I have always worn my hair super short. usually a mixed cut pixie, high over the ears. then covid. stayed home and now its been 3.5 yrs since I've had a 'real' cut.
I just shaved my neck and otherwise let it go until it was long enough in the back to pull into my 'RBG' low pony, wore headbands to hold tops/sides to my head.
as it grew, I started trimming only the longest hair in the back while the rest was left to grow. literally turned my head upside down, combed all hair forward so I could cut the very back (and see what I was doing).
now days, I keep trimming the longest while the straggling shorter hairs keep growing. I can wear my hair in my tinkerbell top knot and am thrilled with the look.
first time in my life to have long hair. actually FAR easier upkeep than pixie that needed daily wash, products, hair dryer, etc.
all else fails, wear a hat ;-) good luck :-))