Putting together a cute outfit can be fun and make you look great but if you don't feel comfortable in it then you simply won't wear it. Comfortable doesn't mean sweats and running shoes. You can still look great and be comfortable, it just takes some effort.
The most challenging part of making an outfit comfortable is the footwear. There are loads of wonderful shoes available that look amazing, but they aren't so fantastic when you put them on your feet and try to walk in them. My personal test to decide whether or not I should keep footwear is to buy the shoes, leave the tags on them and then go for a walk on my treadmill for at least a kilometer. If after a 1-2 km walk I don't have any blisters or soreness I keep the footwear. I've taken many gorgeous shoes back to the store after my treadmill test. It's sad, but in the end I've decided I want to be able to wear my shoes, not just look at them in my closet.
Here is an outfit I wore when I went to Europe this past year. At the last minute I switched out the boots for some that were more comfortable. I'm glad I did. I literally walked for hours and hours all over London in this outfit.
Yes…that is my sister with me in the shot : ).