A big part of dressing is deeply rooted in the fašade of being flattering to other people. Dress like this to look thinner, wear this to look taller, and do not forget about all the "don'ts". I think part of the problem with what is flattering and what is beautiful has become so incredibly skewed. All things are not beautiful to everyone even though all things have beauty. One person's flattering is another person's pain in the ass.
We all have an opinion on how someone else should live their life, dress, eat, talk, and act. Some of us voice it way too much while others are smart enough to keep it to themselves which is actually pretty wise considering thoughts are fleeting -- how one feels about something today can be totally different tomorrow -- and it is not necessary to share every thought we have.
When it comes to comfort we should be able to wear what we want when we want but society has constraints everywhere -- showing up in your flannel pj's to a wedding would be wrong no matter what your size -- and would probably be one of those rules we should follow. That being said, I think as a society we focus too much on what someone else is wearing and whether or not it makes them look good. This is determined by our internal set of rules and the rules that have been pushed upon us year after year. How many times has someone said, "You would look so much better if you..." cut your hair a certain way, wore a certain type of clothing, etc. When we get hurt or angry they hit us with the "I only tell you these things because I love you (I'm your friend etc.)"
All cultures have had their ideals for beauty and for dress -- many we would consider extreme. I do not think there is anything wrong with a standard of dress per se but there are so many opinions in the pot and everyone thinks their opinion on what is right should be expressed because so-and-so would be so much happier if they followed the rules of what is flattering (that was sarcasm in case it was not coming across in the text). Instead of being nice to someone it becomes more important to tell them what they are doing wrong, usually hidden behind the thin veil of friendship.
I can admit I am guilty of it. I have a friend, let's call her Molly. In my opinion she looks phenomenal with dark hair and dark burgundy highlights. I love it and have told her so on numerous occasions, which is fine. This summer she went blonde. I hate it. I did not come out and say I hated it. But I was not supportive of her choice to go blonde either and pretty much implied I hated it with comments like, "when are you going back to the dark and burgundy" and "I liked the dark better". Which was true but it was still a thinly veiled insult on the way she currently looked. As the summer continued she added more and more blonde highlights and I kept thinking she looked so much younger with darker hair, "Why doesn't she just go back."? Then it dawned on me. She is not here to please me and look good for me. If this blonde hair makes her happy then I should be happy for her. Who am I to interfere with her (not mine) happiness. The color of her hair does not change that she is my friend or that I love her. And my love is not contingent on how she looks -- otherwise it is not love, right?
I am sure there are those "friends" out there who are thinking, but I am just being honest, if I was a real friend I would not let her walk around like that. If we are real friends we would keep our mouths shut -- real friends pull people out from in front of a moving vehicle, they don't belittle their fashion choices. If you are embarrassed by the way your friend looks then you are not really friends. You have two choices, you need to get over it and be supportive and truly loving or find a new friend who fits more in with your important standards of what is flattering. Good luck with that.
This summer our household has been watching more than a few renovation shows and I cannot remember who said this and I am really paraphrasing here but one designer said in terms of paint choice, it is not the color change that is hard to accept it is the overall visual change that our mind has difficulty with. I think this can be applied to many changes in our lives including friends and hair color.