With all of the Procreate letterers out there, you might start to think that the only way to make really great letters is with an iPad. While I'll agree that working digitally has its benefits, I don't necessarily think it's the best (and it's certainly not the only) way to go. The best lettering artists/typographers I know work almost entirely on physical media - paper, windows, glass, walls, what-have-you - and totally slay.
So now you want to know how YOU can make your non-digital lettering as epic as freaking possible, and I'm going to tell you ALL. THE. THINGS.
First and most importantly: PRACTICE, dammit.
I've been lettering since before anyone called it hand lettering or thought it was a fun hobby. Parties 5 or 6 years ago were always a blast.
Them: "So, Kiki, what do you do?"
Me: "I make hand-drawn typography."
Them: “What’s that?
Me: “I draw fancy letters.”
*blank stares, crickets chirping*
(By the way, this still happens sometimes. Just the other day I had to explain to someone what hand lettering was, and at the end of the conversation they’d decided it was the same thing as calligraphy and I was too tired to care anymore.)
The point is, I've been doing this for a long time. These days at least most people know what hand lettering is. In the meantime, I've had the chance to try all kinds of pencils, paints, markers, gel pens, inks, papers, typefaces, techniques, artistic styles, desks, chairs, lamps, and anything else you can think of. All this trying (and all the fucking up that inevitably comes with it) has taught me a LOT.
Now, you don't have to put in as many years as I have to get pretty good at lettering, but the point is that you DO have to put in the hours. You have to train your hands, build up calluses, get blisters on your calluses (seriously, it's a thing), try things, spill ink, cry, scream, and dance in your desk chair while you work. You will not get better just by visualizing awesomeness (surprise!). Get used to the idea.
Buy the best supplies you can afford.
That doesn't always mean the most expensive - there are plenty of good art supplies that are real bargains and are just as good as (if not better than) expensive brands. You don’t have to spend a fortune on art supplies to start drawing - and you definitely don't have to buy all the fancy brands everyone else is talking about. Wanna know a secret? A lot of those popular brands are all hype.
So what should you have in your pencil case?
A few .5mm mechanical pencils with various grades of lead; they don’t need to be expensive pencils, since the lead is what counts most. The only requirement is that you can draw comfortably with them. 2H, B, and 2B is a good selection of lead to start with (I HIGHLY recommend Pentel Ain Stein leads - they are hands down the strongest I’ve ever used, and you get 40 leads for the same price that other brands charge for 10 or 12. Pure magic).
Various erasers, including a large one and an eraser pencil (Koh-I-Noor is my favorite eraser pencil).
A triangular protractor and a compass.
Some black fineliners (and maybe a black brush pen for filling large areas; try to stick with the same brand/type as your fineliners). Pigma Micron and Faber Castell Pitt Artist pens are a couple of good ranges that include brush pens.
A white gel pen for corrections. I prefer Uniball Signo over Gelly Roll - far better coverage and smoother ink flow.
Optional - some metallic gel pens for making things fancy. I personally find that Uniball Signos are the best in this category as well.
You'll go far with those basics. If you'd like recommendations on specific tools or would like some tips on markers or color inks, drop me a line any time at firstname.lastname@example.org. I don't get paid to endorse any brands - I just know what works well.
Now, on to the actual doing.
Ditch that cute little A5 notebook you've been doodling in and don't touch anything smaller than A4 ever again. It's easy to shrink down large drawings and retain lovely detail and crisp lines, but it's impossible to blow up small ones and keep them looking nice. It's also impossible to fit as much detail onto small paper, and every little wobble or rough line is amplified by about a billion times in a small sketchbook. When you work on A4 or A3 and take a snapshot to post to Instagram, all those tiny imperfections (which are a part of anything handmade) are smoothed out nicely when you shrink it down to a little square on a pocket-sized screen, or scan your work and make a greeting card from it.
Take your time. Sketch properly before inking. Draw guides for your baseline, x-height, cap height, slant, etc and stick to them. If your letters are meant to be a consistent size and weight (and they are), make them consistent. Don't be lazy and then say "Oh, that's part of its charm! It's got character!" because we both know you want to make it look as amazing as possible, right? Be precise. It can either look hand drawn, or look totally professional with just a little extra effort.
Use a damned ruler.
Your ruler is the single greatest tool at your disposal - I'm not kidding. Use it to draw all those guidelines I just mentioned. Then, when you're inking, bring that bad boy in first to draw any horizontal lines. All the straight bits that are on the same level get done in one go without moving your ruler (hard to explain, so here's a picture). That makes sure you get insanely precise-looking letters that will be the envy of Instagram.