To confront my rude friend?

[addictedtolove022]

I have a friend who is much older than me. We met at work and just gelled. We have been close friends for about 6 years now.
I mention her age because she is of that generation where they don’t mince their words. However…I went over on Monday to do her a favour, take her to an appointment. When I arrived she told me she didn’t like my outfit.
I didn’t say anything at the time but found myself justifying what I was wearing (for context it was just leggings and a matching top as I had been out walking the dog and running errands). Later on I thought this isn’t the first time she’s commented on my appearance. It bothered me a lot. I just don’t see the need in saying something which is going to bring someone down? Especially a friend who is doing you a favour?
I text her that evening and told her she had made me feel quite down and I didn’t appreciate her commenting on my appearance. I’m sure I don’t always “like” what my friends are wearing but I don’t feel the need to point it out as it is only going to bring them down? They’re entitled to wear whatever they like.
But now I find myself myself feeling bad for saying something to her. She did apologise but made out I was being over sensitive and she was just making a joke? Which I don’t agree with at all.
So AIBU??

My mum is of a certain generation (born in the 1940s?) and a lot of the time it's too difficult to get her to say what she thinks, she will hint at best then ends up being put upon or unhappy, reacting in a passive aggressive way or silently furious that other people haven't been considerate of the needs she hasn't expressed. It's not out of a desire to be difficult, like many women her age she was raised to put everyone else first (especially her husband and children), "be polite" and not assert herself or advocate what she needs.

On the other hand I know as a friend of friends (we're sort of in the same group but I would never call her a friend) someone who is pretty much the same age as my mum. She emulates the super polite, solicitous, always thinking of the needs of others behaviour my mum was brought up to but she regularly uses it to dress up snide remarks, insults and comments that jab at people's weakest and most sensitive points. Think faux concern like "Are you sure this is the right relationship for you, he's probably going to leave you for someone more in his class" to a friend who was dating someone with a higher status/more middle class profession than their own. I've seen her do this to several very kind, decent people who would have called her a friend and she doesn't show the slightest remorse if they express hurt. I'm pretty sure she enjoys hurting people and causing drama.

Your "friend" sounds much more like my friend of friends than my mum.

I'd say she's got a hide like a rhino. Sometimes you need to check people and that's fine.

Familiarity breeds contempt… her commenting on your looks is an example. And you casually making assumptions about a whole generation.

Absolutely this

I’m going off my own experiences of people of that generation.