I’m a lady and I don’t think there’s anything wrong with what you are feeling, for a couple reasons. First, I think a lot of people’s appearances are symbolic of them holding onto the past. Not to draw too much from pop culture, but if anyone watches What Not to Wear or any other makeover-type show, you see these women who are still wearing their frumpy maternity clothes four years after giving birth because they can’t move on and accept their post-baby body. Or you see the women who cut off their hair that’s down to their back and they’re bawling the whole time because it’s so emotional to change such a big part of them. So first, I would ask if there’s anything from the past that your lady might be holding onto with her outdated look. Maybe there’s a deeper meaning that she needs to work out.
Secondly, when you see people on those makeover shows, the spouse usually says something like, “She was gorgeous before, but now she looks so great and so happy.” It’s not that you don’t love her the way she is, but you see that she could be reaching her full potential, and she’s not with an outdated hairstyle. I think for a lot of people the fear of change keeps them from trying anything new.
In term of suggestions….First, praise her incessantly if she does try a new hairstyle that you like (without being so obvious that you are trying to encourage it). Definitely try to talk to her lady friends and see if they could suggest something nonchalantly. Or, get her a spa package as a gift with the whole works—massage, manicure, pedicure, as much as you can afford, and maybe try to either encourage her to “treat herself” to a cut or tell the stylist to suggest it. I think part of the reason why those makeover shows work is because when it’s coming from a professional, it’s professional advice. When it’s coming from a husband, it’s “He doesn’t love me and thinks I’m ugly and wants me to change.”
Now, beware because this could backfire if she happens to ask the stylist if you put her up to the suggestion, but I think trying to get a professional to suggest it rather than you would be the best. If you’ve mentioned this to her in the past, it might be a sore subject already. The more you push her, the less interested she’ll be in trying something new.
An ex of mine was balding and I never, ever suggested the “buzzed look” even though I knew it would make him look way younger and sexier. He wore his hair the way he wanted it, and I went along with it, never saying anything to him. I think he was also more than a little bummed to be losing his hair and didn’t want to accept that. It wasn’t until his barber took ill and his hair got so long that he finally asked me to buzz it off. The compliments he got on it afterwards quickly changed his mind about his hairstyle and he’s kept it very short ever since. Sometimes you just have to let people figure this stuff out on their own.