I have never been married. However, my primary female friend (my best friend to be more precise, not a lover) wears dresses, tights, highly attractive and mature clothing. For a 27yo, she is very stylish. Most of her stuff comes from expert shopping, thrift stores and gifts I purchase her (for example, I purchased a dead stock D&G gown for her) and also becomes part of her stage wardrobe. She is a professional musician and has performed in everywhere from the lowest of dive bars, to classy joints, to high end venues. She always wear a dress or more formal clothes while performing. But even if it's a simple date at the movies, it's not uncommon for her to wear professional clothing.
I have another female friend who works as a customs inspector. She wears cargo pants and a uniform blouse to work, so when she gets off work, it's jeans, sweats, tee shirts and sneakers. I have a great deal of respect for the work she does, and I remember having a job with a mandatory suit and tie job. When I had that job, I changed often into my bedclothes to hang around my apartment, so I don't really fault her for being uber-casual after work. And quite bluntly, I care more about the person than what they are wearing.
The first girl practically expects me to wear an overcoat, sportscoat, tie (often a bow) and nice shoes. The second, likes me however I dress, but when I see her, I tend to dress "down" because I realize that she has neither the desire or money to dress up after work. She owns one dress, bought for a wedding.
As for being told to dress down, often it's mommy dearest who says, "You shouldn't wear a bow tie to the movies" or "Don't wear a suit to go out to a nightclub". Mother unfortunately grew up with substantially less prominent sartorial influences and she dislikes it when she says I "overdress" for things like supper, travel, family gatherings, etc. I'm sorry, but if somebody's getting married, Easter weekend or a long distant relative is coming to visit, I'm not putting on the dog, I'm putting on appropriate clothing.
Thomas