There is absolutely no way to definitively answer this question.
It's true that the ASC rules a lot about the way you look.....and the Sun rules a lot about who you are authentically....so the square can mean that your looks can give false clues about who you ''are'' if the people you meet judge you or categorize you according to the way you look. Which by the way is common.
And this has nothing to do with being attractive or not. This square can mean that when you look in the mirror there is a disconnect with the way you ''feel'' you should look. If the Moon doesn't aspect the ASC well this also could add to this sense of not identifying with the way you look.
However: there are SO many ways this can be modified.
I have this aspect. My Sun squares my ASC. Mid Leo Sun, Mid Scorpio Asc. In my case, my Venus AND Jupiter are conjunct in mid Cancer and trine my ASC. So technically I know I have a sort of attractiveness that is real....even tho I don't ''feel'' that I am projecting my Sun.
This situation is in a way, fortunate.....because when anything crosses my ASC it does square my Sun, true....but at the same time it is trining my Jupiter and Venus.
This modifies the square.
So you need to figure out if something either modifies either your ASC or your Sun. This will lessen the pressure of the square. Find the modifiers.
LIN
Thanks! I have Venus in Aries in aspect to ASC (Sag) and also Mars in Acquarius also in aspect to ASC (trine and sextile, respectively...).
Jupiter in Taurus sq Mars also, by the way...Jupiter (ruler of Pisces and Sag, lets say) is the only singleton (planet in earth sign) within my chart.
Regarding the Sun-Moon sq; there is Saturn in Leo (trine Moon) sq Uranus in Scorpio (trine Mercury in Pisces); Saturn-Uranus sq seemingly is square Vertex in Taurus.
One of the things that seems to perplex me, so to speak is that of Sun sq ASC plus Sun sq Moon (though Moon is not conjunct ASC: 16° Sag; vs 23° Sag, resp.).
Perhaps both squares relate to a sort of (rather involuntary, not just somewhat unnoticed) "masked" way of life (being); within which things (not the most trivial ones...lets say...either good or bad) seem to come out of the blue from time to time
Greetings