Very Long Post that gets updated once every couple of years. Information may not be fully up to date, but will be a reasonable indicator of what I was using over the years.
I am on Photoshop CS6. 

Brushes you should get:

• Kyle Webster sets Megapack, Concept, Gouache (if you don’t have updated Photoshop, ask someone who does to save out the ABR files for you)
• This one brush https://jyangart.gumroad.com/l/defaultbrush
  

I always use brushes at 100% opacity; it helps your marks to look intentional. I occasionally lower the opacity of a layer, but not the brush.

[2022] 99% of my lines are done with that brush on gumroad.

The softer tones—you’ll see I like to add a little bit of orange-red around the fingers/cheeks—are done with a gouache brush (Kyle’s megapack or gouache set). 

Welcome to Kyle Webster Brushes!

[May 2020] I used this brush all the time. It’s also good to experiment with random brushes every so often because I wasn’t using this brush before mid 2019! Kyle’s Paintbox: Gouache Bonus Gritty Dry. If you’re able to zoom in, the lines have a bit more grit than other pieces.

A deeper dive under the cut! + body horror + SUPER long post warning

This is the same gouache brush, but applied solely to linework. It’s slightly less ink-like than the on-gumroad brush. 

Pencils—my favorite pencil brush is KYLE Ultimate 2B Pencil 10px. It’s the lineart for the piece below. If the gif loads for you, you’ll see I often block out the shape of something before filling the insides with colors (with clipping masks). Fills are done with the lasso tool, the first Google Drive brush, or Kyle’s Inkbox: Low Ink Fat Flex. (The gif is also on the front page of my website if this post doesn’t work)

Kyle’s Inkbox Rough Inker 3 is good for this sort of thing where you pray you’ve got the right color combinations and smack them all down at 100% opacity. Dogs here are Rough Inker 3, plus a multiply layer set at a lower opacity (probably 30%), and a radial gradient over it all to make them stand out. 

Honorable mentions for Kyle brushes I’ve used in the past: Kyle’s Paintbrush: Big Bad Wolf 175 Tilt, Palette Knife 3, and I highly recommend you all try out the concept brushes to see if you like any of their textures!

[Out of date; haven’t kept up with where his brushes went; may not be available online]

Let’s talk about Alex Negrea’s Brushes.

They’re good for specific things! They’re all labeled in nonintuitive ways, so I find it helps for me to put my brush view on Stroke Thumbnail in three columns. A & B are at the top when you have them like this, and C is a slight scroll down on the first column. 

Uses for A (Aufgenommener Pinsel 4 5—do you see what I mean about the names now). Great shape for some texture.

The steam/clouds in the far right of below is also a good example of its texture:

B (Sampled Brush #7 7) for the swishy textures in the background! The other more rock-like texture is one of the mountain ones from Kyle’s Concept Brushes. 

Brush C is mentioned bc it’s a cool brush but not personally applicable to me! 

Two not-brush-related tips while we’re at it

• When doing a portrait, it’s much more interesting if the hands are doing something, i.e. fiddling with an earring, holding a pen, clenched together in worry; go to museums and just look at hands (© Tim O’Brien’s advice ahaha) 
• The most important piece is the next piece, not the current one. (might also be © Tim but I’m not sure, I love that guy he’s the art dad)

….and we’re done! Hope y’all have fun experimenting!

Feel free to leave a tip at my ko-fi link