Key: add a "high / low" transition piece that combines formal and informal qualities.
Going to the "Bohemian Rhapsody" movie tonight, I felt compelled to wear my grungy/cool Pink Floyd t-shirt, the closest I can come to Queen. (Really, it's a tragedy that I don't have a Queen t-shirt, but there it is.) I also wanted to try out a black-skirt-and-boots combination for a possible modeling look, but I didn't have enough time to do both. So how to combine the the elegant boots and faded top?
Here my transition piece is the jacket, casual in denim but dressed up with faux fur details and a tuxedo cut. Of course, I'm exercising tight color discipline, sticking to blue and the black to ground the outfit. Can't have everything wandering all over the map. T-shirt, jacket, and hat all from Goodwill.
If you want to bridge high and low, find something that combines them both. Look for pieces with a casual shape but high-end materials or a formal cut with a relaxed fabric or a structured shape with a faded print. If you try the strategy please let me know in the comments how it works.
As a coda, I couldn't help adding my vintage mink hat. It's a perfect match for the fur on the jacket. Not sure whether this is too over-the-top. But they say you can't discover the edge of the envelope if you're not willing to push it a bit. Hope you all are having a wonderful day.