Let's be clear about "looking dated"... I often receive compliments (from elder gents and young girls) for a 90's Hickey Freeman suit having the exact same "dated" features: big rounded lapels, closed quarters, old-school notch, etc. (But the buttoning point is higher, and the jacket is short - then it looks fashionable in some respects.)
I wear the suit (perfectly fitted) with fancy Brioni shirts, colored cufflinks, vivid ties, and quality boots - all this for "serious" occasions. The suit is dated for SF standards, but everybody likes it.
Conclusion: 1) old can be likeable, or 2) non-SF people don't really perceive what is "dated" clothing, as long it's fitted and paired with stylish things.
I wear the suit (perfectly fitted) with fancy Brioni shirts, colored cufflinks, vivid ties, and quality boots - all this for "serious" occasions. The suit is dated for SF standards, but everybody likes it.
Conclusion: 1) old can be likeable, or 2) non-SF people don't really perceive what is "dated" clothing, as long it's fitted and paired with stylish things.
