Maybe it's just that "The Lizzie McGuire Movie" had a huge effect on my childhood, but I've long operated under the assumption that wearing an outfit (or even a special piece) more than once is ~against the rules~.
This moment shaped my approach toward fashion more than I care to admit.
For the most part, striving to not re-wear the same outfit pushes me to be creative with my wardrobe. I love mixing and matching everything I own to create something new every day. There are, however, a number of reasons to re-wear your favorite outfit.
Sometimes, you buy a piece that only goes with one other thing in your closet. As you might imagine, these pants are a bit tricky to match with. Not only is the pattern a little daunting, but the thin fabric makes it hard to tuck a shirt into them, a trick I rely heavily upon. This shirt is one of the only things I own that works well with these pants.
I also tend to outfit repeat when I know I'm going to be seen by different people each time I wear the outfit. I wore this outfit first to work, then on a weekend outing with friends, and finally on a casual date. Each time I wore the outfit, someone was seeing it for the first time. In their eyes, I wasn't really outfit repeating.
Finally (and this is the most important argument in my case for outfit repeating), you should re-wear an outfit if and whenever you damn well please. Do you like the outfit? Yes? Great, then wear it as often as you'd like. Clothing serves a number of functions: to express ourselves, to cover our naked bodies, to signal belonging to a specific social group, etc. The most important function clothing serves is to please ourselves. If you like it, wear it. If you really like it, keep wearing it.
Someone recently told me about a coworker of theirs who, in an experiment to test peoples' awareness, wore the same outfit every day for a week. By the end of the week, they were still receiving compliments from the rest of the office, even though theoretically they'd seen the dress every day for five days. People are generally too unobservant to care that you've worn the same outfit multiple times, or even multiple days in a row. Just wear whatever makes you feel your best.
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