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I used wrap around labels on my STD's. I found the template on martha stewart. They looked great I thought!
Printing addresses on envelopes is actually really easy. I did that for the envelopes for my invitations and RSVP cards. They looked really nice! The most annoying part is just setting up the text in Word or whatever so that it prints right on the envelope. Once you get it right, it's just a matter of printing it 100 times lol.
That said, I think labels are also fine.
@deathbydesign: I second your entire post. Labels are fine, printing on envelopes isn't as hard as it sounds.
I hope not! We're planning to use clear labels on shimmer silver envelopes because the metallic finish doesn't absorb ink well. I hadn't thought of printing directly onto the envelopes, though....hmm.
Hmmm, OK, maybe we will go with the printing on the envelopes!!! Thanks everyone! This is going to be my weekend project. 
I think it is fine. Noone but us brides on here notice labels, trust me. :) Type it, print it, stick it, send it, DONE!! haha.
I printed directly on the envelopes. Like deathbydesign said, the tedious part is setting up the addresses in Word. But that actually worked out because I can give that Word list to my MOH so she knows all the addresses and guest names. She can use that list to send out bridal shower invites and record who gave what gift so I can do my thank you notes.
ETA: Having said that though, I still think it's perfectly fine to use labels for your STDs.
My wedding planner says that STD's can be more casual so I think printed labels would be just fine.
I was going to use labels for mine, but the clear label didn't look good on my dark red evnelopes. So I decided to hand address them. Yeah, I WISH the labels would have looked good because I SOOO would have preferred to do that!
I printed on my envelopes, it worked fine...
It works best to do a mail merge if you have your guest list and addresses on a spreadsheet, then you can set up the addresses how you want, do a quick once over of every envelope and then print them out... It didn't take long at all!
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Our STDs are cards so I am wondering if it tacky to print out the addresses on clear labels? I hope to get a calligrapher for the invitations, but it's too much $$ for the STDs. And I hate my handwriting.
Thoughts?
DF Suggested printing the addresses right on the envelopes but I feel like that would take forever and be a pain in the butt.