I really try to replace the word "can't," both in my thinking and speaking. It's easy to say, "Oh, I can't wear short skirts," but that's neither true nor fair and, frankly, I think it can come across as simultaneously self-deprecating and catty. I mean, sometimes it's true, I can't wear a size 2, but I absolutely can wear a mini skirt. Who's going to stop me?
If I see another woman who's sporting a trend that's not 100% flattering on her, I'm more likely to be impressed she's wearing something she loves and making the effort to be current, than judgmental that her outfit isn't perfect for her body type. I may be going through life blissfully unaware of all the judging eyes criticizing my fashion choices, but so long as I'm happy, I really and truly don't care. I probably couldn't have said that 10 or 20 years ago, but now? I have confidence in my own judgment, and if I'm unsure, I'm confident enough to ask for advice.
So, I guess what I'm saying is... if a new look appeals to you, absolutely try it. "Can't" can often be a lie you tell yourself. You've been dressing yourself long enough that you'll know if it's right. And if you think your mind might be playing tricks on you, that's what we're here for.