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If you can, always have a shopping buddy. This person can be a friend, family member, or significant other. When you try on different pairs of shorts, ask him or her if you look good in them.  It's important to get someone else's perspective when shopping, since too often people are their own worst critics. Especially if your self-confidence is low, you will see "flaws" that nobody else would notice. Make sure your buddy is someone you can trust to be honest. If a pair of shorts is legitimately unflattering, you want your shopping buddy to be honest and tell you. Many people are afraid of offending people and won't give good advice in these situations. On the other hand, don't go shopping with someone who is hypercritical. If your buddy never has a good word to say, you may feel too self-conscious to buy shorts at all. This may seem like a given, but it's the most important part of finding shorts that make you look good. Don't worry so much about fashion trends or looking perfect. Dress how you want to dress.  If you have issues with clothing texture, be sure to look for shorts made of materials you find comfortable. You might find the chicest, most flattering pair of shorts, but if you think they're ugly and uncomfortable it will be difficult to look confident. Self-confidence is essential for looking your best. Shorts are generally for beating the heat, but different types of shorts are best worn in the appropriate situation. Think about what you want to do in your shorts and how you want to look while doing it. Questions you should ask while shopping are:  Do you want to look sexy, casual, or both? There are some shorts that can work as part of a dinner outfit, and there are shorts that are better suited to wear around the house. There are different lengths of shorts from sexy ones meant to show off your butt to modest shorts that reach past your knees. Are you looking for athletic shorts? If so, for which activities? The best shorts for playing basketball aren't the same as shorts designed for running. Just like other types of clothing, different styles of shorts can exaggerate or draw attention away from certain body features.  To accentuate curves, wear shorts that are longer  and/or have an A-line silhouette.. To make your legs look longer or to look taller, wear shorter shorts and/or ones with higher waists.  Low-to-midrise cuts will make your torso look longer and your legs shorter.  Wear "skinny" or fitted-cut shorts if you have thin legs that you would like to look fuller. Likewise, if you legs are on the thick side, wider cuts will flatter them more. This step is extra important if you didn't bring a shopping buddy. Like all types of clothing, you look best in clothes that fit your body right. A perfect fit is one that doesn't feel restrictive while also not being too baggy. Some fitting issues you should watch out for with shorts include:   Muffin tops. When you wear shorts that have waistband that's too small, your tummy will bulge out in a way that many people find unappealing. Anyone, even thin people, can get a muffin top when wearing too-small shorts.  Sliding off. This is caused by a too-wide waistband. Your shorts should only hang low if that's your style.  Riding up. For a lot of people, especially women, even the best-fitting pair of shorts may ride up over time. However, if you find a pair riding up right after you've put them on, just think how uncomfortable they'll get later in the day. If this happens, look for a looser style with a wider leg.
Take another person shopping. Look for shorts that you like. Consider the style of shorts that you need. Think about cuts that flatter your body. Buy shorts that fit properly.