Should I Cut My Hair Short for the Summer, and Other Exasperating Questions I Ask Myself

No seriously, will short hair suit me? 'Cause just look how cute this haircut is...

If you’ve ever asked yourself, “Should I cut my hair short?” then the quick answer, if we at All Things Hair have been doing our jobs correctly, is a hard yes. There are a slew of options for every face shape and texture that can work for short hair, and the answer, at least from an editorial perspective, is quite obvious.

HOWEVER.

I personally have had a love-hate relationship with bobs over the years, and have also had tons of “should I cut my long hair or not, no but really?” fits that seems to come on season after season (Which are then invariably followed by “but how short should I cut my hair, though?” There’s really no winning this.). In addition, depending on which hairstyles look great on my current #WCW, the answers to these questions change mercurially as well. To quote Alyssa, our Beauty Editor, “If hair grew overnight, I would try out all these looks.” Truer words have never been spoken. And the fact that we’re inundated with all trends, all the time is never good for my hair ADHD.

Alas, hair doesn’t grow overnight (I’ve tried, sorry folks), or even sprout as eagerly as the tulips on a New York City sidewalk in the summer. So to help any and all of you who might be going through a similar crisis, and perhaps to better talk myself through this decision, I put together a quick checklist to make the process a bit less frustrating. Hey, we’re all in this together, right?

should I cut my hair short into a blunt bob?
The haircut of my dreams, if weather/foreheads/jawlines/ weren’t an issue. #sigh #90sgirlforever

1. Face Shape

Like I said, each face shape has a short haircut that flatters it the most. I have a heart-shaped face (that morphs into an inverted triangle come stomach flu season) so I’ve found that blunt bobs suit me best. Would I suit short hair that’s cut in a concave or stacked style? No, as this top-heavy look makes my forehead seem wider than a soccer field. That said, each one of us already has their best canvass; work with it.

Also work with your stylist to figure out the best short cut for your face shape. Take their advice to heart; they are professionals that can steer you in the right direction when the time comes to take the plunge. And be sure to bring in some pictures of those swoon-worthy short haircuts you’ve been Pinteresting away, so you can see eye to eye. Don’t worry about seeming fussy! There’s no room for buyer’s remorse here, at least for the next few months: Remember that hair only grows 6 inches a year, so there’s literally NO HARM in being overprepared for this. I know people who have actually cried in the artist’s chair after a bad haircut.

2. Lifestyle

Another relevant question: Will I suit short hair that takes more than 10 minutes to style each morning, or am I more of a wash-and-go kinda gal? I thought long and hard about this, as it really, truly depends on where my mind is at the moment. I’m a mood dresser, and my hair ~lewk~ for the day usually follows suit, i.e. if I feel bright and chipper, I’m putting in those extra 15 minutes with a curling iron.

Conversely, if I wake up with the Hangover of the Century (or am running late to Pilates), then it’s most definitely a snooze-button-loose-bunnin’ sort of day. But these options don’t usually come with having shorter hair, as there’s oftentimes no escaping your fate after you shower. Pick a style that you’re happy to play with every day, whether it’s blowing it out, going the full nine yards or letting it air-dry into whatever shape it pleases. Too harsh a reality? Then don’t cut it.

Another thing to consider is whether you or not you’re up for the maintenance. Unless you’re willing to commit to regular trims, learn a proper salon-worthy blowout for big-ticket nights or are into playing up your texture in different ways, then stick to a hair length you can get—and then subsequently forget about—during those times when you just can’t even.

should i cut my hair short into a soft bob
Soft, blunt bobs make me happy. Photo credit: indigitalimages.com

3. Current Fashion

Next thing I considered: Should I cut my long hair into a shorter look if most of my clothes are more on the romantic, feminine, traditionally girly-girl side? A lot of people don’t consider their clothes and manner of dressing when it comes to picking a hairstyle, which I personally feel is a misstep. Your hair is an extension of your personality, just as your fashion taste is—which means, it only makes sense they coexist in peace and elevate the other, like marshmallows in hot chocolate (Ed’s note: If you disagree with marshmallows, we can’t be friends).

Not to say that one should dictate the other, but if a pixie or a bob looks completely jarring to you when paired with your frilly outfits, or if you can’t imagine how to even begin to style your hair during formal events/for your evening outfits, then maybe reconsider (Also, we might not be doing our jobs well, because that shouldn’t be an issue). Understand: You wear your hair every day, so choose a look that’s forgiving on both your features and your fashion choices.

Nota bene: After much deliberation, I realized that I wanted to try out far too many hairstyles than a bob would allow. Not to say I won’t be doing anything to my super-basic, straight hair for the upcoming season—so, hmm, maybe a chunky lob? OMG, that’s another story altogether.