Summer is the best season—frosty cocktails by the pool and
cute swimsuits at the beach—but warm weather also ushers in a few season-specific fashion dilemmas (hint: crop tops and cubicles rarely mix). We consulted Joelle Litt, a Toronto fashion stylist with Judy Inc., for her expert tips on making it to Labour Day without committing a single summer fashion
faux pas.

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Summer fashion mistake #1: Flip-flops

Thinking of wearing flip-flops everyday? Think again! "Flip-flops are fine if you’re at the beach or cottage, but not for everyday, and certainly not with every outfit,” explains Litt. “They can look sloppy and generic. With so many stylish, comfy shoe options available, you can really have fun and pick which shoe style suits your outfit and your destination."
Instead of flip-flops, opt for fashionable sneakers, cute flats or pretty wedges.

Summer fashion mistake #2: Mismatched sunnies

"Yes, sporty sunglasses are a thing right now. No, they don’t pair well with every look," Litt says. "It’s great to keep up with trends, but the fashion mistake is forgetting about the classic styles which add polish to professional attire and more formal looks."
OTT sunglasses, cat-eye shades and aviators are best for music festivals and outdoor events, while oversized, round and rectangular sunglasses work everywhere else.

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Summer fashion mistake #3: Super short crop tops

The crop top is a summer fashion essential, but save it for the beach or cottage. "The office is not the place for crop tops, unless you are a bartender or a celebrity," says Litt. "A great way to incorporate the crop top is to pair it with a light summer blouse. Do up the lower buttons so that you show a glimpse of your crop top when you move while maintaining that put-together look.”

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Summer fashion mistake #4: Too-high heels

Don’t be one of those subway riders stumbling for a seat in a
pair of pumps that are too big. "How are you enjoying yourself when you can’t walk in your shoes?" asks Litt. "To fix this fashion mistake, visit a few different shoe stores and walk around in as many pairs as you can to find your best fit. You will quickly see a difference in brands, fabrics and materials." Select your perfect shoe size and stick to it, even if that coveted pair of Manolos comes on sale two sizes too large.

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Summer fashion mistake #5: Leggings as pants

This fashion mistake needs little introduction: leggings are leggings; leggings are
not pants. "Unless you’re coming from or going to the gym, leggings can look tasteless," says Litt. To work the body-con look this summer, Litt recommends buying a slightly over-the-knee bandage dress: “In the workplace, toss a light tailored jacket over top.”

Summer fashion mistake #6: Going too sheer

"Here is where it gets complicated," warns Litt. "When we’re getting dressed in the morning, we don’t always realize just how sheer something might be.” The key to wearing the
sheer trend is layering-up with a light jacket or vest. "For the beach or cottage, go sheer and have fun—no layers necessary. Anywhere else, light layering is a must."

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Summer fashion mistake #7: Pyjama dressing

We’re all for relaxing and catching a few extra zzzs this summer, but there is a difference between wearing the pyjama-dressing trend and wearing your lingerie outside the boudoir. "The fashion mistake here is making pyjama dressing look too casual—there is a fine line between lazy and chic," says Litt. "Dress up your pyjama look by wearing a slip dress paired with a silk blouse or lace camisole, then add accessories like a
fabulous bag and a fabulous shoe.” Sweet summer dreams, here you come.

Read more:
What to wear to work this summer
100 plus best summer fashion accessories
The summer fashion pieces we can’t wait to buy
How to wear the jumpsuit this summer