Once men reach their 40's and 50's, they tend to become stagnant in their style. Being comfortable in your clothing is important, but it shouldn't take precedent.

In middle-age, you're finished experimenting with your style, but you're not finished refining. What you should focus on now is timeless clothing that looks age-appropriate. Ditch the stuff you accumulated throughout your 20's and 30's that gets pushed to the back of your closet. Let's get that space working better for you, right now.