I want to wear shorts but they always look awful on me! Ask The Kit

Shop With The Kit is the personal shopper column that will solve your style dilemmas. Every month, Julianne Costigan, The Kit‘s stylist-at-large and author of the shopping resource The Digital Style Guide answers your questions, giving you real solutions for building a functional, stylish wardrobe. What should I pack for a vacation? How can I dress well at my new job? How do I establish my very own “uniform?” Send your Qs to [email protected]

“I want to wear shorts, but I have so much trouble finding pairs that are flattering on my body. I’m also not sure how to put them into outfits that feel sophisticated. Can you help?” — Esther, Ottawa

Shorts are supposed to be a fun and freeing wardrobe option for summer and yet, many of my clients and friends come to me each year complaining about the struggle to find, buy, fit in or wear them. From confusion around sizing and styling to navigating wrinkles and feeling confident while showing some leg, shorts can definitely be daunting.

When you do find the perfect shorts, however, they’re comfortable and elongating and allow you to move around carefree (unlike a short dress or skirt), making them worth the effort.

To help clear up the confusion, here are my answers to the most common shorts questions I hear.

The incredible thing about the human body is that we all come in different shapes and sizes, it’s what makes us special! In a perfect world, we would all have custom-made clothes that fit flawlessly, but budget and time stand in our way here. Instead, the best way to find a great fit is to understand your general shape and have a sense of what silhouettes will usually work best on you.

There are five shapes that a majority of women can relate to; A, V, O, H, and 8. Keep in mind that these shapes don’t consider height and weight, which will be additional factors in the pieces you buy. Here’s where to start with short styles for each shape:

A Shape (Wider hips than shoulders)

Stick with a slimmer-fitting style and look for fabric with stretch to avoid waist gaps.

V Shape (Broader shoulders than hips)

Go with A-line or wide-leg shorts to balance your shoulders.

O Shape (Wider torso than shoulders and hips)

Try a midrise and mid-length (midthigh) and avoid pleats or volume at the top of the shorts.

H Shape (Straighter shape through the waist from shoulder to hip):

Opt for wide-leg shorts that offer waist definition via a belt or pleats. Stay away from lowrise.

8 Shape (Smaller torso than shoulder and hip, which are even in width):

Choose a high-waist style with a snug-fitting waistband.

Comfort is key in terms of both feeling and looking your best in well-fitting shorts.

A few signs that shorts are fitting poorly: excessive gaps at the waist; if there are red marks or indents left behind when you take them off; and if they feel uncomfortably tight around the thigh, waist or bum (a good test for this is to sit and move around in your shorts for a few hours to see if they stretch out at all).

When looking for the right size of shorts, remember that every store is different and you won’t be the same size at each. My advice is to always take a few sizes of any one style into the change room so you can compare and find which is the most comfortable and flattering.

If you’re someone who always has a gap in the back of their shorts but sizing down means they’re too tight at the thigh, buy the pair with the waist gap and get the waist tailored. Or look for a pair made with a stretchier fabric that will hug your shape better (anything with over 2% elastane or spandex will be stretchy.) As an alternative, buy a pair with an adjustable belt or stretchy waistband.

If you are someone who finds their shorts are always riding up, chances are you need to size up and/or go with a longer inseam. Inseam lengths will be a big part of finding a fit you enjoy wearing, so know the difference between them. Three inch inseam = your daisy dukes, 5 inch = upper thigh, 7 inch = midthigh, 9 inch=bermuda short. Choose the length most suitable for your lifestyle and comfort level.

Shorts with a pattern or texture, especially in linen or cotton fabrics, can mask pesky wrinkles or underwear lines. Wrinkles are completely natural and sometimes unavoidable, but a quick swipe with a hand-held steamer is a great option.

If you notice underwear lines, dark-coloured shorts will hide them but my advice would be to switch up your underwear and invest in seamless styles that won’t show through any bottoms. My favourite is the Spanx high-waisted Everyday Shaping Thong.

Chafing can cause so much discomfort. To avoid it, stay away from short shorts and go for a longer style that will cover the area that typically bothers you. You can also use an anti-chafe stick like Megababe Thigh Rescue, which you can use and reapply throughout the day.

Veins, thigh or calf size and stretch marks have held too many women back from wearing shorts for too long. I strongly believe in using clothes to highlight our favourite parts of ourselves rather than using them to hide the parts we don’t. Put on a thick layer of confidence and shorts you love, and you’ll forget about your legs. If you’re not ready to do that, just go with capri pants in a light fabric instead.

In cooler months, you can try layering a pair of tights underneath your shorts — leather shorts with black nylons and tall boots can be very chic.

Jorts, a.k.a. jean-shorts, have been topping the trend charts thanks to celebrities like Hailey Beiber, Regina King, Gigi Hadid and Gwyneth Paltrow. The Bermuda length is especially popular and can be seen in fabrics from denim and cargo to light, loose, flowy fabrics. A few of my clients who are petite have come to me wanting longer Bermuda shorts but worrying they won’t flatter a shorter leg. My solution? A higher-rise short with a shorter inseam. This will create the same look but the length is redirected to the higher waist rather than the longer leg.

Another trend worth jumping on is tailored shorts. The signature trouser-style waistband is classic and will add an elevated touch to every look. Boldly-patterned pieces, sports shorts and short shorts are also on the trend radar.

Similar to jeans or great trousers, shorts have endless styling possibilities. A few key pieces that will make putting a shorts outfit together simple are a black or navy oversized blazer, a cami or white t-shirt, a white button-up and a striped crewneck knit. With these few pieces, you can wear any pair of shorts effortlessly. Tuck in a button-up and add a blazer and ballet flats for work. Tie a sweater over the button-up and swap to a sneaker for the weekend. A white tee can work with any shorts you have — add some layered jewelry or wear an open button-up on top to complete the outfit.

Now that you’re a shorts styling and fitting expert, I’ve put together a few looks to help you get started on wearing them to work, on the weekend or on a night out.

The Look: Achieve a sophisticated warm-weather officewear look with a trendy trouser-style short. This cuffed-hem version from Aritzia is lightweight, not see-through and will quickly become an essential. Take shorts from the weekend to work by pairing them with traditional officewear items like a classic button-up and structured blazer. Finish the look with a ballet flat or loafer and structured tote.

Aritzia shorts, $98, aritzia.com SHOP HERE

The Look: Dress up shorts by going with a flowy, patterned style and pairing them with a billowing blouse and heels (the combination of shorts and heels is extremely elongating). Choose a belted short like this pair to add a touch of sophistication, waist definition and hardware.

Mango shorts, $60, thebay.com SHOP HERE

The Look: Celeb-approved denim shorts are perfect for any weekend adventure. Have old jeans that are too short or the wrong style at the hem? They are a perfect candidate for DIY Bermuda jorts. Simply measure and mark them to the length you want, grab a pair of scissors and get to repurposing. You could have a tailor finish the ends or just wear them raw.

Gap shorts, $70, gap.com SHOP HERE

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