In all historic clothing (pre-1870) the buttonholes are hand-stitched, and many after that have hand-worked buttonholes. Sometimes they were worked using an overcast stitch, other times a button-hole stitch. Overcast buttonholes tend to be stiffer and are good for rarely-used areas. Button-hole stitch buttonholes (say that 3 times fast) are great for much used areas of a garment, they are flexible & last a long time. They use less thread than overcast holes and lay flatter.
Occasionally in modern clothing you will find that your machine won't make the necessary stitches. Either the fabric is too thick, slick or delicate... or your machine is out-of-wack & needs to be tuned up by a professional.
And sometimes you just want that beautifully tailored look that hand-sewn buttonholes give a garment.
Here is a simple method of making hand-sewn buttonholes (by no means the only way). It's on wool, using 3 strands of cotton embroidery thread for the finish.
Sorry about the dark colors, I've included line drawings next to them in case you can't see the photos on your screen. The photos are better than the drawings...
Click on the pictures for a larger view.
1. Mark the location of your buttonholes with tailor's chalk, or some other removable fabric marker.
Alternatively, you can use pins or tailor's tacks (those little knotted threads that you put through the fabric).
Make sure all of your buttonholes are marked evenly & consistently. (Three separate buttonholes are featured in this tutorial, the one at the collar is lower than the cuff holes).
2. Back-stitch around the buttonhole* using very small stitches. The buttonhole should be narrow-ish, but no narrower than 1/16" or you won't have room to slit between the fibers and may end up cutting fabric that you don't want to.
This holds the fabric layers together & reinforces the sides of the buttonhole. It also gives you a guide for your hand-stitching.
*You can create some really interesting buttonhole shapes at this stage.
3. Slit the buttonhole** with a razor or seam ripper.
**You may want to fray-check before you do this.
Start from one side & go to the center.
Start from the other side & go to the center to complete the slit.
Doing it this way prevents the "oh sugar!" of slitting through your fabric.
4. Sew the buttonhole.
Secure your buttonhole thread from the back.
(no picture: bring the thread in from the side. Let the needle & thread come out between the layers of the buttonhole until the end of the thread is lost in the fabric. Insert your needle in the edge of the buttonhole again & loop the thread around it twice. Pull tight... gently... and tighten the knot with your thumbnail. The thread should be at the edge of the buttonhole. You may now start your buttonhole from the front of the garment.)
All work is done on the top side of the garment.
Starting from the open slit, pass your needle 1/2 way through the fabric to the outer edge of the back-stitching line. Stop.
Loop the thread over the needle once (like passing a car on the right in the USA, or passing legally in the UK) or twice (for an 18th c. buttonhole stitch).
See picture above (by #4).
Pull the thread tight, making sure your "knot" ends up right on the edge of the buttonhole.
Start the next stitch the same way.
The "knots" should be almost invisible when you are done.
-Make any corner stitches close together & keep your length-wise stitches even.
-Make sure all of your stitches are on the outside of the back-stitch line.
Continue until the buttonhole is competed.
You may want to provide some extra reinforcement on the end where the stress is (the outside edge) by making a few more stitches.
You can continue with the buttonhole stitch or use a tack stitch for the end of the buttonhole.
Tie off your thread the same way you attached it... wrap the thread around the needle twice. Pull the knot tight & pass the thread under the stitching on the back side, (you can go all the way around the buttonhole, but it's not necessary). Lose the end in the fabric & cut.
The back of the buttonhole is pictured here. You may be able to see where I "lost" the thread between stitches.
The really wonderful thing about hand-sewn buttonholes, aside from looking great is that you can do so many interesting things with them... without buying expensive cams for your sewing machine.
Most buttonholes (1" long) take about 10 minutes to complete.
Make buttonholes 1/4" larger than large buttons, 1/8" larger than small buttons. Check the fit after the first hole, or make a test version out of similar fabric before marking up your garment.
If you've never done this before, start on a test swatch, or some out-of-the-way place on your garment... don't make your first buttonhole at the front neckline of your bridal gown...
If you have any questions, or need clarification please leave a comment. I'm on cold meds, so the directions may not be as clear as I think they are.