A crew-neck t-shirt and overalls are the kind of a never-failing casual look that you so desperately need when you have zero time to spare. Burgundy leather casual boots will breathe a hint of refinement into an otherwise mostly dressed-down ensemble. As you can see here, it's super easy to look amazing and stay toasty when chillier weather hits, all thanks to combos like this one. Those wondering how to wear cool off-duty dressing as you work your way through your 20s, this combination should answer your question.