DIY chalkboard wine glasses from the Dollar Store {step by step guide}

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A couple weeks ago, I gave you all a look into a little black dress bridal shower that was thrown for my best friend.  I showed that for the shower game, we had a wine tasting.  It seemed to be very well received by all of the guests!  For me, I had a blast getting the game ready and that included making these really cute {and inexpensive} chalkboard wine glasses.  Not only did they serve purpose during the wine tasting game, but they doubled as party favors for each guest to take home.  As promised earlier, here is my step-by-step guide at how I created them!

DIY Chalkboard Wine Glasses

DIY Chalkboard Wine Glasses | step by step guide on www.theweddingbyjen.com

Step 1 : Buy wine glasses at the Dollar Store

I never realized how expensive wine glasses could be until I wanted to buy more than a set of four or six {I needed about 20 for this party}.  I was just about to give up when I walked into the Dollar Store and right up front was a HUGE display of wine glasses.  I couldn’t believe it.  Not only were they really decent quality, I couldn’t beat the price tag.  This particular store had enough on hand for what I needed, but I do believe you can order in bulk from the Dollar Store if you were looking to get these for your wedding or other large event.

Step 2 : Wash and dry the glasses

DIY Chalkboard Wine Glasses | step-by-step guide on www.theweddingbyjen.com

DIY Chalkboard Wine Glasses | step-by-step guide on www.theweddingbyjen.com

Although the quality of the glasses from the Dollar Store were great, a few of them had obviously been sitting on the shelves for a while.  A quick wash, rinse, and dry were all they needed.  And, to be fair, I would wash any glass that I had purchased {boxed or not} before starting this project, not just because they were sitting on a shelf at the Dollar Store!

Step 3 : Lay down newspaper AND wax paper on your working surface

DIY Chalkboard Wine Glasses | step-by-step guide on www.theweddingbyjen.com

If you have ever painted anything and then set it on newspaper to dry, you know what can happen.  The newspaper dries directly onto the item and you are left trying to peel it off.  The solution I came up with was to set the freshly painted glasses on wax paper.  I kept a layer of newspaper below the wax paper for security…if that paint seeped through the wax paper somehow, I did not want it on my counter tops!

A little side note regarding where you decide to do this project: make sure you have about double the surface area available than what the glasses {when set out} take up.  You will be moving the glasses around while they are drying {more on this below}, so you need to be able to have enough room to move the entire lot of glasses from one spot to another.

Step 4 : Gather the necessary painting supplies

DIY Chalkboard Wine Glasses | step-by-step guide on www.theweddingbyjen.com

DIY Chalkboard Wine Glasses | step-by-step guide on www.theweddingbyjen.com

You will need chalkboard paint, a shallow dish {that is wider than the base of the wine glass}, a small foam brush, and a few sheets of paper towel.

I bought an entire pint of Rustoleum’s Chalkboard paint.  For the 20 glasses that I did, however, I certainly would have only needed to use the smaller can that is available to buy.  Luckily I love crafting and I love using chalkboard paint!

For the shallow dish {that you will be using to dip the wine glasses in}, I recommend using one that has a snap-on cover so that you can just leave the paint in it and store it right in this container when you are done with the project.

The little foam brush is necessary for air bubble prevention and the sheets of paper towel are going to help avoid excess paint pooling on the bottom of the glass.

Step 5 : Dip the wine glasses

DIY Chalkboard Wine Glasses | step-by-step guide on www.theweddingbyjen.com

Dipping the wine glasses into the paint allows you to get a perfect line around the stem of the glasses.  You can dip the glasses as far as you like, but I chose to keep the paint on the bottom of the glasses and {for the most part} off of the stem itself}.  I figured people would be holding onto the stem and I wasn’t sure how the heat from their hands would mix with the paint.  I didn’t want to risk everyone getting black chalkboard fingers!

After you dip the wine glass, hold it over the container for a few seconds, up to one minute, to let the excess paint drip off.  I would tilt the glass to the side after a few seconds to really get the excess paint off.

This step is also where the foam brush may begin to come in handy.  If you get an air bubble in the paint, very gently poke it with the corner edge of the paint brush.  Do this only when the paint is still really wet so that it can still smooth itself out from where the air bubble popped.  If you try to pop the air bubble once the paint has dried a bit, you will be left with some jaggedness from the air bubble popping and the texture from the foam brush {it isn’t pretty and there is no way to fix it, trust me on this one}.

Step 6 : Remove some of the excess paint from the bottom of the glass

DIY Chalkboard Wine Glasses | step-by-step guide on www.theweddingbyjen.com

DIY Chalkboard Wine Glasses | step-by-step guide on www.theweddingbyjen.com

DIY Chalkboard Wine Glasses | step-by-step guide on www.theweddingbyjen.com

Immediately after dipping and after letting some of the paint drip back into the container, run the bottom of the glass along a sheet of paper towel.  This step is key!  It removes a good majority of the paint from the bottom of the glass and will help prevent a HUGE mess once you set the glass on the wax paper.  You just need to swipe each glass once and I was able to swipe two glasses per sheet of paper towel.

