This year my grandkids switched to a new high school. After a couple of months the other teens started commenting to them that their mother was so beautiful were they rich? My grandkids laughed because their family is definitely on the lower level of income. They asked, "Why would you think we are rich?" the answer was, "Your Mom always dresses so nice. Our Moms just always wear pajamas." Now their Mom was dressing casually but instead of pajamas she wore jeans that fit her nicely and a shirt or sweatshirt that was a pretty color or interesting pattern, nothing actually fancy, but an outfit that showed she had respect for her worth and that of her children.
I know that stretchy leggings and a baggy sweatshirt or tee is comfortable. I know that most Moms and Dads are very busy people and aren't trying to impress anyone with their looks. But it takes the same amount of time to put on attractive jeans and shirts as it does sloppy looking ones.
Our clothing certainly isn't the sum of our worth but how we present ourselves in public does give off a message of how we value ourselves and how we respect the value of the other members of our family. You can't "judge a book by its cover" but the cover will usually give you a fairly clear idea about what is in the book. Sometimes we don't care how we look because others have not seemed to value us. But I have found in over forty years of mentoring young people that if you present your outward appearance as valuable, people will begin to respond to you as if you are valuable. And Dads, if you're still wearing what you wore in high school you need to update to the twenty-first century for the sake of your wife and kids. My grandkids got honor and admiration because of how their Mom dressed in casual clothes.
One more alert. Don't try to look like you are sixteen or dress like you did at sixteen. Teens don't really approve of that though they probably won't tell you in order to save your feelings. There is such a thing as stylish but age appropriate. Besides, who wants to see fat or wrinkly legs and other parts of the body. Camouflage those areas and accent your friendly loving face and eyes. People will respond positively and your teens will be proud of you.