5 Essential Questions To Ask Yourself When Choosing a Hairstyle


5 Essential Questions To Ask Yourself When Choosing a Hairstyle

How do I find a hairstyle that suits my face shape?  This is the question that we were asked to discuss and share our thoughts on.

In this video, Jill Chivers of Shop Your Wardrobe and I discuss the 5 essential questions you should answer before you cut your hair or choose a hairstyle!  Face shape is just one element of the equation, discover the other four that are important to consider when discussing your hairstyle options with your hairdresser.

1. How Much Time Are You Prepared to Spend Doing Your Hair Each Day?

There are a few different kind of people in this world regarding spending time on their hair.  Which of the following answers the question about how much time you’re prepared to spend doing your hair each day?

  • Are you wash and wear?
  • Are you prepared to spend 1-5 minutes per day?
  • Are you prepared to spend 5-10 minutes per day?
  • Are you prepared to spend up to 30 minutes or more per day?

Why is this question important?

When talking to your hairdresser this will give your hairdresser an understanding of how complicated your hairstyle can be and how much maintenance you’re prepared to do each day to make the style work and look great.

2. What Will Your Hair Texture Naturally Do?

What kinds of styles work well with your natural texture versus which ones will take more styling and product?

Then relating this back to your lifestyle requirements (the questions above) your hairdresser will get a better idea of the possible cuts that will work for you.

  • Curls versus straight hair
  • Coarse versus fine hair
  • Cowlicks
  • Crowns
  • Direction of hair growth

All these elements will influence the kinds of cuts that work best for the physical elements of your hair.

3. What’s Your Face Shape

Is your face longer or shorter, wider or more narrow, balanced jaw and forehead or unbalanced? Learn more about figuring out your face shape here.

These considerations will influence what flatters your face.

Ideally, you want to think about creating a balanced appearance and hair works just like clothing, using the optical illusion of horizontal to widen (or balance) and vertical lines  to lengthen and elongate.

  • Use hair to shorten a longer face shape (oblong, rectangle, some hearts and diamonds)
  • Use hair to length a shorter face shape (square, round)
  • Use hair to balance a feature (heart, diamond, triangle/teardrop)

How to Figure Out Your Face Shape

4. How Do Facial Features Influence Hair Style?

Facial features, along with face shape also influence the styles that flatter us.

Longer forehead  – do you need a fringe/bangs to shorten this feature down and make it less prominent?

Small or large facial features – Large facial features look best with more voluminous hairstyles (rule of scale)

High or low ear placement – influences how masculine your jaw appears and how long or short hairstyles appear.

Longer jaws tend to look more masculine and so it’s harder to look as feminine (if that’s important to you) with a very short hairstyle that doesn’t include hair around the nape of your neck.

This measurement we discuss is around 5cm  (between the base of ears and bottom of chin) for longer or shorter hairstyles being more flattering.  Check out this post on who suits a pixie hairstyle for more tips.

Where do you want the focus  – think about hair being able to “point” so it’s best to avoid strands of hair that point at a larger nose or a softer jaw, or any feature you’d rather wasn’t the focus of your face.

5. Should You Cut Your Hair Short When You’re Over 40?

Let’s talk about Age…Why is this rule still around?  Why did it exist at all?

Why is this rule still around?  Why did it exist at all?

I believe it developed because hair dyes don’t work as well on grey hair, until more recent hair dye technology has overcome this issue, more women who went grey around the age of 40 had grey hair.  Grey hair can also become more coarse and can look straggly if it’s not thick too and for many, it can remind us of the stereotypical “witch”.  Cutting grey hair shorter into more modern and funky hairstyles means that hair was shorter more frequently over the age of 40 in the past.

Cutting grey hair shorter into more modern and funky hairstyles means that hair was shorter more frequently over the age of 40 in the past.

These days hair products and dyes are much higher in quality and can keep hair looking in great condition for much longer, no need to cut off your hair!

Plus 40 is no longer considered “old” in the way it was 40 years ago when 40 was likely more than halfway through the average lifespan.

Some Other Questions to Ponder

  1. Does this hairstyle suit my personality?
  2. Does this hairstyle reflect who I am and how I want to be perceived?
  3. Does this hairstyle work with my style recipe?

Hairstyle selection, you can see, is so much more than just “face shape” related!

Further Reading on Face Shape and Hairstyles

Importance of Placement of Facial Features For Determining Face Shape

Best Hairstyles for your Face Shape – Round

Best Hairstyles for Your Face Shape – Oval

Best Hairstyles for Your Face Shape – Heart Shape

Best Hairstyles for Your Face Shape – Square

Best Hairstyles for Your Face Shape – Rectangle

Best Hairstyles for Your Face Shape – Diamond

Best Hairstyles for Your Face Shape – Oblong

Best Hairstyles for Your Face Shape – Pear/Triangle/Teardrop

Download free style ebooks and printables


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  • An extremely obnoxious and expensive hairdresser once told me that I ought to be prepared to spend 45 minutes a day on my hair. That was my one and only visit. Not only is that a ridiculous amount of time for anyone to take, at the time, I had a demanding, unpredictable, deadline-driven job. Right, “See you in 45 minutes, I’m doing my hair.”

  • More than 30 years ago, I wanted an asymmetric hair cut, but was not confident enough to ever do it. About three years ago, I finally cast all caution to the wind and did it! What a revelation! Strangers come up to me and remark how much they like my hair cut. My hair is straight, fine and does not want to curl. So, in addition to having the haircut I wanted, I now get compliments and the best part is I have nearly zero upkeep. Wash, comb out, let dry naturally. Bonus…people are looking at my hair, not my thighs! Since I have many asymmetric parts (one eye higher, one hip higher, one breast larger, etc.), I think an asymmetric haircut should have been the natural choice all along. Duh! Why did I wait so long?!

  • Imogen, I am so happy that I found you! After reading your post about the 5-2 diet, I lost 25 pounds! You are SO knowledgable and SO generous in sharing it. My asymmetric haircut is only one of the things I have reconsidered since I started following you. THANK you for all that you do!

  • Hello Imogen,

    I’m a silent reader of your blog. And this one is very informative and worth sharing for. This is a really big help to others who can’t decide or choose the best hairstyle for them. Hope you will continue to writing more kind of this article. Thanks and best luck on your blogging.

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