You shouldn't need to listen to anyone or wonder if something is trendy to dress up. Honestly I don't really care if someone might consider the stuff I wear to be outdated. Some of the more recent trends are so stupid like when bucket hats were a thing, excessively layering your clothing, usually with huge denim jackets and who knows what else underneath, and now I guess it's sweatpants and baggy clothes in general. A lot of these trends are pretty trashy looking imo and are almost always geared towards younger people. Whatever "fashion" is, it doesn't exist anymore because most people almost exclusively "dress up" only to be comfortable. I actually prefer wearing lighter yet rougher materials since it keeps me more awake and aware and I find it easier to focus when I'm not covered in fluffy warm cotton all day. Obviously, if you're Lady Gaga or something then everything's different and you can wear all the furniture and meat dresses you want. My favorite outfits are denim cutoff shorts with the tassels or white khaki shorts with a solid color T/v neck or Hawaiian button ups. I really enjoy flashy stuff with cool patterns or bright colors. I also like some of the more dressy uppy stuff. For cold seasons, it's pretty simple I usually just go for gray or black pants with some kind of jacket