

I’m taking this same journey right now as well. I was in a similar situation as you (mostly plain shirts and hiking pants, think “Eddie Bauer”). I also really want to branch out to more interesting styles. The one thing I’ve learned from my partner is that layering is pretty much essential unless it’s a scorching hot day. You can also seriously consider the same sources for your current clothing (Eddie Bauer’s Women’s section is not half bad for comfortable things that fit well, if a bit boring). You should consider that bottoms are possibly going to be tighter in some areas and looser in others unless or until hormones or surgery happen. I have a wide and sturdy ribcage, so tops all feel like they’re too tight, especially at the armpits. Sizing up is an option, but so are looser cuts and stretchy materials. I find that I like a tighter base top and something loose to go over it like a hoodie, wrap, or shrug.
Experimentation is the only way to really learn anything. You can always try to abuse the Amazon “try 5 things out” nonsense, or find a shop that’s trans-affirming or go to the next city over if you’re shy and just try on everything until you find what you like. I have known people, especially my mother, to spend an entire day trying on clothing and buy one or two items. Or a dozen! I actually find the shopping and discovery part of this to be fun and a little relaxing. Think of it less as a chore or a scary task and more like a way to explore yourself and your identity, then make a fun day out of it!
Girl, get some tights. My quadzilla gravel cyclist legs look like thick thighs saving lives in a pair of yoga pants. Get the ones with the v cross at the abdomen and look like a lower body goddess. Top it off with a nice longline sports bra or a crop top and throw a camp wrap or something over your shoulders. Own that body you built and make it look good for you!