
It’s so fun to get holiday cards into the mail each year, but the envelope addressing part might make you want to skip it altogether.
Crooked lines of text, addresses that won’t fit, and smeared ink are enough to make a person want to hand deliver the envelopes instead, or even print the addresses!
This may be true, but nothing beats handwritten text. My heart skips a beat when I see my best friend’s handwriting or my sister-in-law’s handwriting emerge from my mailbox. Check out my article, “Stop Comparing Your Handwriting to Calligraphy”, for more on this nuance. Read on for my top tips for envelope addressing, no matter the paper, pen, or address!
Envelope Addressing 101
Just in case you need a refresher, here’s what to include when addressing an envelope:

The recipient’s address in the middle of the front of the envelope:
- Addressee’s name
- Street Address
- City, State, Zip Code
- or, for international addresses, city, province, country, postal code
You should also include a return address just in case the postal service can’t deliver your letter. The return address goes in the top left corner on the front of the envelope and includes:
- Your name
- Street address
- City, State, Zip Code
The postage stamp goes in the top righthand corner of the envelope. Write the main address on the front of the envelope far enough from the top that there’s adequate space for the stamp to fit and be “cancelled”. This means that the Post Office will place an ink-stamp over the stamp, defacing it so it can’t be reused later.
Tip #1: have extra envelopes Available
This might not be what you expected to be the first tip. Accept that we all make mistakes and it’s better to prepare for them that to assume they won’t happen. Knowing that you have a couple extras takes the pressure off and makes the writing a little better.
In addition to this, you’ll need an envelope to test your ink, pen, or marker on. Make sure the ink doesn’t feather or bleed through the whole envelope. After it’s dry, try to smear the ink by rubbing it. If it stays in place, you’re good to go!

How many extra envelopes? About 20%, or one-fifth, more than the number of addresses you have. For example, I’m sending about 35 cards in the mail this year. 35 divided by 5 is 7, so the 35 envelopes plus 7 extra means I’ll need at least 42.
I haven’t bought envelopes in awhile, but I like the ones from PaperSource and Cards and Pockets (not affiliate links).
Tip #2: Use guidelines
If you’re experienced and confident with writing well on a page with no lines, you can skip this tip. I use guidelines to save myself some envelopes though.
There are a couple ways you can do this. If you have a light pad, you can make a template with guidelines on it and place it inside the envelope. Switch on your light pad and you can see the lines to write on without having to draw them. I use this method for light-colored envelopes. I test how well I can see the lines through an envelope by placing an envelope over a piece of paper with something printed on it. Then, I hold both pages against a window in daylight.

The alternative? Drawing the lines. I do this for dark or opaque envelopes. I still make a template, but I extend the lines beyond the edge of the envelope. Then, I use a ruler and lightly draw the lines in. Dark envelopes are a commitment for envelope addressing, but they’re soooo pretty.
Tip #3: Keep it Legible
Take care with your envelope addressing to make sure your card gets all the way to the person you’re sending it to. If your handwriting is hard to read, my best tip is to write very slowly. This will help you focus on the basics. You can also try writing in all capital letters, again, very slowly.

As a calligrapher, I avoid complex and over-flourished cursive on envelopes. I would hate for an envelope to be returned to sender and delayed because it wasn’t legible, both for my clients and for you.
Here’s an example of a returned envelope I sent out in 2020 during an artist’s exchange. I got it back a couple of months after I sent it, who knows the adventures it had! So glad I put the return address on there, otherwise I never would have known it didn’t make it to the artist. I actually think the address provided was incorrect, but this is a good example of what an envelope can go through from point A to point B!
Bonus Tips
Centering Envelope Addresses
Here are a couple of tips that help me to center addresses. For more in-depth tips on centering text, read my article, “3 Tips for Centering Text“.
- Start further to the left than you think you should
- Write the name and address on a separate piece of paper first to see how much space you need
Centering the ZIP Code

I learned from Suzanne Cunningham to center the zip code by writing the 1st and 5th number, then the 3rd number centered between them. Then, center the second and 4th numbers.
For example: 85719
I’d write the 8 and the 9. Then, I’d center the 7 between them. Lastly, I’d add the 5 and the 1.
Protecting Your Envelope

If you love to add stickers, jewels, raised calligraphy, or any collage to your envelope, you can still send it through the post. Enclose it in a clear, sealed bag. BUT you’ll still need to put the postage on the outside layer of the plastic so the post office can cancel it properly.
If you’re going to send a set of envelopes and you’re not sure they’ll make it to their addressees without being returned, swing by the post office or visit USPS.com for more details about how much postage you’ll need to add.

Need Cards to Send?
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Thank you.
Absolutely! Hope it helped!