
1.

2.

3.

4.

5.

6.

7.

8.

9.

10.

11.

12.

13.

14.

15.

16.

17.

18.

19.

20.

You're so much better than Cambria.
What this font says about you: "I am strong, assertive, and cry without fail whenever I watch Titanic."
By Micah Rich.
What this font says about you: "I like a nice Merlot, but I LOVE a nice strawberry André."
(Check out The League of Moveable Type for even more incredible open-source fonts.)
By Tyler Finck.
What this font says about you: "Yeah, I saw the value in The Great Gatsby, but I vastly prefer Fitzgerald's lesser-known work."
What this font says about you: "I know I have two master's degrees but my fantasy is to shuck my old identity and open an old-timey saloon out West."
(Lost Type is an awesome co-op that operates on a pay-what-you-want model, as do many of the other sites on this list [so even though you CAN get their stuff for $0, chip in some cash when you can — it's how groups like this get to keep putting out innovative stuff]. And rules for whether you can use a font for commercial as opposed to personal use vary, so double-check that as well.)
What this font says about you: "Life's too short for 2D or serifs."
By Jason Mark Jones.
What this font says about you: "I have a secret Pinterest account entirely devoted to outdoor weddings but I'm not even positive I want to get married."
What this font says about you: "The next person who asks me to design a T-shirt for their charity 5K is getting an email filled with porn spam."
By Dominic Le-Hair.
What this font says about you: "I will give you the best hug of your LIFE SO FAR."
By Jorge Artola.
What this font says about you: "I look super sweet on the outside but if you cross me I swear I will bring you to your goddamn knees."
What this font says about you: "I am the most whimsical of them all!"
By Steve Cloutier.
What this font says about you: "NO I AM, YOU POSER BITCH."
(DaFont is another fantastic resource for free and pay-what-you-will fonts.)
By Peax Webdesign.
What this font says about you: "I own Prismacolors."
By Peax Webdesign.
What this font says about you: "I once ate my coworker's pad thai out of the office fridge but usually I'm a pretty upstanding person."
By Julia Petretta.
What this font says about you: "Sometimes I stay out until 7 the next morning and I haven't paid for my own drinks since 2009."
(Font Squirrel is a veritable font* of wonderful free collections as well.
*font joke.)
By Typografski.
What this font says about you: "I've grudgingly entered the 21st century but you'll have to hold a gun to my head before I so much as look at an Instawhatever."
By Tension Type.
What this font says about you: "Between you and me, my eggs Benedict recipe is way better than this brunch place's."
By Pablo Impallari.
What this font says about you: "I have at least one tattoo inspired by a children's book. No, you can't see it."
By Vernon Adams.
What this font says about you: "I know how good I look. You don't need to tell me."
By Jonathan Hill.
What this font says about you: "EVERYTHING I SAY IS THE MOST IMPORTANT THING. Ugh, sorry, sometimes I have a moment. Carry on."
What this font says about you: You are me.