I wouldn't wear the cutoffs because they look sloppy. As a former software engineer, I think I'd likely wear a khaki skirt with a nice button down Oxford blouse and some sort of Wellington boot. In the winter I'd recommend a nice Stewart plaid skirt. I've even been known to wear my university...
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Oh, that's hysterical! I asked my friend the same question and he said the EXACT SAME THING! I told him I don't HAVE any overalls (strange, I know) nor a straw hat. Darn it! I knew my wardrobe was missing SOMETHING.
You're in Portland; those are easy to find. However, since you're not...
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How about some nice jeans - not cutoffs - with a nice long sleeved shirt and cowboy boots? Cutoffs and tank tops say "city slicker" from several miles off - especially when worn with cowboy boots. Why in the world would anyone want sunburn, ticks, stinging nettles, and poison oak? Real...