Memorial Day signals shorts season, and that means you’ve probably planned a shorts shopping excursion. Like most women, you’re probably awaiting this outing with the same enthusiasm you muster for major dental work.

That’s because shorts are incredibly difficult to fit. They include three of the same tough-to-fit points as full-length pants: waistband, hips and rise. They also offer far less material, which forces us to pit coverage preferences against figure flattery priorities. Finally, unbeknown to many irritated shoppers, they fit differently than most full-length pants, which may lead to size tinkering.

Know going in that no matter how old you are, how you’re shaped or what style you like, it will be challenging to find a great fit that feels fabulous right off the rack.

But there’s hope! Read on for tips to track down shorts that make you look great without sacrificing comfort. 

How shorts should feel

Because of how they’re designed and how they move with our bodies, shorts in your typical pant size may dig mercilessly into your midsection. Ignore the size tag, and try a size or two up to avoid uncomfortable squeezing and undesirable muffin top. Unless you are short-waisted or carry your weight in such a way that a low rise looks and feels best, try high- and midrise styles. Yes, high-rise shorts may momentarily recall Farrah Fawcett in her prime, but as long as you wear them with an untucked top, no one will be the wiser.

In the fitting room, sit down and stand up in every pair you’ve selected. All shorts will ride up your thighs a smidgen when you sit down, but if any pairs shrink back into bikini-bottom shape, you’ll be miserable. Experiment with inseam lengths and heavier fabrics for a less ride-prone fit. If shorts cut into your thighs when you’re seated, try a style with wider leg openings.

Also walk around in any potential new shorts. A bit of bunching is natural unless the leg openings are wide and your thighs are quite slim, but excessive bunching is irritating and unsightly. Products such as Bandelettes (lacy garters that reduce friction) and No Riders (iron-on patches and inseam stays) can help if this is a problem you face with all shorts. But if it only happens with certain styles, try wider legs or heavier materials. 

How shorts should look

Comfort is key, but you also want a pair of shorts that work with your figure and personal style. Focus on fit first, but then shop around for designs that make you look your beautiful best.

Shorts are such a small garment, but certain cuts can get alarmingly voluminous. Wider leg openings can minimize bunching when you walk, but too much volume can throw off your proportions. You don’t want your legs to look like clappers inside of shorts-shaped bells. Ideally, shorts should stand away from your thighs no more than about 2 inches on either side.

Length is very much down to personal preference. Some of us prefer a sassy shorter short, while others are comfortable only with more coverage. But if you’re looking for a flexible guideline, here it is: Four fingers’ width above the top of your kneecap is a good length on most figures, including those with long waists and shorter legs. If you prefer something shorter, a 4- or 5-inch inseam is short without being super-revealing. (It may make me sound stodgy, but butt cheeks peeking out the back of 3-inch inseams alarm me. I prefer the look of something just a bit longer.)

Like bunching, some wrinkling around the crotch area is unavoidable, but certain fibers are more whisker-prone than others. In many cases, sturdy denim or twill will wrinkle a bit less than floaty rayon or linen.

Finally, if you carry weight in your midsection and find that many styles of shorts add bulk to your belly, try non-fly or pull-on styles. They won’t bulge as much as button-close and zipper-fly styles, but instead sit flat against your middle. And again, with an untucked shirt, no one knows your shorts-related secret. 

Fitting workarounds

Tried all these suggestions and still are unable to find a pair that wows? Don’t despair. For starters, consider having nearly perfect shorts tailored. I know it may seem like a frivolous expense, but so is buying three new pairs of shorts each year and never wearing any of them. I bought a pair of Bermudas that fit perfectly in the waist and had them shortened to my preferred length. And I’m much happier now.

You can certainly try making your own shorts from pants that fit well in the waist and butt. Jeans or chinos with busted knees or raggedy seams can be cut off to shorts length — but beware. Because shorts are generally wider in the thigh than full-length pants, this doesn’t always work.

Finally, shorts don’t change much, stylistically speaking, so you can thrift for them. A five-year-old pair bought secondhand is unlikely to look dated, and by buying used, you save money and give yourself access to a wider pool of choices than the mall can offer you. Try on as many pairs as you have the patience for, including styles and lengths you might not ordinarily wear. You may find some surprise winners.

Got more shorts-related questions? I’d love to help. Reach out to tellus@startribune with any shopping, fashion or fit conundrum. 

Sally McGraw is the author of Already Pretty, a daily blog about the intersection of style and body image.