I think many people associate being comfortable with not looking put together or cute. And may believe that those two things cannot exist together in an outfit. I wholeheartedly disagree. There are so many ways to dress comfortably but not look messy or sloppy or dress in clothes you don’t like. Wearing a t-shirt, shorts and sneakers seems like an outfit that doesn’t need much thought put into it, or one that isn’t fun to wear but that does not have to be the case. Graphic tees are everywhere now and can be a great way to make a comfy t-shirt more interesting. Same goes for sneakers – boring ol’ athletic sneakers are not the only options out there anymore. There are a ton of printed sneakers in all patterns and colors (and all price points) that are comfortable and can elevate your outfit. Adding a hat or statement bag can be another way to make a super casual look more fashionable and chic, but not always necessary.
Try to think of your casual and comfortable looks as just as important as your work looks or evening looks and you will slowly build up a wardrobe of things you love to wear. And then no matter the occasion – a day in the park, running weekend errands, going to an amusement park, etc – you will feel just as fabulous.