My situation sounds similar to yours, Dee. I live in the suburbs of a smaller, less cosmopolitan Canadian city. And it's really hard to know how people dress here, because you usually see them in one of three situations:
- In their cars. Where you can't really see them.
- Walking their dogs in the neighbourhood.or on the hiking trails nearby, or on their bikes on the trail.
- In their gardens.
In none of those places are you really seeing them in regular clothes.
Downtown, it's a mix. Mostly, the scene is very casual. But how many of those very casually dressed humans are locals, and how many are tourists? It's not always easy to judge!
The types of outfits I see sound a lot like the ones Carla describes. Slouchy oversized with shoulders, midriffs, or legs showing on the young. Pale tones. Mix of classic and schlumpy on the older women, with the odd artistic type in the mix.
I dress more casually than my aspirational style, not to fit in -- but for reasons of practicality. Because I get around on my bike, on foot, and by transit, I need weather-ready clothes and footwear that goes the distance. It's a constant balancing act, trying to figure out how to look like "myself" and also be dressed practically for my real, work-from-home, chores in garden, walking, biking life. My compromise really does sound like yours, Dee -- I'm in smart casual rather than gear for those bike journeys, which is a step away from the environmental norm but not quite as dressy as I might like.
For instance, my thinking might go as follows: "I'd rather be in a blazer with my jeans instead of a sweater, but the reality is, i need to squash my outerwear into my panier at my destination. So I'm wearing the sweater."
When I go to a larger city -- Vancouver, Toronto, Montreal, Seattle, anywhere else -- I tend to dress more as I would like, which is a slightly elevated version of what I usually wear.
Note: I do get comments on my appearance, whether I'm in the suburbs or in town. I sometimes think people feel freer to compliment or at least comment because I am on the smaller side. I seem non-threatening? Young women often compliment specific (trendier) items, like my jeans or footwear. Middle aged and older women usually comment on my hair, or some bright element of the outfit. I get a lot of comments on my Pom Pom London bags. Even in London, I had people on the tube asking me where I got my bag!