I've gotten a couple of requests for an updated milkmaid braids tutorial with my shorter hair, so here you go. I'll probably try to shoot a video of it sometime, but hopefully the photo format is also helpful.
First off: you don't need long hair for milkmaid braids. Approximately shoulder length and with a few shorter layers will work--like my hair. If your hair is slightly shorter or you have more layers then try styling your hair when it is damp.
Start by dividing your hair into two parts and then braid each section. You want to braid your hair tightly at an angle pulling it towards your face/the front of your head. My braids typically go over my ears and sort of stick out at a angle.
Once both sides are braided, use some bobby pins to pin them to the top of your head. I put bobby pins in from the back of the head towards the front. It usually takes me around five bobby pins to get everything to stay in place. If you hair is longer you can tuck the unbraided ends under the braids, but if it's slightly too short for that (like my hair) just bobby pin the ends together.
That's it--you're set! If it feels unsteady then you can use some hairspray to secure it all in place. But as you can see it's still pretty simple even if your hair isn't Rapunzel length. To me this a very functional hairstyle; I like wearing it on hot or windy days when I don't want to deal with my hair getting in my face or super tangly, so I think it works even if your braids aren't the smoothest or longest. It's about convenience rather than elegance.