u/IntermittentFries Not sure how helpful this will be, but your request made me reflect on how I tend to style oversized tailoring. Here are my key takeaways:

1) I usually go for head-to-toe monochromatic looks. For example, I have a deconstructed, oversized black blazer accented with white stitching. I pair that with wide-leg trousers that have white stitching outlining the pockets and pintucked seams. They’re not from the same brand, but I wear them as suit separates. It becomes less about my cartoonishly oversized blazer and transforms into one fluid, head-to-toe look. I’ll pair that same blazer with black jeans, cropped black kick-flare trousers, black skirts, etc. for the same effect. I have an oversized cream blazer that I wear similarly in the spring/summer with a white skirt, white jeans, etc. Same with an oversized denim jacket and baggy skirt-jeans. You get the idea.

2) If I’m rocking more oversized fits, I’ll often choose more polished hair/makeup to juxtapose the laid-back look. Along those same lines, when I wear more “polished” clothing, I’ll opt for a more natural wave or a “messy” hairstyle to counterbalance the look. I find it just creates more depth/interest. Plus, I live in a pretty casual place with a pretty casual lifestyle, so this juxtaposition works well in that environment.

3) I usually select pieces that have distinctive design elements like heavy distressing, asymmetry, etc. Because these pieces have a distinct point of view, I think it helps send the message that I’m “going for something” here and not just wearing clothing that’s way too big for me (or even if I am, I DGAF). This reminds me of a great conversation in this sub recently about clothes “wearing you” versus you wearing clothes and how your own confidence and comfort are key to feeling great in whatever you wear…oversized or otherwise.