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I don't usually darken the door of S&B...so explain slowly and carefully...
I think I need glasses...if I get glasses then this will change the way I look. I also want to get rid of a lot of my hair which currently lives in a non-descript ponytail. So should I get glasses then try and work out what hair style might work with them...or get my hair sorted and chose glasses that match the hair?
Hiya.specs wearer of 20 years here to say hair then glasses. I have a moon face and find half updos work well with more delicate specs. Check out glasses direct once you've got your prescription. I'll never buy from a high St optician again.
You cannot grow your hair back from short to long! Hair is the first. Go to the hairdressers with make up on. Look your best. Decide on a style that will uit your face shape. Ditto with the glasses. Don't go for ultra fashionable that you will be sick of in a year. DH just bought his Persol frames from Italy and the local optician put in the lenses. Saved £200. Frames were only £100 from Italy. (He has complex lenses).
My haircuts over 2 year cost way more than my glasses!!! Who has one hair cut in two years?! I guess I must be high maintenance. If you are peering out of long unkempt curtains and then decide to go for a bob with a fringe that is a radically different look. Or maybe a short spiky look. Totally different. The new hairstyle needs maintenance and no-one should go 2 years without a haircut.
All depends on how radical a change of hair you're talking about. Personally it would take me more than a year to go from short to long hair (not that I do) and I would want to continue to have some sort of cut done regularly during that time to give it some shape.
Honestly, please don't be so hard on yourself. I am no oil paintig but a decent regular haircut from someone who knows what they are doing really helps. Colour now too as I refuse to be grey. I know it can be the "thing" on MN to scrimp and save on yourself and spend no money, but it really does make you feel better if you look as good as possible. We are a bit longfaced in my family and my sister has a bob tapered at the back and a fringe. Look at some pictures in hairdressing magazines to get some ideas. They often group pictures by face shape.
Glasses do make a huge difference to your face, of course. You do not need to spend loads, but a good optician will be able to help you choose for your face shape and hair. They will be the new "you" so you need to spend wisely. Don't scrimp on your hair. I am not sure wider glasses are the answer. They can look odd if they are wider than your face. Sometimes deeper, slightly oval ones are better than narrow rectangular ones though. Remember: you are NOT stupid looking!!!
Hair first. Hairstyle and colour can make a big difference to the way glasses look. A hairstyle will grow out if you don't like it, but you'll be stuck with the glasses if you choose them and then find they don't go with your new hairstyle.