Dating Don’ts: What Not to Wear on a First Date


(Original story published on Monday August 17th, 2015 on

We’re all for testing out the latest trends, but when it comes to dating, sometimes it’s best to leave the man-repelling get-up for girls’ night out… well, assuming you want a second date.

To help you along on your journey to find love, we’re highlighting the 10 fashion items to steer clear of on a first date. But because we would never want you to sacrifice your enthusiastic sense of style for any man, we’re following the “don’ts” with tips on how to get your style across in the most chic, sophisticated way.

And if he still doesn’t call? Next!

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Don’t overdo it
Hoop earrings, bright and tight dresses, and six-inch heels. This isn’t Vegas. And showing up looking like a Real Housewife will only make him think you tried too hard.

dating donts aritzia dress
Try a more conservative shape
But, there’s no need to ditch your tight numbers altogether. Try Wilfred Free’s Nobis Dress ($110) which comes in a form-hugging wool and yak blend which is equal parts sultry and sophisticated.

dating donts heels
Don’t wear uncomfortable heels
Those Atwoods you blew your rent money on? Fabulous! But anyone who sees you trotting along in them can basically feel your pain. Leave the uncomfortable heels you can hardly walk in at home. Because after all, if said love interest wants to end the date with a walk along the lake (erm, or a late night pizza slice) you don’t want your feet holding you back.

dating donts club monaco heels
Try a chunky heel
There’s no need to ditch the heels altogether. Just go for an option with a comfortable thick leather band like a mule, and boasts a stacked chunky heel. Our pick? Club Monaco’s Ava Snake-Effect Sandal ($298).

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Don’t show too much cleavage AND too much leg

There’s no need to reveal too much– in fact, haven’t our mothers always told us to leave our dates wanting more? Choose to either wear a low-cut piece or a super length-lengthening number for the best look.

dating donts hm dress
Try a low-cut dress that’s cropped at the neck
H&M’s Jacquard-weave dress($70) is a standout pick for looking elegant and intriguing.

Don’t go overboard on volume
Loose, relaxed clothing can all too easily come off as sloppy and unflattering. Show off your favourite feature–legs, arms, waist, shoulders–to avoid looking swallowed up in your clothing.

dating donts miu miu belt
Try a waist-cinching belt
Have a favourite flowy number? Add a skinny belt, like Miu Miu’s Skinny Leather Belt ($290) to define your waist and show off your figure.

Don’t wear flip flops
This is one of those pieces that expands past the dating don’ts list, and more into the every day don’ts list. Vogue editors agree: if there’s one wardrobe piece that’s a total no-no, it’s the flip-flop. Unless you’re on a sandy beach for a tropical vacay, get those heel-smacking sandals out of here.

dating donts jcrew sandal
Try a simple leather sandal
Even easier and more comfortable than flip-flops are sandals boasting a single band or two across the toes. We love J.Crew’s Cyprus Sandals (were $99, now $63) which come in three different colours. They may not be the rainbow selection you’re used to in the flip-flop department, but we guarantee they’ll go with everything in your wardrobe.

dating donts leggings
Don’t wear loungewear
Those clothes you wear when you’re lounging around your home? They aren’t exactly date material. Show up to meet your match having made zero effort, and he’ll think you’re not taking the date seriously.

dating donts ted baker leggings
Don’t wear loungewear
Those clothes you wear when you’re lounging around your home? They aren’t exactly date material. Show up to meet your match having made zero effort, and he’ll think you’re not taking the date seriously.

Don’t be a trend victim
So you read Vogue,, and every other fashion website out there. You know the hottest designers, the coolest pieces to own, and the biggest trends of the season. But that doesn’t necessarily mean you should try all the latest trends.

dating donts zara kimono
Try wearing only one trendy piece at a time
We love the darling grandma-inspired looks at Gucci but sporting the trend entirely is a surefire way to scare off your date. Instead, pick a trendy piece or two to rock without going overboard. Try Zara’s Printed Kimono ($70) with a blouse, jeans and chunky heels for the perfect balance.

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Don’t be a bunch of hipster clichés
You’re cool and ahead of the trends, but wearing too many “trendy” pieces at once can make you look like you’re playing dress-up. Pick one or two of your favourite avant garde pieces, and keep the rest of the look simple.

dating donts prada glasses
Try wearing just a few eclectic pieces
Your statement-making glasses lend your look a cool factor as is. Stick with a great pair (like Prada’s PR 14RV Journal (for $415 at Lenscrafters) and a few straight-forward numbers.

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Don’t go boho overkill
We know, we know: You love your summer music fests. But that doesn’t mean you need to show up on your date looking like a full-out flower child. Leave the crochet vest, flower headband, and fringe bag out of the picture.

dating donts anthro clutch
Try a single bohemian accessory
Of course, we’re not saying you need to abandon your bohemian-inspired style completely. Opt for a great piece or two (like Anthropologie’s Chandelier Beaded Pouch for $68) and pair it with an LBD or just jeans and a tee.

Street Style in Madrid
Don’t be #basic
You say you’re not like other girls, but why would he think that if you’re donning exactly what everyone else has? Ditch the over-played pieces to avoid looking #basic.

dating donts tai necklace
Try less trends, more personal preference
Swap out your statement necklace for a more delicate option, like Tai’s Freshwater Cultured Pearl Necklace ($73).

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