I practice Iaido and your question got my attention. Are you talking about Iaido obi? I am a girl but I am fairly big and my obi feels comfortable when proper tied, please refer to the links: http://www.kimono-taizen.com/wear/w_kaku2.htm http://www.kimono-taizen.com/wear/w_kaku1.htm
But some of my friends have a very small waist and they prefer to wrap some towels below the gui, which creates a more square shape and avoid the problem you mentioned.
I personally have 3 things to consider about Iaido obi:
1. I hold my breath to tie it a little tighter before making the bow. Once you start the bow you won't be able to make it tighter
2. Iaido and everything relate lies in a delicate balance. The obi should never be too tight or too loose.
3. talk to your Senpais about how to proper tie your hakama himo. The himo is tied different in different styles and it will influence your experience in batto
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