Nope. most summer dresses aren't really "dressing up" to me. Once guys realize that a dress is just throwing on one giant piece of fabric instead of having to match with pants/shirt/belt etc. it's much more casual lol.
If you're wearing heels, makeup, dresses, and belts with accessories and stuff every day I would consider that "dressing up" all the time. I enjoy a woman that puts effort into her daily life to always look good though. I think it's an attractive trait to always put your best foot forward, even if it's just to the grocery store.
It's not weird but I personally would find it a turnoff. I prefer a more practical style on a girl that is more appropriate for am active lifestyle. Basically if you tell me you have to go home and change every time I ask if you want to hop on the back of my motorcycle or go play laser tag or something else along those lines because what you're wearing isn't appropriate then just... no.
Not at all. It's who you are and wearing what makes you feel good and more confident is what you go with. In this case, it's wearing dresses. I feel just as you do and wear a dress or skirt just about every day, so you've got plenty of company. Enjoy!
I wouldn't necessarily use the word 'weird' but it would probably come off as she's trying too hard to impress other people. Dresses are great and some off them are really comfortable but it's normal to have lazy days and want to wear more comfy, less dressy clothing.
No not in the slightest.. For most of my working days I wear a business suit (jacket & skirt) on others I wear nice fashionable dresses.. It's purely my style and what I feel comfortable in.. Do not allow anyone to make judgement about you.. Just be yourself.