When i transitioned the styling was actually easy...i just looked a hot mess (no really, lol).
I would wash and condition my hair (Con and whatever random conditioner i could get my hands on). Then i would roller set, sit under my hood dryer, put coconut oil on my new growth and relaxed hair and smooth it into a wrap or comb it straight back, and throw a scarf on overnight.
At the end of the transition i didnt have the patience or inclination to rollerset it so i would shampoo and condition, douse it in coconut oil...coax it into a wrap (wet wrap) or just comb it back and tie it down with a scarf overnight and use a curling iron to bump the ends.
I wouldn't recommend you go my route if you still want to look cute tho, lol. I never flat ironed or put any direct heat on my new growth bc i did not want to damage it...i didnt care about the relaxed hair so i would hot curl it like everyday, sleep w/out scarves on sometimes...i also cut my hair to chin length so that the relaxed length could be somewhat presentable.
Coconut oil really helped though. Id just slather it on my new growth and tie it down and it would lay flat. If you want to look silky smooth all the time though you'd probably need to flat iron your roots. I don't recommend it though.
Good luck!
Would u consider transitioning in braid extensions?