Most Helpful Guy
Only intimidating to people who are not used to it. I know what you mean, i feel underdressed and embarrassed in sweatpants if I'm not going to the gym or for a jog.
That being said it all depends on what you're doing. If you're going to the grocery store, intentionally getting dressed and dolled up might be overkill compared to going out on a date.
Dress for the occasion.
Most Helpful Girl
Always being dolled up can send lots of different signals. People interpret it in different ways. Personally, I'd think that:
A. This person likes spending time on her beauty and makeup, it's something she enjoys.
Or B. This person can't leave their house without looking their best because they are insecure.
.. It actually depends on the vibe they give off. I never really judge, these are just the random thoughts i get. I think some could misunderstand point A as someone who is stuck up, even if that's not even the case.