I have an older HP P1006 laser printer (black-and-white), which I use exclusively to print envelopes.  

I bought a newer HP 1606 laser printer (black-and-white), which doesn't print envelopes worth a darn.  It tends to wrinkle and destroy envelopes. The reason I bought this printer is because it prints regular paper on front-and-back, something my P1006 does not do.

I had an older Epson Workforce 630 color inkjet printer.  It printed envelopes okay.  It had only one tray, so I had to pull out the paper tray, take out the older paper, put in envelopes, and print.  But it printed envelopes okay. 

I replaced the Epson 630 with a Epson WF4720.  I don't think it prints envelopes as well as the Epson 630 did. And that is not saying much.

I say all this to say that I find not all printers will print envelopes with the same quality work.  You will have to find what works best with your printer.

The other thing I find is that laser printers do not handle window envelopes very well. I use window envelopes for billing, and the heat of the laser printer just destroys the plastic window.  So, I use window envelopes in my inkjet printer, or use a regular envelope in my laser printer. 

I hope this helps.  If you have more questions, post them.