4 Hair and Makeup Dares to Try in 2015

Everyone has a beauty fantasy, right? Yours may not be appearing spray tanned in the buff in a national magazine—but maybe it's swapping long hair for a pixie or leaving your makeup comfort zone. Because we firmly believe there are some risks worth taking, we persuaded four women to embrace a look that scared them. For expert guidance (and hand-holding), we gathered an all-star team: hairstylist Nathaniel Hawkins, makeup artist Troy Surratt and spray tanner Natalie Cupid-Riley. Let the adventures begin!

Ruthie Alcaide

(Age 37)

Her Fear Factor: Trying a short haircut

What's Holding Her Back: "I don't want to look like a boy! And my hair is naturally wavy, so I'm worried that it will be poufy and uncontrollable. Also, I don't know if I have the face for cropped hair. My features are kind of flat."

The Leap of Faith: Having 12 inches of hair hacked off isn't for the faint of heart. To put Ruthie's mind at ease, Nathaniel methodically addresses each of her concerns. And to make sure she gets the feminine result she's hoping for, he cuts her hair at different lengths throughout. ("If it were the same all over, it would look harsh," he says.) To accommodate Ruthie's wavy texture and prevent fullness, he cuts her hair very short on the sides. He also creates sweeping bangs to cover her forehead and make her face look less elongated. Styling is low fuss: Nathaniel applies an oil serum to Ruthie's wet hair before blow-drying to soften it and add shine. Once her hair is dry, he works through a texturizing cream to play up her layers. A couple of blasts of a root-boosting spray create lift and piecey-ness. And that foot of extra hair? It was donated to make wigs for children who have lost their hair.

The Verdict: "Why was I so afraid, and why did I wait so long? This is much more me!"

Most important when you get a cropped cut: Find the style to flatter your face shape.

Oval (Left)
This face shape can handle any style, like this super-short traditional pixie.

Round (Middle)
To lengthen and slim your face, aim for a strong side part or add volume at the crown.

Square (Right)
De-emphasizing the sides of the face, from the crown to the jaw, is the name of the game. Tucking your hair behind your ear creates a shadow on the jawline, softening it. Tousled bangs minimize a broad forehead.

(Age 29)

Her Fear Factor: Spray tanning her pale skin

What's Holding Her Back: "I'm naturally super-fair, thanks to my Irish heritage. My main concern: Any tan is going to scream 'fake.' And I don't want it to be splotchy or uneven."

The Leap of Faith: Looking natural is about finding the right shade for your skin tone, Natalie says. Too-deep color is a sure sign your glow is faux. She suggests taking a bottle of foundation in your ideal shade to your appointment, so the technician can match it exactly. For streak prevention, pretanning prep is essential; you need a smooth canvas to absorb the product evenly. Natalie advises Ali to exfoliate top to bottom before the treatment with a loofah or a washcloth. "Avoid oil-based scrubs, as they can leave a residue that blocks the tanner from penetrating," she says. This last point is so important that Natalie tells Ali she should come to her session wearing no moisturizer, makeup, deodorant, or perfume—all can make the color set irregularly. "And don't try to create a 'base' in advance by using a body lotion that contains self-tanner. Not all self-tanners work well together."

The Verdict: "It's so great to glow! My hair looks blonder, and my teeth seem whiter," Ali says. "I exercise daily, but I've never seen any muscle definition before. My abs are much more pronounced!"

Technical Support

According to Natalie Cupid-Riley, owner of Glow the Spray Bar at Roman K Salon in NYC, the average life-span of a faux tan is fve to ten days. Maintain yours with these four tips:

After tanner is applied, don’t shower or work up a sweat for eight hours (the time it takes for the tanner to fully develop). For your first shower, simply rinse; avoid soap and shampoo, which can remove too much color.

Choose a nongreasy body lotion, as residue can lift the color, making your tan rub of on clothing.

Wash in lukewarm water—not hot, which dries out the skin, causing the color to fade.

Avoid heavily perfumed products, which are also dehydrating. nix anything with an exfoliant, such as an alpha or beta hydroxy acid. You don't want to slough of your tan.

Dress, Shoshanna, $440. From top: Geometric bracelet, Lisa Freede. Glitter bracelet, Fornash. Thin bangle, Jules Smith.

(Age 24)

Her Fear Factor: Wearing a dramatic cat eye

What's Holding Her Back: "Whenever I try eyeliner, the results look completely uneven. One side is always thicker than the other. And I can't seem to manage to draw a straight line, so I just give up."

The Leap of Faith: Troy shows Winter she doesn't need a steady hand to get a flawless cat eye. The key to a smooth line is not to draw it in a single swipe. His three-step method for the perfect cat eye: 1. Use liquid liner to create the tail first, starting from the outside end point and drawing down to the corner of the eye. (You can lay a Post-it along this outer edge as a guide for where to place the liner and to make sure the flicks are even.) 2. Draw a line from the inner eye corner to the inner edge of the iris. 3. Connect the lines. "If you make a mistake, use a little makeup remover on a pointy cotton swab to clean it up," Troy says. Another of his tricks is to lay a mirror flat on a table and look down into it while applying liner, "so it's easier to see what you're doing," he says. Liquid liner glides across the lashline much easier this way since the brush rests on top of the lashes.

The Verdict: "I can do this! I love the look for nights out. Liquid liner is easier to apply than the pencil I've been using, especially now that I know to do it in stages."

Technical Support

Got your technique down? Here’s the secret to making sure your artistry stays put.

Step 1: Apply a thin layer of concealer or primer on lids.

Step 2: Dust a light coating of translucent powder or nude eyeshadow on top.

Why This Works: These products absorb oil, which can cause eyeliner to break down. They also keep your liner from smearing. The base is especially helpful if you have oily lids or deep-set eyes.

Sweater, Magaschoni, $298. Hat, Preston & Olivia. Earrings, Melinda Maria.

(Age 41)

Her Fear Factor: Leaving the house without heavy makeup

What's Holding Her Back: "I like looking polished and 'done.' In my job as a physical therapist, I have to wear a golf shirt, khakis and sneakers. Makeup is the only way for me to feel feminine and attractive, but I wish I could try more options."

The Leap of Faith: Troy tells Dawn the solution is less about giving up her beloved cosmetics and more about changing her color palette. "Dawn was wearing a lot of black around her eyes, which can be harsh," Troy says. "Brown still gives you definition, but it's much softer." By keeping her lids light and bright with champagne shadow, Troy creates a backdrop to show off Dawn's luxurious lashes. For her lips and cheeks, he chooses tones of peach, a warm, flattering shade. He suggests either using a light hand on the eyes, lips and cheeks (as he does with Dawn) or enhancing one feature and letting the others play backup: "The easiest way to look overdone is to wear a strong eye, a bold lip and a sculpted cheek all at once."

The Verdict: "I still feel pretty without the heavy application. And my skin has a glow. Plus, my fine lines are covered. I love this!"

Dress, BCBGMAXAZRIA, $448. Circle necklace, Kismet by Milka. V necklace, Mary Louise Designs.

All you need are seven products to get a pulled-together but natural look.

1. Sheer, Tinted Lip Balm (Maybelline New York Baby Lips)

2. Mascara (L’OréaL Paris Voluminous Butterfly Intenza Waterproof Mascara)

3. Spoolie Brush for Brows (Jane Iredale Deluxe Spoolie Brush)

4. Eyelash Curler (Surratt Relevée Lash Curler)

5. Concealer (Clé De Peau Beauté Concealer)

6. Highlighter (YSL Touche Éclat)

7. Loose Powder (Neutrogena Mineral Sheers Loose Powder Foundation)