Top 5: Ways to Wear Shorts

I LOVE Summer. I’m a “the-hotter-the-better” kind of girl. Give me 35° degrees over 0° degrees any day, any time, any where…so bring it on Summer, I’m ready for you!

I will admit though, dressing for the heat can be a little challenging. One of my tricks for staying cool when it’s hot outside? SHORTS! Shocking I know 🙂 but shorts are often overlooked in favour of the ever-popular sundress or written off as either too casual or too “young”.

I get it. Shorts can be tricky. Most women think they don’t look good in shorts. Or are worried that they’ll ride up places where they shouldn’t, but honestly the right pair of shorts can hide a myriad of sins and are so much better suited to the heat than a dress (good bye thigh chafing).

It’s all about finding the right length, cut and fabric for your body and then styling them so that you look effortlessly chic. Easy right? Don’t worry, it actually is! Lucky for us, everything from long and drapey, to long and straight, to short and drapey, to short and fitted are in style right now.

Ok, so first of all, let’s talk length. Self-conscious about your legs? Find shorts that end at the narrowest part of your thigh and avoid a cuff which can add bulk. Stay at least 1″ up from the top of your knee cap, anything lower can make your knee look pudgy. Look for a pair of shorts that aren’t super tight through the leg. By leaving a little wiggle room between your legs and your shorts, you’ll feel that much slimmer and won’t have to worry about pesky cellulite showing through or squishing out under you shorts. Mid-length shorts (a 7″ to 8″ inseam) are generally flattering on most people. On the shorter side? Go as short as you dare to help lengthen your legs (3″ to 5″ inseam). Taller? Lucky you, you can wear anything from 3″ to 10″.

Are you pear shaped? Grab a pair of high-waisted shorts that draw attention to your narrowest part (your waist). Opt for something looser through the hips and legs like a pair of paperbag-waist shorts in whatever length you feel comfortable in (5″ to 8″). I know the tendency here is to reach for a pair of flat-fronted Bermuda shorts, which is totally fine, just make sure they’re high-waisted and looser in the leg otherwise you might end up looking boxy. Stay away from pockets or any other sort of embellishments on your hips and thighs. The goal here is to showcase your waist.

All you apple-shaped girls out there, reach for a pair of looser-fitting boyfriend or girlfriend shorts which will add a bit more volume to your bottom-half and create some balance.  Stay away from low-rise and anything too short or anything too long (a 5″ to 6″ inseam is your sweet-spot). Pockets, pleats…anything that adds a bit of bulk to your hips and helps give you more of a waist…are your friends. A-line, flared or paperbag-waist shorts in drapey fabrics are also great for you as they can help to give you a waist and balance out your top half.


Shorts are a must-have for outings where you'll be sitting on a cold chair or barstool for a looooong time (like brunch with good friends) because they keep parts that should be covered, covered...enough said. Plus paperbag-waist shorts are loose fitting, perfect for big meals! Make sure you tuck in your shirt with paperbag-waist shorts so that you look polished not sloppy.

Paperbag-Waist Shorts available at RW&CO. $69.90*; Skinny Belt available at RW&CO. $39.90*; Button-Down Shirt available at H&M $14.99*; Cuff Bracelet available at Le Chateau $25*; Suede Mules available at Le Chateau $99.95*.


To showcase Alicia's tiny waist and give her some extra length, we went with high-waisted short shorts but you could easily recreate this look with a pair of mid-length denim shorts. A long blazer worn open is a great way to minimize a fuller bottom half while still highlighting your waistline.

Denim Shorts available at H&M $*; Relaxed-Fit Blazer available at H&M $*; Knit Tank available at H&M $*; Jordyn G Necklace available at Hudson's Bay $22*; Straw Tote Bag available at H&M $29.99*; Sam Edelman Espadrilles available at Hudson's Bay $125*.

Sunday Funday

When looking for white shorts, denim is a great option. The thicker material ensures that they aren't see-through. Avoid the urge to go super-tight (especially if you're opting for a short pair). Pair with a looser fitting top to keep it casual and stylish.

Denim Cut-Offs available at H&M $34.99*; Smoked Top Available at H&M $29.99*; Etereo Statement Earrings available at Hudson's Bay $22*; Huglag Block-Heel Sandals available at Aldo $90*.

Boardroom Babe

If you're one of those people that are lucky enough to be able to wear shorts to work - DO IT! I would much rather sit at my desk in a pair of shorts than in a mini skirt - wouldn't you? These high-waisted, longish, trouser-like shorts are perfect for work, especially when paired with an oversized blazer. The tie-waist helps to emphasize Alicia's waist while the looser fitting leg creates a long and streamlined silhouette.

Paperbag-Waist Shorts available at H&M $34.99*; Camisole available at H&M $19.99*; Oversized Blazer available at H&M $39.99*; Necklace available at H&M $6.99*; Town Shoes Danielle Strappy Sandals available at Town Shoes $119*.


I know I already featured a pair of denim shorts but I don't think one pair is enough. Everybody needs a pair of distressed, high-waisted shorts for more casual outfits. Look for a pair that's looser in the legs in whatever length your prefer.

Levis Wedgie Distressed Shorts available at Plenty $90*; Wave Wanderer One-Piece Swimsuit available at lululemon athletica $128*; Oversized Shirt available at H&M $29.99*; Rose Gold Sunglasses available at RW&CO. $25*; Vince Camuto Rentin Sandals available at Town Shoes $130*.

How do you style your shorts?

*Prices quoted are regular prices, before taxes. Price and availability are subject to change. Please see stores for details.