First, I don't really believe I'm pretty in any conventional sense (and this is not a plea for "yes, you are"). But I do seem to fall within a subset of society's norm for women. I present as white, cis, hetero, fit, and female; in reality I'm a bit of a mutt, bi, polyamorous, disabled (albeit in decent shape) and female. But I dress on the feminine end of the spectrum, so even with the purple mohawk and a cane I must be "asking for it".
But through most of my college and grad years I dressed in baggy shorts/pants and oversized t-shirts with the same mohawk (in an ever changing array of colors). It didn't stop the harassment on the street or unwanted advances, nor did it do anything to weed out the asshats or deter the men capable of date rape. I'm not that attractive that I understand how I was lucky enough to get attention when I looked like a skater boi, especially since even now I'm a C-cup at best. I outgrew the skate-punk style when I figured out it didn't make a difference, and skirts are more comfortable to wear.
These days I don't get as much in the way of street harassment, mainly because I rarely leave the house, especially alone (go go Transient Global Amnesia). I still get catcalls, honks, stares, rude comments and people trying to touch me without permission when I am out (usually with my male partner), even if it's just at the grocery store or the laundromat and I'm wearing a long skirt and a t-shirt or a baggy comfy dress covered by my cassock/coat. It's not OK.
On the other hand, I also get things like you can't possibly be disabled or sick; you look so young and healthy. Or people who ask why I use a cane, why I have an escort, what could I possibly be doing taking all those medications; I'm obviously too pretty to have health problems.
And then there's work - up until I lost my job last year, I spent over a decade working in male dominated fields. Retail at Home Depot and Electronics Boutique (now Gamestop) where women are expected to be hot and stupid, and then as a Cisco Tech for ISPs where women aren't expected to be working at all.
At EB I was one of two female managers in our region, and our DM and RM both encouraged me to hire other attractive girls to work for the store - even with some of the highest numbers in terms of profit they thought more hot girls would bring in more business. After all, if the geeks responded to me by spending that much money in the store, imagine how much more they'd buy if the whole staff was female (it couldn't be because I'm good at my job, it had to be my looks and the fact that I wore dresses and skirts to work in). At the same time, they displayed sexist behavior, expecting me to be incapable of figuring out what was wrong when our computer system crashed or a shipment got fucked up. Oh, and no, you can't have an in-store security system; it's not cost effective even though your theft/loss numbers are too high because you are constantly understaffed and everyone is working by themselves for hours at a time. It was maddening to the point that I stepped down as manager before I had a new job and could quit.
At least I got mostly lucky in that my co-workers at the ISPs knew me prior to my being hired, and expected me to know my shit and be good at what I was doing. But our customers often fought back against explanations or assistance from a woman, especially if they met me or saw my picture on our webpage. After all, how can a woman, let alone an attractive one in a skirt, know how to fix their internet service? I must be either sleeping with the boss or the token female, don't you know... So even in a job where people knew I was good, I had to work harder to earn the same level of respect.
And men, holding the door open (and getting in the way of my cane), offering to carry my single bag, acting like I can't handle a few groceries without assistance is infuriating. If I know you and need help I will ask; if I don't, grabbing my bags to carry them for me isn't help, it's threatening. I'm perfectly capable of picking up 40-50 pounds of crap even with the cane provided it's properly loaded; there's a reason I carry the cloth grocery bags and pack them myself most of the time. I may seem small to you, but if I'm feeling good enough to leave the house by myself (rare) I'm quite sure I'm competent to get myself and my packages home safely.
It's impossible to win. I have privilege because of my perceived race/sexuality, my visible femininty. But I get treated as less than for the same traits. Why not pay attention to who I am, what I'm actually capable of (or not) rather than how I appear? Oh, right, we live in a world where women, especially "pretty" ones, are not equal or capable, we skate by on our looks, and at the same time if we're thin and seem young we can't be disabled.
And people wonder why I get so angry, why I treat my friends so well, what makes the family I choose, the "freak" scene such an important part of who I am. Simple - there I'm female, but I'm accepted for who I am, and not treated as a fragile flower or an idiot just because of it. Also, when I'm out at a "freak" event I can stomp on an asshat or quickly have him removed from the club - we take care of our own.
ETA: Being part of the freak community still has problems though - a lot of guys think I'm easy, a sex worker, looking for attention because of the way I look. Or they find my appearance/behavior threatening. Fortunately I decided years ago that dating someone who wasn't part of the club scene didn't work, so I don't care about the later, and I ignore the former or brush them off quickly. At least the intimidation factor makes it a bit less problematic from my POV - I have a level of confidence that I didn't used to have, and I'm not afraid to stomp feet with my spiked heels or throw elbows in the club when someone gives me shit (only after I ask politely once or twice). In some ways being a punk gives me a way to navigate the ups and downs of sexist behaviors that looking more normal did not.