Step 7 : Set the glasses on the wax paper to begin drying

DIY Chalkboard Wine Glasses | step-by-step guide on www.theweddingbyjen.com

DIY Chalkboard Wine Glasses | step-by-step guide on www.theweddingbyjen.com

The wax paper is the perfect solution so that you do not end up peeling paper off the drying paint.  However, the paint is not going to soak into the wax paper.  This is why swiping the excess paint off the bottom in the previous step is beneficial.  The reason being is that the excess paint that is still on the glass {you are never going to get it ALL off before setting it on the wax paper} is going to start to pool around the edge and bottom.

Step 8 : Begin the rotation process

DIY Chalkboard Wine Glasses | step-by-step guide on www.theweddingbyjen.com

DIY Chalkboard Wine Glasses | step-by-step guide on www.theweddingbyjen.com

The pooling of the excess paint does present you with one possible issue if you were to just leave the glasses sit in the same spot.  That pooled paint will eventually dry.  I guess you could probably chip it off the edges of all the glasses after the paint dried, but I found it easier {and more clean looking in the end result} to just move them around.  I laid down another area of wax paper covered newspaper and moved the glasses to this new, fresh wax paper after about 15 minutes of initial drying.

I would then just keep going back and forth between these two areas.  I would remove and discard the first area of wax paper, lay a fresh sheet down, and rotate the glasses around every 15 to 30 minutes.  I moved them back and forth about five times…basically until the last time I went to move them, I didn’t see any more paint pooling around the edges.

It might also be noteworthy to point out that I was using “durable” wax paper.  This would not be the time to skimp…this wax paper saved my counters!

DIY Chalkboard Wine Glasses | step-by-step guide on www.theweddingbyjen.com

DIY Chalkboard Wine Glasses | step-by-step guide on www.theweddingbyjen.com

Step 9 : Turn the glasses over to dry the bottoms

DIY Chalkboard Wine Glasses | step-by-step guide on www.theweddingbyjen.com

DIY Chalkboard Wine Glasses | step-by-step guide on www.theweddingbyjen.com

After the tops of the glasses seemed dry {I gave it about three hours before I did this step}, I turned the glasses over so that the paint that was still left on the bottoms could dry.

Step 10 : Write on the glasses!

DIY Chalkboard Wine Glasses | step-by-step guide on www.theweddingbyjen.com | Photography by Kat Shanahan Photography

DIY Chalkboard Wine Glasses | step-by-step guide on www.theweddingbyjen.com | Photography by Kat Shanahan Photography

DIY Chalkboard Wine Glasses | step-by-step guide on www.theweddingbyjen.com | Photography by Kat Shanahan Photography

DIY Chalkboard Wine Glasses | step-by-step guide on www.theweddingbyjen.com | Photography by Kat Shanahan Photography

DIY Chalkboard Wine Glasses | step-by-step guide on www.theweddingbyjen.com | Photography by Kat Shanahan Photography

DIY Chalkboard Wine Glasses | step-by-step guide on www.theweddingbyjen.com | Photography by Kat Shanahan Photography

DIY Chalkboard Wine Glasses | step-by-step guide on www.theweddingbyjen.com | Photography by Kat Shanahan Photography

At the party, I set out a Bistro Chalkboard Marker that I got on Amazon {affiliate link} and everyone wrote their names on a glass so that we could all keep track of which glass belonged to each person.

And that is it!  A pretty simple DIY project that results in a super cute wine glass for you and your guests.

I have one more post in mind that relates to this bridal shower and wine tasting game – stay tuned for a closer look at the wine tasting game itself with free printables to use at your own party!

Also, thank you so much again to Kat Shanahan Photography for the beautiful pictures from the party!  If you are in the Madison, Milwaukee, or Fort Atkinson areas and are in need of a wedding or engagement photographer, please consider Kat {I do believe she travels and has photographed weddings in Appleton and Green Bay , as well, for all of my Fox Valley readers}.  Along with her website, you can also find Kat Shanahan Photography on Facebook.

For more DIY wedding related projects, visit The Wedding by Jen’s DIY archive and make sure to follow me on Pinterest for lots of additional unique and modern wedding inspiration finds!

If you tackle this project for your wedding, post a picture on my Facebook page, I would love to see it!

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42 Comments on DIY chalkboard wine glasses from the Dollar Store {step by step guide}

  1. Mari
    September 14, 2014 at 11:34 am (2 years ago)

    Love the idea. Chalk paint has become my new friend:)

    Reply
  2. Emily
    September 15, 2014 at 7:57 am (2 years ago)

    WOW!!! that is SO clever… I love this idea… pinning! Chalkbaord paint is so amazing.

    Reply
    • invitesbyjen
      September 15, 2014 at 8:50 am (2 years ago)

      I am still experimenting with chalkboard spray paint (I wish it went on things a little more thick), but I put chalkboard paint on anything I can get my hands on!

      Reply
  3. Stephanie Pass
    September 15, 2014 at 9:47 am (2 years ago)

    Oh I love this! I think it’s so much better than those little beaded things to figure out which glass is yours. Such a cute idea!!

