$150 and $100 (respectively), Giro.com
The draw: Go-to short
These shorts are wildly comfortable. The super-wide waistband made of soft Italian Lycra and the broad, elastic-free leg openings contribute to the superior comfort. The chamois is super supportive without feeling bulky. The all-black color scheme lets you pair these shorts with any jersey in your closet, and Giro offers a 60-day return window to ensure you love them as much as we did. The striped jersey features a slimmer race cut, three large pockets and airy mesh paneling at the back.