How to Monogram a Pocket on a “Boyfriend” Shirt

Remember the preppy Oxford shirt from the 80’s?  It’s making a comeback and it looks great monogrammed.  This makes me so happy since I love monogram, and I LOVE, LOVE, LOVE the 80’s. (I’ve been working on my big hair for about 9 months now so I hope it comes back too. I’ve just been letting it grow and wearing it curly. I have natural curl in my hair.)

The Oxford is making its way back to fashion.  I have been seeing it referred to as being a “boyfriend” shirt.  I see it with the collars buttoned and unbuttoned like this one from Old Navy.  It looks great oversized with a pair of leggings or jeans AND of course adorned with a set of initials. 

They are really popular with brides and their attendance to wear as they get ready for the wedding. The brides are usually giving them as gifts.  A few brides even put the wedding date and “Bride/I Do”  on the cuffs.    A big oversized button-up shirt is great for not messing up the hair or make-up. (Notice that this one below does not have a pocket.)


I have even monogrammed a shirt for a friend’s daughter for prom (seen above in the first picture).   And instead of handing down my son’s Oxford to my nephew, I monogrammed it for my daughter to wear with her leggings (seen below).  She is nine.  Her first reaction was “I’m not wearing that boy shirt!”  She changed her mind once she had the hot pink initials on it and especially after she was complimented on it in the grocery store. 


I have had great success with adhering the pocket shut prior to adding the monogram.  I use Heat n Bond Lite to close the pocket.  Heat n Bond Lite (HNBL) is double-sided iron-on adhesive.  It can be purchased at any fabric store, Walmart, or even Amazon. 

Materials needed:

Heat n Bond Lite

Medium Cut away stabilizer

Spray adhesive (if using fast frame)

Tear away stabilizer (optional)

Given: iron, thread and machine


I cut a piece slightly smaller than the pocket. 

I slide it into the pocket making sure it is flat in the entire pocket.  I slide it in with the rough side of the HNBL facing down and the paper side facing up. 

I iron the pocket.  I may need to pass the iron over the pocket several times before the HNBL sticks.  Follow the directions on the HNBL for iron temps as well as the suggested heat setting for your shirt fabric.  Steam is not needed for HNBL.

Once the shirt is cool to the touch, I peel the paper backing from the HNBL.  I work my hand towards the bottom of the pocket as I peel it away. 

Then I slip the paper out.


I pass the iron over the pocket again to adhere the pocket to the now exposed HNBL.  This closes the pocket.  I like the stability that the HNBL gives the pocket.  Not only does it give a little stability to the pocket, it keeps the puckering around the monogram to a minimum.  Oxford and other men’s dress shirts are usually made of thin fabrics, and no matter what stabilizer  is used, the weight of the thread/monogram is heavy and usually causes some gathering/puckering around the curves of the monogram.  I have found that closing the pocket helps with this as well as keeps the pocket looking nice wash after wash. 

 Now the is pocket is ready to be hooped or in my case attached to my fast frame. I use a medium cut away stabilizer and spray adhesive to attach the shirt to the fast frame.  Sometimes I float a piece of cut way under it all.  I am sure I over stabilize.

 With this shirt of mine, I used tone on tone for my color choice. 



 Wondering about the cuffs???  I simply pinned them to a piece of tear away that I had attached to my fast frame.  They are one of the easiest things I have ever embroidered.  

 If you have any  questions, please feel free to comment. 

Follow Me on Pinterest

13 thoughts on “How to Monogram a Pocket on a “Boyfriend” Shirt

  1. Jan says:

    I’m new at monogramming and names. Can you recommend fonts that sew out well, just to get me started? I found some on Etsy but have not tried them yet. I also use to get some. I have PE-Design. Thanks for any tips to help me get started. I have a friend who wants me to embroider a name on a towel. I have no idea which font to use. I have gotten pretty good at appliqué.
    I was born in Biloxi, but my family is from Texas. My cousin, a contractor, moved to New Orleans a few years ago to help with reconstructions after Katrina.

    • ramiparker says:

      Hi Jan

      Thanks for reading my blog and welcome to the addicting world of embroidery. I get a lot of my fonts for names and monograms from a site called They stitch out beautifully. Most finished products you see on my site are from there.
      I use PE Design Next but I’m thinking they work the same. You will need to import your letters from your saved file individually.

      I am thinking that dafonts allows you to digitize true type fonts in your pe design program. While these give you a wide variety of fonts they don’t digitize the satin stitch quite like a font that has been digitized by a professional digitizer. Where they will go back and forth around all the curves, using a true type font via the pe program doesn’t quite do that. It may digitize long wide stitches that look very awkward.

      I hope this helps some.

    • ramiparker says:

      It really is true that we are all about 6 degrees from separation. I love the MS gulf coast….maybe even more than New Orleans.

  2. Faina says:

    Is there a way to do monogramming while leaving the pocket functioning, like on a men’s dress shirt? Do I need a commercial machine for this purpose? What machine do you use? Thanks.

    • ramiparker says:

      Hi Faina,
      Thanks for reading and asking your question. I have a Brother PR650E. It is a six needle machine and would be considered a commercial model. A lot of businesses use them as well as do folks for personal use. Even with my machine, I could not embroider the pocket so the pocket would still function as a pocket. The pocket would have to be large enough for the so called neck of the machine to fit inside the pocket leaving enough room for the top of the pocket to move around for monogramming. To embroider the pocket and still have it function, people remove the pocket carefully from the shirt, monogram it, and then sew it back in place.

      Hope that helped. Thanks again for reading and always feel free to ask questions.

  3. Chris Henson says:

    Do you recommend a certain font to add just a tiny monogram to my husband’s pocket on dress shirts?? They all seem to stitch out poorly when that small. Thanks!

    • ramiparker says:

      I know what you’re talking about with small fonts. Some programs have a small font specifically for this. Let me know if you have that option. I’ve never used that option on mine but I’m willing to program your husbands initials for you to give it a test run. Let me know.

  4. Beverly says:

    This is so helpful. I just got an embroidery machine and am learning. My niece is getting married and asked me to monogram 10 shirts. I told her the only way I knew to do it was for the pockets to be sewn shut after the monogram was done. She ended up ordering some off of Etsy.

    • ramiparker says:

      I’m sorry she didn’t get you to do them. It’s not like a female ever uses a pocket. I’ve been at this for years and find that I’m still learning too. I think it’s a process that allows for continued growth. Not to mention with so many technology means of networking, others are always sharing tips and tricks.

Comments are closed.