For a casual two-night trip, plan outfits around what you’ll actually do and pick one pair of pants that works with both tops. Lay out the complete outfits at home before deciding what goes in the bag.
Pack by activity, then count repeats
Write down the three occasions you expect: the journey, daytime plans and dinner. If both daytime and travel are casual, wear the same bottom with two different tops. Pack a separate outfit only when a reservation, a workout or the weather calls for it. REI’s light-packing guide recommends choosing pieces that do double duty and making sure layers fit together before you leave.
Test your outfits with the shoes you’re taking
Try on your daytime outfit and walk around in your travel shoes. The White/Light Gray Wide-Leg Joggers have an elastic drawstring waist and side pockets. Use the Fieldtime Size Guide to compare their inseam with pants you know clear the ground. For a casual dinner, try a knit top or a button-up you already own.
Bring the layer the forecast calls for
For breezy daytime plans, the Navy/Kashmir Blue Cropped Windbreaker gives you a light outer layer with adjustable drawcords. Try it over both tops before packing. For a cold evening, bring a sweater or fleece too. If steady rain is in the forecast, pack dedicated rainwear.