As I have discussed previously, there is a fine line between looking stylish and looking silly. Just as in the art of rhetoric and persuasion, it is necessary in the art of fashionably dressing to gauge your audience. An important part of fashion is analysis.
For example, in Europe, trench coats are all the rage. It is perfectly normal to see a person walking down the street in a long, beige coat. However, in Middle-of-Nowhere, Wyoming, where cowboy boots and denim and hats are the more common accessories, a trench would cause you to stick out like a sore thumb. You'd receive odd looks and may or may not be mocked.
When deciding what to wear, consider: Where am I going today? What sort of clothing will be appropriate in those situations? With whom will I be interacting?
For example, for a job interview, pass on the jeans and joggers. Go for a dressy look, not an artistically casual one. For a picnic, however, you most likely should dress down. In the places where you'll be, are tennis shoes the norm? Or will it be offensive to be wearing anything less than patent-leather loafers? Don't show up to a symphony concert in leggings and a long sweater. Just as you'd wear a swimsuit to the beach, you would not wear a swimsuit to a graduation ceremony. Pay attention to dress codes. (Tip: it's always better to be more dressed up than too dressed down.)
Another, oft-cited example is Europe: don't wear cargo shorts or Nike sneakers or hoodies or fanny packs...because it will make you stand out as an American tourist and you will be in greater danger of theft from pickpockets. Do your homework, blend in.
By "blend in," I do not mean "look the same as everyone else." I simply mean, play by and follow the rules of the society, for your own safety and sanity as well as others'. You can dress in your own style, but rein it into the appropriate category for the circumstance. True fashionistas can make any type of outfit their own and dress appropriately without losing that unique touch.
Be bold, but not insensitive. If you don't mind looking moderately to extremely absurd, then wear that trench coat in rural western America. But if you'd like to dress smartly, observe the style dynamic of the area first. Partly, it's respect for local culture and, partly, self-preservation. Push boundaries, but do it with sensitivity and foresight.
