Perhaps you could use a break. I know we're ready. And thankfully now is the perfect time to get out of town. Call it spring break, or merely a long weekend trip to reset and recharge, but book something now and then start packing. One fool-proof strategy to look and feel your best when on the road is to “underpack”—only take your favorites. You're happy to wear and re-wear them, mixing and matching to get the most out of just a few pieces. This way, you end up with a lighter suitcase and room for souvenirs.

Our favorite travel look these days consists of a lightweight vintage-inspired jacket, a super-soft cropped tee and a pair of relaxed pants that are easy to dress up and down. Constructed from garment-dyed mid-weight cotton twill, Alex Mill's popular pleated chinos in this rich olive colorway can easily be worn every day for a week with no problems. Round things out with handsome shades (that are so cheap you won't be bummed if you lose them) and a roomy tote cut from nearly indestructible leather.