How do I grow my hair out?

(Without it looking stupid.) Is that pretty much inevitable?

I have no experience with men’s hairstyles as I have only had very short hair since I transitioned. I’ve been buzzing it with a size 1 or 2. But I’d really like to grow it out now and find a low-maintenance style that works for me. I’m not even sure what my hair will look like long now, because the hormones might have changed its texture. But it’s very thick.

I’m mostly concerned about looking unkempt around the ears and sideburns while I’m growing my hair out. Mostly, I don’t want to look like one of the scruffy teenage boys that I teach. Is my best bet to go to a barbershop and ask for a maintenance trim while I’m growing it out? Do guys do that?? I have no experience at all with men’s barbershops in the U.S.

Thanks in advance for any suggestions.