold in packs in the paint dept. at Home Depot, are commonly used)
My favorite polish is Kelly's, but that has little to do with performance and mostly because I love the flowery/jasmine smell. Meltonian, Angelus, Lincoln, Kiwi, and others are also popular. Really, main thing is that you want cream or wax polish and should avoid those liquid polishes with the sponge applicator bottles. Also, you'll want one rectangular horsehair brush per color of polish in your kit. You want to avoid using a brush with dark polish on lighter leather.
Notes on cream vs. wax: Cream polish will give only a light shine and is best for garments and any other items on which you desire a more matte polish. Wax polish is what you want if you're trying for a nice, bright shine on boots and shoes.
If you start to do research, you'll see that everyone has their own way, so it can get a bit confusing. The first thing is determining whether you have a polishable ('high shine') boot or whether it's oil tan leather. This is probably the hardest thing in bootblacking, because it takes a little experience with feel and the appearance of the leather to determine quickly. I read somewhere that if you put a drop of water on the boot, let it sit for 30 seconds, and wipe it off, if the leather is darker where the water was, you're dealing with oil tan. Some types of boots, like harness boots and cowboy boots, are generally oil tan, but not always.
Most high shine boots will have a smooth finish and appear glossy, although sometimes, there is too much dirt to tell. However, finished leathers aren't always hard like on high shine boots; with a softer coating, the leather will feel softer and supple. Because the leather is coated, usually with resin, it will feel cool to the touch when under your hand.
Oil tanned boots generally have a pitted look to them, a bit of a nap when you feel the leather, and are either dull or medium shiny (low luster). This type of leather will warm easily under your hand and is often described as 'buttery soft'.
I know this is very confusing when you start out, so rest easy in the knowledge that every working bootblack has accidentally polished oil tan boots at least once. The good news is that it's not harmful to the leather and is simply a sort of embarrassing novice fuck-up, so if you do polish oil tans, don't fret! Just apologize, clean the polish off, and condition.
Step 1, remove laces and set aside. If doing on someone's feet, roll up their pant legs and try to remember how they like their boots laced because you'll have to do them up again at the end.
For oil tan boots:
Get a dauber wet and mist all over the boot with the spray bottle, as well as the surface of the saddle soap. Rub the brush in the soap, then apply it to the misted surface in small circles. You're going for a nice, satisfying lather... not too much water, but not so little that it's not soaping up. You don't want the saddle soap to dry on the boot, so if you're quick, you can do the whole boot at once, but if the leather is really dry, you'll have to work in sections because the soap will dry super fast. Spritz a clean t-shirt cloth until damp and wipe soap off thoroughly. Get all up in the crevices, the tongue, straps, etc. If a boot is really dirty, I'll repeat this process. Having a small bowl of water is helpful to rinse your brush once it gets dirty, as is a cheap toothbrush to clean the catwalks and other details. When you finish one boot, set it aside to dry a little and start on the other.
Starting on the first boot, work in your conditioner, gently massage it in if you can. If you like the person, make it a foot and ankle massage through the leather. Pay extra attention to the creases because it'll help maintain flexibility where the leather gets stressed. You don't really want to use tons, necessarily. Sometimes, leather is thirsty and may take a lot of conditioner, but overall, you're aiming to leave no excess on the surface. Huberd's can take a bit to fully soak in, depending on how dry the leather was. I would condition the first boot, set aside to soak in a bit, do the second boot, and then use my grease brush (used only for conditioner) to buff off the excess. You could likely use a lint-free cloth like a t-shirt to buff off the conditioner. Too much conditioner can actually weaken fibers. Also, keep in mind, if you have non-black leather, some conditioning products might darken the leather leather a bit.
For polishable boots:
Same beginning steps as oil tan boots, but I've been cautioned against using Huberd's before applying polish. Some experienced bootblacks do it, but the idea is that Huberd's is oilier than the other products and polish won't adhere as well. I'm a baby bootblack still, so I haven't much personal experience in this matter, but a very experienced bootblack busted out some science to explain it and I'm convinced. So, basically, you can use anything but Huberd's if you're planning on applying polish. Obenauf's is maybe a bit pricey, but it's natural, soaks in quickly, and can be polished over.
Once you've cleaned and conditioned the leather (don't forget to buff), apply polish to the boot in an even coat. You can use a dauber for this, a smooth damp cloth, or your bare fingers. Get it in all the cracks, creases, etc., and be careful about getting dark polish on non-black stitching. If you do get polish on light stitching, a cosmetic (pointed) q-tip dipped in rubbing alcohol generally helps a lot. Or you can sort of cheat and get yourself white and yellow China markers, which is what the veteran bootblacks all stock in their kits to brighten up stitching. Depending on the design of the boots and the color of the laces, you may or may not want to polish the tongue, as polish will wear off against the laces. Do this on the first boot, set it aside for the polish to dry a little, repeat on #2.
Lightly mist your polish brush -- barely damp, not wet -- and starting with the first boot, lightly brush the boot in quick, repetitive strokes over one area, then change angle and do the same vigorous brushing motion while going across the same area (like an X). I find I need to do this longer than I think I do, but I suspect that I might be using more polish than necessary.
What this does is knock off extra polish, but it also is building up heat via friction to melt the polish a little and make it smooth. Keep the brush barely damp and repeat until you're satisfied. Set the boot aside and do #2.
With the first boot, take out your buffing cloth. I have a shine cloth with a soft side and a hard side, but some people use t-shirt cloths, which I've heard works just fine as long as it is laid flat with no creases. I buff lightly with the soft side, then I flip the cloth over and buff lightly with the rougher side.
To get a better shine on high-shine boots, people tend to use nylons. A little pressure is required in this step. If someone is wearing the boots I'm doing, I'll flatten the nylons like a cloth (no creases) and do the classic shoeshine back-and-forth thing on the toes and heels. You can put your hand into a leg of the nylons and it makes it much easier to rub the sides, or if you're trying to polish empty boots. You're aiming for friction and you know it's good and polished when it starts to squeak.
You can repeat the polish step as many times as you like, or even just do extra on the heel and toe.. additional layers will increase shine to make the toes and heels stand out against the rest of the shine. I personally don't do the nylon step with every pair of boots because I've found that it's best on high shine boots, and can actually reduce shine on other finishes.