Should I size down in oversized streetwear?

Usually no. Most streetwear tees are already cut oversized at your true size, so going down typically gives you a fit that looks more retro or fitted than the design intended. The exception is if you specifically want a tighter silhouette, like a 90s set-in sleeve look on a modern oversized cut.

Stay true to size if you want the intended fit

Brand size charts for oversized streetwear are built assuming you wear your normal size. The pattern adds room to the chest, drops the shoulder, and extends the hem from there. Picking your usual size gets you the silhouette the designer drew.

Size down if you want a fitted retro look

Some people want oversized cuts to read more like a relaxed regular fit. Sizing down gives you the drop-shoulder construction but with the chest and body sitting closer to you. The result feels more 90s, less 2020s streetwear. Valid look, just different from default.

Size up if you want extreme drape

If you want the tee to hang almost like a long shirt, with the hem mid-thigh and the shoulder seam halfway down your bicep, size up. This is a deliberate look, not a fit accident. It works best on taller frames or under longer outerwear.

How to actually decide

Check the brand's chest measurement against a tee you already own and like the fit of. Measure pit-to-pit on a flat surface. Match that number, not your shirt label. Size labels vary between brands, but chest width does not lie.

One thing to remember

Sizing down does not reduce the shoulder drop. The drop is built into the pattern. A smaller size gives you a smaller drop only in proportion, not in placement on your body. If you want a regular shoulder, look for a regular-fit tee, not a smaller oversized one.