Here's a question: What happened with the Apple Watch? Yes, it's profitable -- but it's not ubiquitous. Some have touted the relative failure of the Apple Watch as the first dent in a corporation without their resident creative genius helming the ship. The wearable market is stirring, but is nowhere near the omnipresent force of cell phones. Maybe that's due to change soon.
No matter how your life changes, your style will always be yours. So why would you ever wear something that didn't make you feel good? Style is what you make it. It's personal and it should reflect who you are. So if you're not feeling that pair of Uggs or just don't feel comfortable in skinny jeans -- don't wear them.