When I first started changing my presentation, I did feel stupid. Somehow it's easy to get so used to the way things are that changing feels ridiculous. At the end of the day, they're just clothes (or a hairstyle, or finger nails, name, whatever) but it definitely doesn't feel that way. If you find a way to not feel that, let me know.
But I will say: that feeling goes away eventually. If you're drawn to present differently than you do, take small steps to slowly expand your comfort zone. I started by wearing feminine clothes for at-home dates with my partner. One of my female friends asked to paint my nails once and gave me her nail polish to keep--since then my nails have been painted almost 24/7. Eventually I bought women's jeans--no one could tell the difference but I knew and that made me feel better. I wear mascara occasionally. I got my ears pierced and most of the time wear androgynous earrings. I switched out my baggy t-shirts for more form fitting ones. Once I got comfortable wearing dresses at home, I started wearing them to friends' houses. Once I was comfortable there I started wearing them anywhere I felt like. Etc...
Don't overwhelm yourself, take it slow. Push your comfort zone but don't go so far so fast that you feel bad, it should feel okay the whole time. And if it's too much ever, just slow down even more or stop entirely for a bit. No need to rush, just figure it out step by step