it is the custom during the month of high holidays, from the new year until the celebration of the giving of the torah (bible), that the challot be rounded, as in the circle of life, and sweeter than usual — served with honey (or sugar) instead of the traditional salt for hamotzi (sanctification prayer).
so, here are two round shape "how-to's" that are can be used for the month of tishrei — one traditional and the other a little different (and sephardi), in the shape of a flower/rose. we called it el flor (the flower). other round shapes to be added later (hopefully) .....
classic turban shaped ("round")
high holiday challah
perhaps the easiest challah there is to shape, this is the traditional shape for rosh hashanah and all the holidays following it until simchat torah.
take a piece of dough and shape it into a strand which is slightly tapered at one end, sort of like the shape of a baseball bat. the length will depend on how much dough you are using and the size of the challah you want.
grab hold of the thicker end, and start to wrap the strand around the central part.
wrap it until you get almost to the end.
tuck the end of the dough underneath. make sure it is secure.
the finished challah. add your eggwash and sesame/poppy seeds.
a (sephardi) variation of the typical turban style loaf (above), i know this as the rose or flower. it was sometimes called the sultan's hat (chapéo del sultán) because of the shape (1 . 2. 3) as you can see from the picture below.
make a strand which is as long as your arm from the top of your shoulder to the tip of your hands. i usually make it longer. it should be about 1 1/2 to 2 inches thick. this is important as it gets doubled.
match the tips and double the strand. now twist it tightly and press the two ends together.
lay the twisted rope flat and hold the looped end. pull it up a bit (straight up) and coil the doubled strand around this central part. remember to start in the same direction you twisted or you'll unravel it!
tuck the end in underneath . make sure it is secure.
voilà. let prove and then coat with eggwash and sesame or poppy seeds.