With the exception of the most confident and self-assured amongst us, many of us covet out-there, pushing-the-envelope looks, but don’t feel we can pull them off.

Come to think of it, even just applying a
sexy smoky eye or wearing a richly hued lipstick is more than what many of us feel we manage. So how to wrap your head around pulling off a bold look so you can "werk it"? Some words of wisdom from beauty pros on how to develop your beauty backbone.

 Beauty secret 1: Remind yourself that the look is temporary
"Remember, it’s just makeup — it washes off," says Jessica Jara, a makeup artist with Stila Cosmetics.

So don’t stress over it. And in the case of more permanent looks, for example, candy-hued haircolour, look for more temporary choices, such as using Kevin Murphy Color Bugs to give your hair a fun, unexpected, non-committal touch of colour that shampoos out.

Beauty secret 2: Work on one element at a time for an entire bold makeup look
Graphic eyeliner, look-at-me lip colour and long flirty lashes may all come together on the runway and it’s the look you want to try, but if you’re shy and nervous about it, start by trying a single bold feature at a time, says Jara. "Choose one focal point, whether it’s the cheeks or lip, and try that one day," she says, until you’re more at ease with each element of the look.

Beauty secret 3: Consider alternatives that make your bold choice easier for you
Say, for example, you’re swooning over the deep, matte blackberry lip colours that are in this fall. But it’s such a departure for your usual, neutral lip, which you don’t even to reapply as it fades inconspicuously given its natural tone, that you’re reluctant to try the trend.

Anna Nenoiu, a Toronto-base makeup artist with the agency Page One Management, suggests looking a deep plum shade in a lip stain or pigmented lip balm. With their longer staying power, you’ll have to reapply less often, she says, and depending on the one you choose, the intensity may be more sheer, which will help train your eye to seeing you in a purple lip.

Discover another clever bold beauty secret or two on the next page…

Beauty secret 4: Think of your cosmetics collection like a wardrobe

To help get comfortable with the concept of wearing a certain element of a beauty look, Jara suggests thinking of your
cosmetics collection as a wardrobe.

"In your wardrobe, you have your key pieces, the ones you gravitate towards, and then there’s the ways you help make them pop — how you accessorize them, so to speak," she says.

"The key pieces are items you already wear with confidence, and then you layer or add to the outfit to tone down or play them up — think of your cosmetics in the same way."

This may help you feel more at ease with experimenting and getting more daring with certain elements of your makeup.

Beauty secret 5: Make sure your look is cohesive
"If you want to try a look that’s outside fo the box for you, make sure you develop the entire look, one that tells a story," says Johnny Lavoy, celeb hairstylist and consulting hair expert for L’Oreal Paris.

"Don’t just do the hairstyle, for example, just for the sake of doing it — it’ll look costume-y," says Lavoy.

Do your research, from the hair to the clothes and makeup, and even if you can’t afford the actual clothes, for example, use them for inspiration and look for more affordable versions within the same vein, he says.

Beauty secret 6: Focus on what makes you feel great
Consider what you love about your look — maybe you have great skin, or you love your full lips. Focus on playing those up and that’ll make you feel more confident, and that’ll help you feel more at ease at experimenting with another aspect of your makeup, says Jara.

Beauty secret 7: Follow through and do your due diligence
If there’s a look you love, talk to a makeup artist and find out what products you need and how to apply them, says Jara. She points out that you may need to invest in some tools (perhaps there’s a makeup brush you need to complete a certain eye look, for example).

If you truly want the look to turn out right, you may need to put some money into it, she says. "If you don’t use the right tools, you might not be able to replicate the look as well — and you want to set yourself up for success rather than only going halfway about it," says the Toronto-based makeup artist. With the knowledge and tools, the look will look how it should, and you won’t have to fret about it looking wrong.

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