For Fallout 3:
My casual/default outfit is a modded high quality version of the Armored Vault 101 jumpsuit which I wear almost all the time with a hunting rifle on my back. I like keeping the Lone Wanderer identical to the promotional art and trailers.
When I get into heavy combat situations, my go- to armor is the Prototype medic power armor. Considering that I always play good karma on the side of the Brotherhood, this armor just made sense to wear. It's powerful and unique, having the ability to administer med X when your health bar drops low as well as having an on board voice that warns you of enemies near by.
For New Vegas:
I stick with wearing any sort of wasteland type outfit but gradually getting more formal until I'm constantly wearing suits. This shows my overall success and progress in the Mojave. I also tend to wear suits whenever I'm on diplomatic quests.
When I'm in heavy combat, I use the Gannon family Tesla armor.