I think interesting outfits are about two things. First, what does the outfit suggest? Second, what does the outfit look like?
Outfits will naturally suggest something, whether you want them to or not. Some of the most stylish people I see in real life are not even into fashion. This includes the owner of an Italian restaurant near me, who wears big navy sport coats that don't quite fit, along with a gold Mariner-link bracelet. Or a barista who I thought wore Lemaire and Margiela, but actually alters thrifted clothes at home with her sewing machine.
Some years ago, I wrote a blog post about the charming ways I see people dress at my local bookstore. Specifically, the people who attend author talks — the old anthropology guy with a beaten Jansport and dusty cords. The exquisite ladies with fancy scarves. The tweedy bookstore owner.
Sometimes these clothes hint at something interesting about the person's inner life. The old anthropology guy may know a lot about linguistics. One can imagine the Italian restaurateur charming people every night in his sports coat and gold bracelet.
Second, what does the outfit look like? If we are talking about the stylishness of an outfit, then there has to be an outfit. A porn star may have an interesting life, but one can't say someone has a stylish outfit if they're not wearing an outfit.
Thus, for an outfit to be visually interesting, it helps to have certain characteristics. First is shape and drape (Does the outfit have a distinctive silhouette? How does the fabric hang and move?). Second, the use of accessories or layers (good outfits often have a "finishing layer"). Some will have texture, although not all outfits need them.
A lot of fashion content is about how to achieve a trendy look. Or how to dress in a way to project certain desirable attributes — wealth, fitness, success, respectability, etc. This sort of content can be fine, but doesn't always resonate with me.
At worst, sometimes this advice lands you with something like slide one. Some years ago, a stylist dressed Stephen Colbert for the cover of WSJ Magazine. I felt the clothes made him look less like himself — the minimalist, trendy look said nothing about his inner life except "I want to look trendy." I think this can make you look like an ambulant mannequin. The clothes suggest nothing except that you're a consumer.
IMO, a good outfit suggests something culturally and personally. It also looks natural. And it often employs things such as shape, drape, layers, and texture. The outfit doesn't have to look eccentric — although it can.
The best summation of good style comes from my friend and fellow menswear writer Bruce Boyer, who said, "Style is simply about being yourself on purpose." Sometimes this cultivation is a lifelong process, which is why it can take some experimentation.
Some years ago, a friend of mine in Vermont attended a workshop about growing flax, the plant used to produce linen. One of the attendees wore a gray tweed sport coat with a pink chambray shirt, jeans, and Wellies. I found his outfit to be very charming/ interesting.
You may have heard the potential for lowland snowfall tonight into Friday. This graphic summarizes the complicated weather setup that exists. Please keep us updated with what you're seeing in your backyard through tomorrow. You can submit observations through the mPing app! #WAwx