When it comes to short hair, there are two types of women: the type who feel sure enough to have their hair shorn, and those who feel the need for more length to their hair—their mane becomes a security blanket of sorts. “It’s a confidence thing,” says Brennen Demelo, owner of Brennen Demelo Studio in Toronto. “I encourage every woman to try it, though, you’ll feel liberated and powerful,” he adds. To make it a little easier, transition into a short cut slowly. “Go in stages—take a few cuts to get to a short cut and enjoy the different looks along the way. And once you find the length that works for you, play with texture or different styles and see how your hair moves,” he says.

However, if you decide to go short all at once, make sure it’s not during an emotional time in your life. That is, don’t pull a Felicity Porter. “If you’ve just been through a breakup, are having a midlife crisis or have been let go from a job, don’t cut off your hair in this vulnerable time,” says Demelo. “”If you do it on impulse like this, it could leave a bad taste in your mouth. You need to take the time to figure out what cut will work with your daily regimen.”

If you are ready to take the plunge, here are six
short cuts that never fail. “What works about these looks is that they hold their shape throughout the cut. Since short hair tends to need more attention, these classic styles will hold their shape longer,” says Demelo.

The short cut: The bob.

The bob can be cut anywhere from above the collarbone to the top of the ear. While it works best on a woman with balanced, petite features and a small face, the look can be adapted with slight changes to suit your look (see “The graduated bob). However, if your hair texture is thick, coarse or curly, skip this cut.

The short cut: The graduated bob.

With length on the pieces that follow through to your chin, the graduated bob will work well on you if you want to have the feeling of longer hair, and if you have a broader face (“The angles will help pull out and narrow the appearance of your face shape,” says Demelo).

The short cut: The crop top.

This choppy, short cut (think Michelle Williams) is the shortest of the ones on this short list, with a messy, tousled look and geometric shapes in the cut. “This cut will help you expose great features,” says Demelo.

We’re not done yet … 3 more short hair cuts that always look amazing on the next page …
The short cut: The disconnected cut.

The sides are cut shorter than the top, where you have longer, more floppy pieces of hair, creating a more square, androgynous style. “With this look, you can do variations in styling—flip it back or forth,” he says. “It has an edgier feel.”

The short cut: The short bob with a short fringe.

With the baby fringe, this look opens up the face. “It’s gives a modern edge to a classic cut, and you’ll see a lot of this style this season,” says Demelo. It evokes a 1920s feel but with a modern spin thanks to the round shapes and texture. This style would well for you if, for example, you work in the corporate world and a disconnected cut is too edgy and you need a cut that’s more professional.

The short cut: The layered shag.

“Layering the hair with shorter points on top and long points on the bottom creates a softer feel around the perimeter,” says Demelo. Halle Berry’s hair is one gorgeous example, but the beauty of this cut is that if you want to feel some hair around your neck, you can do a longer version of her shag cut.

Read more:

Our 7 favourite short hair styles

5 short hair cuts to try now

5 healthy hair secrets