I don't consider myself fashionable or fly, but...
1) Do you get all your clothes tailored
Overcoats, suits, dress shirts, dress pants... Definitely.
2) Where do you mostly shop online?
Like I wrote above, I don't think of myself as fly or fashionable, BUT my entire wardrobe comes from Japan or South Korea. I get compliments on stuff even though it's not European designer, but simply 'cause it's different. I'm sure you could find stuff online these days.
3) Any secrets to keeping clothes looking new when washing/drying?
I turn everything inside out before washing. That's the part that needs the most cleaning anyway. I only air dry my jeans. Jackets, sweaters, overcoats and dress clothes used to go to the dry cleaners, but I'm gonna start hand washing them next fall.
I recently noticed my mom puts a load of clothes in the washing machine, lets it fill up, then uses the water and soap to soak and hand wash delicates and sweaters. Smart as fukk.
4) What articles of clothing do you spend the most on?
Coats, dress shoes and dress pants.
I only wear solid color t-shirts. I think I would get them at like 3 for 700 yen each, but they're for the Japanese market, so even though they're hecka cheap, they look nice and last. I only wear Edwin jeans and khakis.