My goodness, it’s been a while since I did one of these! I’ll try and get my WIWT shots back on a more normal schedule.
I’ve been experimenting with the polarizing denim-and-blazer look a bit lately, and while it may not ever become a central part of my style it’s worked out better than I initially thought. As with many menswear-y things, getting this look to work is more about finding the right pieces than anything else. It needs to be the right pair of jeans and the right jacket to keep the formality level similar, otherwise it starts to look too much like a mullet.
I tried to lean into a bit more of an Ivy-inspired look here, or at least what I’d envision some theoretical prep kid wearing. Mid-60’s style denim with a mid-rise and tapered leg, OCBD, patch-pocket herringbone sportcoat, and a pair of suede longwings to finish it off. Perhaps a shetland sweater would help bring it all together, but lord knows it’s not nearly cold enough for that here.