Well, often I go for a retro/smart, and casual, look. Often though I resort to what's cheapest. Occasionally I'll wear a witty shirt like when going to play DnD.
As an example, my common outfit for Mondays, Wednesdays, and Fridays is as follows: Beige pants (can't stand jeans), white polo shirt, then black silky dress shirt (I don't actually know the material, it just feels a lot like silk.)
When going out I usually wear my Tilley hat. If it's really cold, I'll wear an overcoat with a wool scarf and leather gloves. If it's chilly out, a leather jacket with a wool or silk scarf depending on the wind chill, and leather gloves. If it's mild out, I wear a denim jacket with a silk scarf. Summer hasn't arrived yet and since this is a relatively new style for me I have no clue. All seasons I wear a pair of hiking shoes. (They're durable like boots, but shaped like shoes with the part at the ankle only a bit higher than usual.)
Oh yes, and I always have my hair in a pony-tail, unless I'm lying about in which case that's simply an annoyance. And I'm usually wearing an old watch with a really crappy watchband that will soon be replaced, hopefully.
That being said, I'm looking into obtaining some older clothing. I wouldn't mind finding a vest or waistcoat somewhere...