16 Flattering Haircuts To Try This Winter Before Everyone Else Is Wearing Them

This article was last updated on April 16, 2022

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16 flattering haircuts to try this winter before everyone else is wearing them

Imagine it’s a windy December morning and you’re standing on the sidewalk waiting for the light to turn, the bone-chilling breeze whips across your face, leaving your chapped lips quivering and your hair a tangled mess. Sounds like you should’ve stayed in bed. But now, consider the same day, but you’ve just had a haircut. All of a sudden, the cold air is fresh and crisp, and mother nature is your personal wind turbine, flipping your ends to perfection.

Now, all you need to turn your winter hair into something along the lines of the latter scene — a style you can’t wait to wear out the door and refuse to cover with a beanie — is to schedule a salon appointment. Not sure what cut you’re looking for? Try one of the five chicest, most versatile styles that are poised to be huge in 2019.

Ahead, we’re breaking down the hair trends that are picking up major cool girl traction right now, only to hit fever pitch come the new year. More than just photo inspiration, we have pro style tips and product recommendations for how to rock the cut all winter long. Take this handy guide to your next appointment and prepare for warmer walks to work.

16 flattering haircuts to try this winter before everyone else is wearing them

The Blunt Jawline Bob

The popular fashion-girl cut is only getting shorter in the new year. Sergio Pattirane, stylist at Rob Peetoom salon in Williamsburg, Brooklyn tells us that the cut should fall somewhere between your ears and chin. “Ask your stylist for a straight bob in line with your jawline, shorter at the back, longer at the front, an inch or two below your ears,” he says. “The result is a modern, streamline bob, that can be elevated through styling.”

If your hair is on the finer side, Pattirane recommends thinning out just the ends for a choppy, sexier finish that gives the cut some dimension. You can also add a little dry texturizing spray (Pattirane likes Davines’ option) through the ends for extra definition.

Celebrity stylist Kahh Spence agrees that the bob cut will be even bigger come 2019. “Depending on the cut or angling of the bob, you can achieve a chic style that flatters any face shape,” he explains. “Bobs are universal, and will work all year long — styled curly, pin straight, or with a soft, barely-there wave.”

16 flattering haircuts to try this winter before everyone else is wearing them

The Grown-Out Pixie

If you’re looking to go way shorter — but don’t know what to ask for — consider the en vogue shaggy pixie cut. Erickson Arrunategui, stylist at NYC’s popular Bumble and bumble salon  tells us that 2019 will be the year of the pixie. “All my clients want newness right now, but they also want a cut with a little body,” he explains. “The grown out pixie stye is short and fun and still maintains length to style.”

For pixie cut inspiration, look no further than Kehlani’s super short cut, shaved on the sides with natural definition on top.

On natural hair, a top-heavy pixie cut feels fresh while still maintaining movement and shape. Slicking back the sides adds a cool polished finish.

16 flattering haircuts to try this winter before everyone else is wearing them

The Heavy Mid-Length Lob

For a cut that falls somewhere between short and long, a mid-length lob is the perfect way to stay on-trend. “This cut has seamless layers, if any, to create a look that feels weightier, more structured, and less textured,” Unite stylist Graham Nation explains. “Ask for your length to be between a bob and a mid-length, with a blunt perimeter.”

16 flattering haircuts to try this winter before everyone else is wearing them

If your hair is thin and you’re itching for a little body, Nation recommends talking to your stylist about blending in some soft, interior layers that are very subtle as to maintain the strong shape. Before a blowdry, consider raking a little volumizing mousse through your roots (Nation loves this one), to make sure you’re getting the fullness you want.

A long, blunt and weighted lob allows for versatility in styling. Read: It looks great with big curla, messy bends, or worn pin straight and glossy.

Soft Curtain Bangs

If your hair is long, a great way to give it extra dimension is to weave in a low-maintenance face-framing bang. Leo Izquierdo, co-founder of IGK tells us the the long fringe is coming back in a big way. “The cut adds a little extra shape to any hair texture, without requiring a ton of bang-specific styling,” Izquierdo explains. “It’s a very French-looking style — simple and sophisticated.”

A shorter, Bardot-esque bang spilling into gradual layers provides a gorgeous, effortless frame around the eyes.

Or you can keep your fringe long — falling down around the chin — for a subtle shape that’s still long enough to be pulled back into a chic ponytail.

If you’re wary of trying something new, just consider a few fringe pieces falling around your cheekbones, which is a good baby step.

The Fringed Bob

The very popular French girl bob — squared off with heavy bangs — is getting a structural refresh in the new year. Arrunategui says everyone will be asking for the angular chop, just with a little more texture. “The perfect Parisian bob falls precisely between the cheekbone and jawline,” he explains. “This variation will look a bit choppier and unpolished, which will give a fresh kind of dimension.”

On curls, this cut will maintain the chin-level length and the blunt bags while some gradual layers thrown in will provide even more fullness.

If your hair is thin, try introducing some edge to the chic style by adding a very thick, eyelash-skimming bang with heavy layering throughout, then just style it with texture spray (Arrunategui likes this one) for even more body.

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