When I went through beauty college, I had a different color hair on a regular basis. I changed styles, cuts, and length too. It's hair. Grow it out, change it up.
While in my older age, I've sort of stuck with styles that I prefer, all that went out the window the first time I got chemo, and all my hair fell out. That's a shocking sight. At first, I used head coverings. (I found wigs to be hot, itchy, and the scalp is very tender.) At home, after family and friends got over the initial shock of seeing me bald, I stopped wearing head covers at home. I only wore them when going out in public.
After chemo, when the hair started growing back in, it does not grow in evenly, so I still had to clipper cut it close to the scalp for a bit. Once it had all started growing in all over the head at a more even rate, I stopped cutting it. It didn't take long, and I stopped with the head coverings all together. Yes, the hair looked more like a man's clipper cut, but at that point I had hair. Makeup, earrings, etc. kept me from looking too mannish. Hair does not grow out evenly, so at certain intervals it had to be shaped.
This sort of bomb-proofed my family and friends regarding seeing me with different hairstyles, and radical changes. Dh says I look good to him with both long, and short hair, so he has no preference. It's whatever I want to do with it.
When going radically different, give it time. Everyone will get used to it in time. Hey, I have to admit, when I'd go from one hair color to another, when I'd first change it, it would even catch me by surprise sometimes. I'd be going to the bathroom, and catch a glimpse of myself in the mirror with the new hair color, and take pause.