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The UAlbany Crossing 
This might seem like a stupid question but I’m going to ask it anyway. I am the most comfortable when I’m in jeans and a t-shirt but I still really love wearing heels and dresses…do I have to label myself something different every time I get dressed? Like “today I’m masculine” but “yesterday I was feminine”…is it ever that serious?
No question is ever stupid! And no, there is no need to label yourself every time you dress a certain way unless you want to. I am the same way as you, I usually feel the most comfortable in jeans and a t-shirt too, but I like dressing up also and when I do dress up its usually extra feminine. So, unless you want to label yourself every time you dress in a different style, there really is no reason to put so much pressure on yourself/ to label yourself. Style and Different ways of dressing are things that are ever changing and also they are usually very unique and specialized from person to person. Both style and the way you dress at times can help us better represent ourselves and at the same time they can sometimes help us better fit into societal “ideals” etc. What I’m getting at is that most people change up there style on a daily basis, so feel free to change from a more masculine style to a more feminine style without worrying too much, because people do the same thing every day, you don’t have to label yourself overall as a more masculine or feminine dresser you can be both/somewhere in-between. I hope I gave you the answer you were looking for, let me know if I said anything confusing and also let me know if you have any more questions, Thank you for posting in the advice section! =)