Bosses can be comfortable in multiple social environments, and that means wearing clothes that can fit any situation. But how can you add variety if all you wear are hoodies and jeans?
Three easy steps:
1. Buy versatile clothes
Some fashions can work when you're at school, your job, or even at a hip party. Polo shirts, collared button downs, khakis and nice jeans can be worn anywhere, at any time and for any occasion. A casual jacket or has the added value of being both an accessory and keeping you warm, and usually looks better than a sweatshirt.
2. Never throw out clothes
Fashion is cyclical and you never know when something will slip back into style. In addition, if you only buy versatile, timeless threads, they'll never be out of style for long. Five years ago if a girl wore leggings, people thought she was weird, now they're everywhere!
3. Ask loved ones for clothes
No one has your best interests at heart like your friends and family. Ask them for your next birthday (or religious holiday) to get you something that they think you'll look good in, and something that's typically not your style.
I can't tell you how many times I've opened a present, hated the look of it, and only once did I put it on I realize how good it looked. If you're too preppy, new clothes might edge your look. If you're thuggish, a collared shirt might will soften it.
That's not to say that you're supposed to go to a DnB party dressed like a j.crew model, or if you're going to your girlfriend's house, you like you came from a thrash metal concert. But if your look is versatile, you look like you can fit in at all those places.
Live the Boss life, and add variety to your wardrobe. You can't run things if you don't look the part.