Simulated commercial envelopes and methods of making are disclosed. An example envelope includes a first envelope portion having a front panel. A top flap is integrally formed with a top edge of the front panel about a first fold line, and a bottom flap is integrally formed with a bottom edge-of the front panel about a second fold line. A second envelope portion includes a rear panel free of any fold lines or flaps. The rear panel is to be secured to the front panel to form a pocket at least partially surrounding the mailer. The bottom flap is to be folded about the second fold line and to be secured to the rear panel on a side opposite the formed pocket. The top flap is to be folded about the first fold line and to be secured over the rear panel on the side opposite the formed pocket.