Dude, stick with the classics and you'll look fine, no matter what your age.
That means:
- Loafers (without socks if you're wearing shorts)
- Classic tennis shoes (think Jack Purcells - again with no socks or super, super low socks if you're wearing shorts)
- Classic dress shoes (the ones without the pointed toes, and not with shorts)
- flip-flops (no jesus sandals please!) if its a hot day out
Speaking of shorts. Lose the cargo pockets and go with a fitted short that stops at the knee. Imagine taking a pair of work pants and chopping them off at the knee. That's how baggy your shorts should be.
Full-disclosure: I've subscribed to GQ for 5 years, so take my advice for what it's worth. On that note, I'm also hoping you tuck-in your button-down?
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