Self-esteem issue, too shy to wear what I want

I'm 23F and lately I've been thinking about how I look and how I want to look. I recently read a quote about beauty on the Internet: whatever you can change (and want to change), change it; whatever you can’t change, own it.

Anyway the thing is, I'm afraid of making my choices on what to wear. Since I was young, I've always been SUPER shy aboout expressing my preference about anything to others. Movies I like, books I like, or even a specific item in a bakery. I literally feel anxious when eating out with others; for example at a bakery or a bubble tea place, I would always let others make their selection first, then I'd pick the same option as theirs, even though in my head I have an eye for something else.

As for clothing, I never really go shopping on my own. I don't go shopping a lot, and pretty much all of my current clothing were picked out by my mom. I did pick out my favorite from the clothes she bought, but I've rarely ever picked my own from a store.

These days there are somet things I saw online that make me really want to wear them. I have never tried them before. But I've spent hours looking at them and admiring how nice they look on the pictures. I've always been wearing plain pants, but now I want to wear long, flowing skirts. I've always tied my hair up with a black hair tie in a simple low pony tail, but now I want to wear a french twist using a gold metal claw clip.

I just don't have the courage to buy the items I like. First, I'm scared that they're too beautiful and I would have no occasion to wear them anyway. I want to dress beautifully, yet I'm too shy and uncomfortable at the thought that they might draw attention, even if it's positive attention. I'm shy of being different from my former plain look. Then, I'm scared that they may not actually look nice on me. I'm scared of being judged for my preference on clothing and appearance. Just like I'm scared of being judged for my preference about anything else.

Second, this is funny, but I'm scared of being "trendy". I don't think there's anything wrong with wearing trendy clothes at all. But there's still something that makes me feel hesitant to buy something "trendy". In reality these items are simply attractive to me; it has nothing to do with its trendiness, I just simply like the style. Maybe I'm scared of matching clothes with others. Maybe I'm scared of being thought of as "trendy".

I heard that it's a self-esteem problem when someone is scared of dressing their best. How could I improve my self esteem on this? I just feel like I'm wasting time looking up clothing items online, craving them and never actually have the courage to buy them lol.