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How to Match Shoes With Your Outfit To put your best foot forward in the right pair of shoes every time, just follow the tips below. Steps: 1. Pair a long skirt with ankle- or knee-high boots, flat shoes, ballet slippers or backless slide-ons. 2. Wear conservative pumps of medium height with skirts for work. A rounded or square toe and a stacked or slightly tapered heel look professional. 3. Choose platforms or clunky loafers with some heel with a casual skirt. 4. Don stylish footwear with a dressy skirt. Try high sandals for skirts that graze or just cover the knee, or pointed-toe shoes with Sabrina heels. 5. Zip up some knee-high boots with a miniskirt if you're leggy and bold enough. 6. Ground your jeans or corduroys with boots, chunky-soled shoes or sneakers. 7. Slip on open-toed flats or espadrilles with soft, looser pants such as palazzo pants. 8. Choose oxfords or loafers that are flat or have low to medium heels with business pants. 9. Wear boots with long, dressy pants, or high, strappy sandals with straight, glamorous pants in sleek fabrics. 10. Put on platforms or open-toed mules with capri pants, or nosebleed-high sandals for daring nights out. Tips: Wear shoes with ankle straps only if you have long legs. The straps truncate and shorten the leg. If you're shopping for shoes to match a specific skirt or pair of pants, wear the article of clothing while you shop
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