How To: Tailor a Button-Down Shirt for a Perfect Fit

created at: 2010/02/11

Men’s shirts are sized in crazy ways – sometimes its sleeve length and neck dimensions, sometimes they’re in chest dimesions (like a suit), and often, just the unpredictable small-medium-large. So, men, too, often have to buy for certain body measurements – length, sleeve, neck sizes, chest girth – and have other aspects not fit. It’s why most men’s button down shirts are baggy with big sleeves, and that weird muffin-top thing that billows out when we tuck them in.

So, next time you find that perfect vintage buttondown at the second hand shop, but it’s flows around you like you’re swimming in a gingham plaid Superman cape, pay the .99, take it home, and grab your sewing machine.


  • A baggy button down shirt – this works best with shirts that fit around the shoulders and chest, but are too big around the sleeves and sides/length
  • Mirror
  • Pins
  • Sewing machine and thread
  • Scissors

1).  Stand in front of the mirror, and/or get a friend to help you. Put on the shirt inside out, and button it from the inside.

2). This method is called the pinch and pin – so do just that. Begin with the sleeves and pinch the fabric until it’s tight around your arm, but you still have full range of motion. Pin it from the cuffs to the arm pit.

3). Then do the same thing around your torso. Since most men’s shirts do not have seams in the back, pull the excess towards the side seams, and pin from the arm pits to the waist.

4). Then, just sew a single stitch from the cuffs through the armpits, then down the sides. Sew just outside the pins, so that it doesn’t get too tight and restrict movement.

created at: 2010/02/11

5). Flip it inside out, and throw it on. Done and done.