this reminds me so much of a similar line of inquiry i was having with a really good pal, and i think he gave me the best advice. he told me that i needed to think about what kind of choices would make me feel the most confident and attractive because, "you'd look more attractive to most guys bald, but confident, than any style or change that leaves you feeling insecure and in need of validation. confidence is more attractive than any external option". while that's a pretty broad example, i think the principle is absolutely true for both genders, but even more true for women.
so, in that direction, i have to echo largely what seoulsearch said, which is to let your specifics guide your choices--and perhaps the most important question to ask is how much time and upkeep you are willing to do. some cuts are going to require you to spend time with some of those medieval torture devices to replicate and maintain it. what's the minimum length you need to put it back? how important is that? for me, that's my personal mason-dixon line. however, if you wear a ponytail every single day, maybe you would benefit from an update.
i'm not really going to say too much about what i think you should do because i think this is an issue that you can only answer, but you might want to do some research.
sometimes you just need educated opinions of what decisions will effect what you're hoping for. there are choices that are high and low maintenance and some that will give you a lot of bang for your buck. what's also cool is that they have so many options available as things have advanced so much and continue to do so in that industry.
i'd really encourage you to find a salon that had good stylists that get regular training (ask because good ones do) and when you see someone whose hair you like, approach them, and find out who/where they get their hair done. : ) that's always how i find a good one. most stylists will make an appointment just for you to do consult to talk about what you're hoping to accomplish. they can put their hands in your hair and give you good recommendations, then you make an appointment, so nothing is happening too hastily.
one thing i find a little fascinating is how some women like to keep things as similar as possible and resist change and fight to stay in their comfort zone, but after awhile we almost become blind to the info that we are constantly taking in. of course, some of us are constantly wanting some form of personal migration or reinvention and our hair and makeup becomes the surrogate of all that need for change--but those girls are kind of erasing aspects of their identity by constantly changing things.
i think something in the middle is probably better. i personally like having some aesthetic constants in my life and have things that are somewhat signature for me. actually, i like that a lot. i think you can update without sacrificing what feels like "angie". if you're really interested in some specific suggestions, you know you can always message me.
as long as you're not running around town in pigtails and knee socks, i think you're good. i used to wear pigtails a lot when i'd go work out (for obvious reasons) and one day a guy friend offered me a whole new perspective on that styling choice, effectively ruining it for me. but that's more my issue. ; p