    Reply
    • invitesbyjen
      September 15, 2014 at 10:36 am (2 years ago)

      Yes! My thoughts are that after a couple glasses of wine, are you really going to remember which beaded thing was yours?

      Reply
  4. Deanna Ritz
    September 15, 2014 at 10:57 am (2 years ago)

    Your glasses turned out really cute! You did a fantastic job! I’m going to have to make these for our next party. Thanks for the idea. 🙂

    Reply
    • invitesbyjen
      September 15, 2014 at 11:11 am (2 years ago)

      Thanks, Deanna! They are super easy to make, just make sure to have enough counter space to move them all around!

      Reply
  5. Margaret
    September 15, 2014 at 1:01 pm (2 years ago)

    Very cute! I haven’t played with chalkboard paint yet, but my list of projects keeps growing. Now I have another to add to the list. Thanks for sharing.

    Reply
  6. Katie
    September 15, 2014 at 3:51 pm (2 years ago)

    Such a cute project, they turned out great! I need to get a chalk marker!

    Reply
    • invitesbyjen
      September 16, 2014 at 8:40 am (2 years ago)

      I love having the chalk marker, so much cleaner in the writing!

      Reply
  7. Melanie
    September 15, 2014 at 5:06 pm (2 years ago)

    I love anything that can be upcycled from the Dollar Store!

    Reply
    • invitesbyjen
      September 16, 2014 at 8:40 am (2 years ago)

      Love Dollar Store crafting!

      Reply
  8. Debi @ Life Currents
    September 15, 2014 at 5:25 pm (2 years ago)

    Really cute! I love all the awesome ideas for chalkboard paint.

    Reply
    • invitesbyjen
      September 16, 2014 at 8:39 am (2 years ago)

      Chalkboard paint and the Dollar Store are two things I like to hear in the same sentence, for sure!

      Reply
    • invitesbyjen
      September 16, 2014 at 8:38 am (2 years ago)

      Yes, I promise they are so very easy!

      Reply
  9. Candace
    September 15, 2014 at 8:36 pm (2 years ago)

    SO cute so creative – I love them!

    Reply
  10. Camila
    September 15, 2014 at 9:22 pm (2 years ago)

    WOW what an awesome idea!!!!!! It just makes me want to get married again!!! ….
    XOXO

    Reply
    • invitesbyjen
      September 16, 2014 at 8:38 am (2 years ago)

      You could make these to celebrate your anniversary 🙂

      Reply
  11. Jillian
    September 16, 2014 at 2:46 am (2 years ago)

    Such a fun DIY project, and it looks easy to do.

    Reply
    • invitesbyjen
      September 16, 2014 at 8:37 am (2 years ago)

      Yes, it is super easy!

      Reply
  12. Britni
    September 16, 2014 at 11:04 am (2 years ago)

    This is such a fantastic idea, love it!

    Reply
  13. Limeade Gal
    September 16, 2014 at 2:08 pm (2 years ago)

    So darn cute! Love your step by step with all the tips 🙂
    Would be fun to do for all kinds of celebrations, thanks for sharing.

    Reply
  14. Barb
    September 16, 2014 at 2:19 pm (2 years ago)

    How fun!! Looks easy enough.

    Reply
  15. Maggie @ The Love Nerds
    September 16, 2014 at 3:35 pm (2 years ago)

    Chalkboard and Wine Glasses? Of course I am saying yes! These turned out fabulous.

    Reply
  16. Krystal's Kitsch
    September 18, 2014 at 11:14 am (2 years ago)

    I’ve always wanted to make these. They are so cute!

    Reply
    • invitesbyjen
      September 20, 2014 at 7:32 am (2 years ago)

      Yes, definitely give this project a try!

      Reply
  17. Sergio
    October 1, 2014 at 6:04 pm (2 years ago)

    I just found your blog and love this idea! What size did you make your book tags, so that there was enough room for the kids to write on them? Thanks!! 🙂

    Reply
  18. Kevin
    October 1, 2014 at 8:10 pm (2 years ago)

    Thanks for these thoughts. I’m in a hotel room in England, wntiiag for a wedding tomorrow and it’s probably more nerve-wracking for me than the bride or groom! I am a Christian + have had SA for 15yrs and with God’s help am working with it + getting through it. Just some days (like tomorrow) are a bit scary. Thanks for the inspiration. I’ll think if that when I’m talking to strangers tomorrow. God bless.

    Reply
  19. Amy
    March 27, 2015 at 6:30 am (2 years ago)

    Hi there, these are adorable. I am going to make some to sell at a fundraiser for my Relay for Life team and wanted to ask how they stood up after some time? I don’t want to sell something that they can only use once and the paint scratches off? Can you let me know?
    Thanks! 🙂

    Reply
    • invitesbyjen
      March 28, 2015 at 8:56 am (2 years ago)

      These will need to be hand washed. The paint will not hold up to a cycle in the dishwasher. Good luck with your fundraiser!

      Reply

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