By high self esteem I mean directly in regards to looks, and to the point of bragging etc; not just being comfortable and happy with yourself.

ur stupid

Mere can you swim? I just thought of the best whale watching scam in existence.

Yes I can...

I bet I've thought of a better one...
Although mine ends in me and Hayden Petite making love on a Japanese Boat.

it's irritating when anyone gets gloat-y about themselves, they're just not fun to be around.

It has been well documented that the most insecure women are the hottest ones.

8 9 and 10s are far more insecure(low self esteem) than a 1 2 3 4s who are generally the most secure women (high self esteem).
I am uncertain as to why this is, but this has been documented by every community, even one's outside the MRA/Feminist camps, for example, a tertiary neutral camp called the PUA(Pick up artist) community has an extensive amount of articles describing this phenomenon.

Shrug.
Fat pride?
Uggo pride?

NOTE:
This absolutely positively does not extend to men.

I find it more annoying when an attractive person does nothing but complain about their appearance.

Ugly people, you can just say "***** u fat" and they think you're joking.

Is this thread about someone in particular?

I think often when ugly people gloat about how attractive they are, it is a form of overcompensating. They know that they are not attractive, so they talk about how attractive they are in order to convince others that it is true.