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The biggest challenge I see for girls/women is how to properly rock leggings/tights. It can be tricky but it’s really SO simple. Here are a few tips that will make a big difference.
The real key to leggings is to remember that they are NOT pants! You should wear a top that compliments the fitted shape of the leggings. A shirt that is longer and loose is ideal. Even if you have a top that hits right above the hips or is cropped, if it’s loose and flowey, it will compliment the leggings.

I personally cannot stand the look of leggings and heels. This combination can read a bit tacky. Jeggings however, are a totally different story. Because the weight of the fabric is a lot heavier and most often resemble denim, it’s a bit more flattering to pair jeggings with heels. They are close to skinny jeans, so it’s not as weird looking.
If you have a bootie or a shoe that covers the ankle, you can have a great look.