I will tell you 6 easy steps to create monograms using your cricut machine.

Step 1: Download Free Monogram Font

You can download free monogram fonts from dafont.com. I used font Monogram-kk

Be sure cricut design space is not open and running when downloading font or it will not be add to your font book.

Step 2: Design Your Monogram

Open cricut design space and create our monogram. Select Monogram-kk and enter each initial individually. After getting it the size you want be sure to "weld" your letters together.

The order for monograms are first name initial, last name initial, and middle name initial if all letters are different sizes.
The order is first, middle, last name initial if all initials are the same size.

Step 3: Begin Cutting

Adjust your cricut machine settings to the Iron-on. The cut only goes through the iron-on film and leaves the liner intact. Load gripmat into the machine and cut images.

Turn "mirror" on in design space before you begin cutting

Step 4: Weld Design

Remove negative (extra) Cricut Iron-on film, leaving only the desired cut image on the linear. Using the weeding tool found in the Cricut Tool Kit can make this process faster and easier.

Using the weeding tool found in the Cricut Tool Kit can make this process faster and easier.

Step 5: Apply Design to Shirt

Preheat the area of the material in which you will be applying your cut image by placing heat press on top for 10-15 seconds before adding image. Place the weeded image, liner side up, onto the preheated material. Apply medium pressure with the iron for 25-30 seconds.

Preheating shirt helps removes any wrinkles so image can lay flat.
If using an EasyPress, refer to this Cricut Heat Guide for time, temperature, and peel temperature recommendations depending on your base material and pressing surface.