A familiar frisson accompanied this action, the same as I felt after using the men's room at the theatre once. (It was an emergency more than a whim: my film was in progress but another well-attended movie had just let out. Both men's and women's restrooms were packed to the gills, but constant maddening experience has demonstrated to me that the men's line moves faster due to anatomy and a desire not to be thought gay. I waited, staring firmly ahead, in a line of men and children, suspecting that each saw me and resented my ability to invade their space without consequence. It smelled terrible.) After assuring a reasonable fit in the ladies' dressing room (though, like all jeans, these gapped at the back), I brought my purchase to a pretty young clerk. As she rang me up with a retail smile, I envisioned her being blown away by my poker-faced daring, and later telling her friends of her envy and admiration for my style. (I probably shouldn't admit this, as it appears conceited beyond belief; in my defense, I am aware it is a fantasy. This is not what I believe actually occurred.)
I rarely buy men's clothes since I went femme, so this purchase was tinged with nostalgia for teenage dykehood. The feelings of danger in crossing a gender line, I find, vary considerably with the circumstances. The two-level design of the store here forced me to cross the border very publicly, but many stores separate men's and women's sections by inches. I've never been accosted, asked to leave, or treated with hostility while browsing for men's clothes, but I suspect the same would not be true if I were male-appearing and looking at skirts. I feel it can be advantageous to roleplay that, perhaps, you are shopping for a gift for a father, brother, or boyfriend. Or just adopt the same demeanor you'd cop if you wanted to shoplift: you belong and your actions are normal and blameless.
I think women should have the experience of shopping for and wearing men's clothing, not because it is transgressive, but because I think women should understand firsthand what it is like to wear something which has been designed primarily to fit and be comfortable on a broad range of bodies. How it looks is something of a tertiary concern for men's clothing, following well after function and comfort. By the same token, I think men should experience buying and wearing women's clothing, due to my deep-seated hatred of men.

Basically, the rule is that flaws--those aspects of your body that differ from a purely hypothetical and subjective female ideal--must be concealed for the sake of public decency. Remember, if you're female, the visible parts of your body belong to a sort of civic trust, and as such are subject to continuous urban renewal and beautification efforts. The process of disguising the unacceptable reality of your horrible body in a decorative way is known as "flattering", from a term meaning an insincere compliment delivered with an ulterior motive.
Skinny jeans, leggings, and jeggings are unflattering because they fail to conceal the shape of the leg, belly, and buttocks (the most awful parts of the woman, after her terrible genitals), forcing people to view the shape of female bodies which are wider or differently proportioned to the ideal. I plan to wear them with boots. Incidentally, the price of jean-colored spandex sewn into the shape of some leggings is slightly greater than the price of men's jeans. Both are about $15 cheaper than inexpensive women's jeans.
So as you can see, I'm a fashion fucking rebel. But already, inadvertently, I negated any transgressiveness of either of these articles of clothing when I bought them in a chain store, with money, and then took them home and put them on my young white pretty body. Whether I or anyone else wants it that way, that'll always be a fashion "do".
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