Choose clothes that you can layer to accommodate different types of weather and wear from morning to night. Pack an assortment of tank tops, cardigan sweaters and leggings (that you can use as is or under mini skirts or jeans as another layer of warmth).
Select items that you can incorporate into at least three different outfits. For example, wear a white shirt over a colorful tank top as a light jacket, tuck it into a pair of slacks for a nice dinner or pair it with khaki walking shorts for sightseeing. Consult your itinerary to ensure you're only bringing items that suit your planned activities.
Find solid-colored versions of bulky items like sweatshirts that you can use more than once while you're on vacation. Fellow travelers are more likely to remember your bright-red sweater with Mickey Mouse on the front than a plain black one.
Pack accessories like scarves or belts that won't take up much space in your suitcase but can give outfits an entirely different look.
Cut down on the shoes you bring. Consider a pair of plain leather flats that you can wear sightseeing, shopping or out to dinner. Wear the bulkiest pair in your wardrobe (like hiking boots) as you're traveling so you won't have to pack them.