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Ankle boots can go over jeans and under jeans, but there's more to the story. Ankle boots can look amazing with the right outfit, or ankle boots can look, well...dumb. Knowing how to wear ankle boots really starts with your shape and the boots themselves. If you are long and lean, chances are ankle boots work easily for you, regardless of whether you have them under or over your jeans. Shorter women and women with thicker thighs have to work a little harder to pull this look off. Some basic rules will help you find the perfect ankle boot and jean outfit.
Under the Jeans
When your legs are shorter and you want to create the illusion of height, try darker boot-cut jeans and tall, black ankle boots with just the toes peeking out. In this way, you're creating a long line from your legs to your feet. Women with a pear or apple shape can accomplish the same goal by using dark, straight-leg jeans. Make sure the jeans fit like trousers. You want the fabric at the thickest part of your thigh even with the fabric below the knee.
Over the Jeans
Skinny jeans look great tucked into ankle boots when you have long legs and a boyish shape. The same outfit on a shorter, heavier woman will only make her legs look shorter and wider. Tapered legs and skinny jeans create an unfortunate silhouette when your legs are heavy at the top. Your ankles will look like two tiny sticks carrying heavy loads. Stick with a trouser or boot-cut jean, and keep the boots under the jeans. Cuffed jeans and ankle boots are also a poor match. Above all, never leave any skin showing between the boot and your jeans.
Shopping for Boots
Keep some things in mind when shopping for ankle boots to create the best overall effect. If you have a wide bottom, keep the boot simple. Otherwise, you will bring attention to the size of your feet compared to the size of your rear. Add some color up above your waist to draw attention upward. If, on the other hand, you are heavier on top, find a more substantial, heavier boot to give your body some balance. Shorter women should look for shorter ankle boots, especially if you plan on wearing the boots with a skirt or dress. Boots hitting low on the ankle will give your legs more length. If your ankles are small and your thighs wide, pass on ankle boots with wide tops.
Skip the Jeans
You found a spectacular pair of ankle boots and you want to show them off. Your body, however, is short and a bit heavy on the bottom. Covering your boots under jeans is a crime, and putting the boots over the jeans won't flatter your figure. The solution is to skip the jeans, and wear your ankle boots with an empire-waist dress. Shorter ankle boots will elongate your legs. Don't choose a dress with a lot going on in terms of color and pattern. Keep the outfit as simple as possible to keep the look from going over the top.