Next to “old” (as in, “that style makes you look old,” or “that style ages you,” the next biggest put-down in fashion is the term “unflattering.”
“Unflattering” can mean:
Too big or baggy, meaning “we can’t see the shape of your body.”
Too small or tight – meaning “we see parts of your body we’d rather not see.”
Out of proportion with the wearer’s stature, meaning “we think you look short” or “wide” or “fat” (never “you look tall” or “you look slim”).
Out of proportion with the wearer’s secondary sex characteristics, meaning “we can’t make out your breasts, butt, hips” etc. (This includes “the male gaze.”)
Shaped or cut so that the desired body form is obscured, meaning “we want to see a normal body,” (whatever that is) or “we want to see you the way we usually see you.”
Don’t surprise us or challenge us, whatever you do.
“Flattering,” then, comes down to how others see us. After all, when someone flatters you for your brains, looks, accomplishments, character or any other trait, they’re really talking about their reaction to you.
You can’t flatter yourself.
Of course, you can wear and enjoy things that you think look good. You might wear those garments hoping to get compliments – fishing for flattery – or you might wear them because they make you feel happy, powerful, smart, kind, capable, or any other way that you want to feel. Or maybe you don’t want to feel anything in particular – you just want to put on comfortable clothes and get on with your day.
Which all leads me to this look:

This top is the Brasov Wrap Top from Itch to Stitch. The pants are the “Discover Something Novel” pants from The Cutting Line. One guess which is the “flattering” and which the “unflattering” garment?
This top is designed to be flattering – a wrap style in stretchy knit that sits close to the body. It’s designed to make breasts and waist and hips stand out – textbook “flattering.”

The pants are the opposite – they sit away from the body, obscuring legs, hips and butt. Their width actually makes it hard to imagine the body parts inside. Surely I have legs and a butt, but where?

How dare I wear something “unflattering!” Don’t I realize that my body should be on view as much as possible for other people to look at and enjoy (as long as it’s conventionally “attractive” that is)!
Today I wore these pants to go shopping. I picked up some buttons and other items at a vintage store. I bought a sweater at a boutique. I stopped in an art supply store. I got groceries. And in all four places, I got compliments on these pants. WHAT? Aren’t they “unflattering?” How can someone lay some flattery on me then?
Because these pants are interesting, that’s why.
What’s more, I wear them for me and for no one else, and there’s magic to that.
Most people walk around in a state of total conformity – normcore jeans for miles, maybe some leggings or yoga pants at a stretch (and almost always in black) – and they are all ignored. Seen it a million times, dah-ling – and will see it a million more. But wear something different, and people react. Maybe the garment elicits an emotional reaction – makes someone smile, perchance, or makes someone frown – or maybe it makes someone think. Maybe these pants make Gen Xers like me nostalgic for the 80s. Or maybe someone thinks a Gen Xer like me is stuck in the past. Who knows? Who cares?
Anyway, it’s better than plain old flattery any day.
And if you really want someone to react, when they compliment you on your traditionally unflattering garment, say “thank you, I made them myself” and watch their eyes bug out of their heads. And enjoy the satisfaction of that!
My policy is wear clothes you feel comfortable and appropriately dressed in. I have had those sort of ‘like’ comments as well but suspect they mean ‘how cute and brave of you to wear something so odd at your age’. The majority of the population have not made any of their own clothes though and I am at an age when I don’t care that much what people think.
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Totally agree that these kinds of complements are about reaction to something different. I think it’s fun to shake things up.
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I like your pants. They are a certain style that look really comfortable and you also picked a wonderful fabric. We should all wear what we like!
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Interesting thoughts. I am in an environment both at work and where I live where people don’t comment on appearance much, and it’s actually great.
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