First off, you'll never believe me, but you are definitely hotter in your thirties than your twenties so give it a minute, or a decade, it's gonna be OK. Secondly, this letter could get really long real fast, so I'm not gonna give you all my epic middle-thirties wisdom at once, nonetheless, prepare yourself.
Save yourself a TON of headspace, time, and emotional energy by choosing not to give a rats hiney about what people think of you. Now listen, I'm not talking about the "drunk frat girl with a butterfly lower back tattoo, and the personal motto 'Only God Judge Me'" kind of carefreeness, AKA foolishness + rebellion in their most potent form. I'm talking about choosing to spend your intelligence, thought processes and emotional life on things that matter, rather than wondering if So and So is pissed cuz you told her you think designer handbags are a waste of money before you noticed her Prada wallet. Or changing your outfit 5 times because people might think it's too "colorful, boring, revealing, frumpy" etc. Girl, life is FAR too short to spend it trying to please everyone or caring about what they think of you at the expense of your identity. People think about other people MUCH less than they think they do, because they are far too busy thinking about themselves. Take back your brain, and enjoy the clutter free zone of enjoying who you are without wondering if everyone approves.
Secondly, try not to get caught up in the comparison/competition wars that seem to plague young women. As a teen, you thought the whole thing was bizarre and baffling and you should maintain that position as you grow older. Because comparison, as we are told, simply steals your joy. You were created to be you for a reason; looking at someone's differences with anything more than curiosity and appreciation (like envy, for instance) is the fastest path to dissatisfaction and bitterness. As for competition, a hard fact of life is that someone may be competing with you without your knowledge or consent. If you become aware of it, don't enter this imaginary competition. Just like drag racing is a risky endeavor, female competition is dangerous. It ends friendships, causes untold problems, and breeds monstrous insecurity. If you suspect a close friend is trying to compete with you, confront it. If it's not a close friend, realize that person is not someone you want to get close to. They are not your friend, and they have more problems than you want to deal with.
Let me say one more thing about competition. Don't doubt yourself. If you have a nagging suspicion someone is not "for" you, don't talk down to yourself and talk yourself out of your intuition. You may be someone's biggest fan while they are simultaneously competing with you in some invisible popularity contest. You aren't wrong, and you aren't stupid. Ignoring all those small but hurtful things without standing up for yourself isn't doing anyone any favors. It will all come out eventually and your attempts at pretending it doesn't exist will be in vain. A mark of maturity is realizing you are valuable too!
Lastly, you will deal with a heartache you never expected. I'm not talking about guys here. I'm talking about other women. People who you thought were your friends were using you to feel better about themselves. Women that you believed had your back were secretly sabotaging you. Friends you cared deeply for didn't care for you when you really needed them. Your "squad" may dwindle as you get older, and the people in your corner may become fewer. But mark my words, those few will be rich, deep friendships that have aged well like fine wine and are as strong and soul soothing as a cup of coffee. Hang out with the friends that have been there for you, maintain closeness with those who value you, and work hard to keep in touch with friends who nourish you. Friendships are an invaluable part of life that come easy with youth and are more difficult to maintain with age. They are worth it. As are you.
Your Older, Slightly Wiser Self
PS - Don't cut your hair. You'll regret it BIG time. Also, stay away from all guys not named Christopher.