I tend to flair my cuffs back whenever I wear clothing that has them, is this a bad habit or is it nothing to worry about?
There are some pretty disparate views on this.
So far as flaring them back (Which I’m presuming is just “rolling” the cuff of the shirt once), I think it’s fine, depending on the context. Obviously, when wearing a suit or in a more formal situation, flaring the cuffs back is a little bit too much to really be respectable. Similarly, on a shirt that is very baggy, flaring the cuffs back might make the shirt seem much more bulky than necessary. Other than that, however, it’s probably just personal preference, and to my knowledge, not really a violation of any sort of fashion rule.
Just to go ahead and cover my bases for potential future questions, rolling your sleeves up in general applies to this rule: do it in a casual sense, and ideally when it looks proper with the shirt. There is no minimum roll-up limit or anything silly like that- feel free to roll it up above or below the elbow, as high as you feel comfortable.
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