Consider trying thrift shops, like Goodwill, especially if they have fitting rooms. A resale place, like Plato's Closest or Buffalo Exchange, might work too. They have clothes from so many different shops and brands all in one place. Keep in mind that some are better than others, so you might want to shop around.

The lady's section tends to have more interesting options, so take a look and grab a few things that appeal to you and try them on. Some might not fit great but others can be good. I've found quite a few things this way.

If you feel there might be some awkwardness shopping in the lady's section, in my experience people usually mind their own business and the employees are too busy stocking the shelfs to care.

Also, the cost is generally lower and they regularly have 50% off deals, so it's low commitment.