Speaking from personal experience, you have to start with the basics. Every closet should include blacks, browns, navys, beiges, and whites. Having a go-to pair of black denim, dark-wash navy denim, light-wash denim, and khaki pants will fill out your bottom essentials. From there you add your bolds. Trends fade, so spend your money investing in the basics. When it comes to your bold bottom choices, shop trendy stores for whatever you're craving that season. Right now, I'd suggest red. It's the color of the season, and it looks great on almost everyone. And don't be afraid of pattern! Patterned pants, although less practical for everyday applications, make a fun and exciting statement in the right look. Use these tips to similarly cultivate your tops collection. Great solid button downs, T-shirts, and sweater are perfect for long term use. I find myself buying more and more tops with a trendier style more often, because it's easier to mix-n-match with your great basic bottoms.