"WHEN I AM AN OLD WOMAN I SHALL WEAR PURPLE
With a red hat which doesn't go, and doesn't suit me.
And I shall spend my pension on brandy and summer gloves
And satin sandals, and say we've no money for butter.
I shall sit down on the pavement when I'm tired
And gobble up samples in shops and press alarm bells
And run my stick along the public railings
And make up for the sobriety of my youth.
I shall go out in my slippers in the rain
And pick the flowers in other people's gardens
And learn to spit
"You can wear terrible shirts and grow more fat
And eat three pounds of sausages at a go
Or only bread and pickle for a week
And hoard pens and pencils and beermats and things in boxes
"But now we must have clothes that keep us dry
And pay our rent and not swear in the street
And set a good example for the children.
We must have friends to dinner and read the papers.
"But maybe I ought to practice a little now?
So people who know me are not too shocked and surprised
When suddenly I am old, and start to wear purple."
- Jenny Joseph
One of the poems my mum loves; you made me think a bit of it. It really depends on your priorities, you know? Are you trying to blend in, to "put your best foot forward" or are you trying to do whatever pleases yourself? Most of us generally end up finding some kind of balance between the two that we can live with.
I have a style that is distinctly my own, but I'm also choosing colours that flatter my skin tone, cuts that work with my body shape... Yellow, orange and red make my skin look awful, while blacks and dark blues and greys are wonderful on me. I know that wearing a deep collar without a necklace makes me look pallid and washed out, and that low round necks are never going to work for me because I have nil cleavage. I can't wear skinny jeans without calf-high boots to cut up my legs or I look like I'm on stilts. Makeup that highlights my eyes is far more effective than highlighting my lips.
There is unquestionably a skill to "looking good" in terms of what our culture deems pleasing. And depending on your goals it can be a useful one to learn.
However, I suspect that that lady would think I wasn't "putting my best food forward" either. Many ladies seem desperate to get me in a dress and a load of makeup. On the other hand, the ladies I like are more interested in getting me out of my clothes all together... So it does depend on things like target audience (yourself, your friends and family, co-workers, potential romances, etc.) and what you are comfortable with.