I love type and calligraphy. I’ve been downloading free fonts like it’s my job, and have recently started addressing wedding invitation envelopes. Lots of them. Since any attempts I’ve made at calligraphy have been pretty sub-par (since you probably have to have nicer handwriting to begin with), I’ve had to cheat a little.
There are lots of great calligraphy how-to’s out there, but cheating for me meant something a bit different. Instead of trying to really do it myself, I went online and searched for some free fonts that I could use to create a similar calligraphy effect. And sometimes, finding truly free fonts that you actually like, is hard work! However, I did find some great fonts, several of which I ended up using to address wedding and RSVP envelopes.
I used my silhouette cameo and a pen attachment to use it as a plotter, but you could also print on envelopes with an ink jet or laser printer.
Voila! Check back later in the week for my top free calligraphy fonts with links!
freshwater-studio.com 
Thanks for the insight! It looks like your letters were not filled in… Did you then go over it with a marker and use this as guidelines or did you leave them like this?
Hi Ashley! For this project I didn’t fill the letters in. I thought they looked nice with the negative space. I did practice filling some in though. To do that I just used a fine tip sharpie pen to color between the lines. The letters looked nice both ways but I had so many envelopes to print it would have taken me forever to finish them all!
What kind of pen did you use to write on the envelopes using silhouette cameo?
Hi Sara. I used a black uniball ball point pen. I found the simplest pen worked best (so pens without the special hand grips fit into the pen holder attachment best). Also it had to be a pen with a cap, not a clicky-pen (as I call them).
Gorgeous! What font did you use?