I have Bing Crosby to thank for this look. The expression “Canadian Tuxedo” is due to Bing being refused service at a hotel in Vancouver, BC due to his all denim ensemble. Levi’s heard about it and presented him a tuxedo made of denim.
I have worn denim on denim a couple of times (here and here), but I have never paired a denim jacket with denim. I was wearing this denim jacket with colored denim when I tried on these slim boyfriend jeans and I loved the look so much I left the store in my new jeans. It brought back cutting the tag in the dressing room with my mom when I was a kid (and what my son often does as he is so excited to wear his new item). That look included a striped shirt and striped flats.