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Going short: Short hair whisperer Greg Gilmore dishes on everything you need to know before and after your big chop

Posted on December 10 2015

Hair Guru - Greg Gilmore

Hair Guru – Greg Gilmore

“A woman who cuts her hair is about to change her life.” Coco Chanel

I’ve always been of the thought that I am not my hair. I’ve never felt moved to engage in the “naturalista” movement nor have I ever felt the need to defend my use of a hair relaxer or as some of us affectionately call it, “the creamy crack”. I’ve worn braids, extensions and even bangs. I’ve had good hair days and bad hair days. Through my teenage years and early adulthood, I went through many hair phases and stages and although my hair styles were an extension of my self expression, they never defined me. But, a funny thing happened to me two years ago. I cut my hair and magically, I came into my own.

Wemi Pixie Cut | Cut by Greg Gilmore

Wemi ‘s Current Pixie Cut | Cut by Greg Gilmore

On a beautiful L.A. Sunday afternoon, I sat down with Hair Stylist extraordinaire, Greg Gilmore to discuss all things short hair. In a city where everyone you meet is an expert at something and a guru to many, it’s hard to take things at face value or even word of mouth. Gilmore’s work speaks for itself; I get asked about who cuts my hair at least 3 to 4 times a week.

I’ve dubbed him the “short hair whisperer” not only because I think he’s actually subconsciously whispering to my hair as his scissors weave through my strands but because I’ve never seen a more talented pair of hands move so easily and seamlessly through a head of hair –as if they were born to do just that.

When I decided to cut my hair, it was because of a nagging feeling that I was carrying around dead weight (both emotionally and in an uninspired daily ponytail). Something needed to change and the hair was the lowest hanging fruit. I came into Gilmore’s salon with several references. Michelle Williams (à la her ads for Vuitton), Ginnifer Goodwin (pre-Once Upon A Time), Angela Bassett (post- setting her husband’s car on fire in Waiting To Exhale) and Nia Long (everyday in the 90s).

Michelle Williams's choppy bob was a starting point on my hair vision board. Gilmore explained that my infatuation was actually with the messy way the hair was styled rather than the bob itself.

Michelle Williams’s choppy bob was a starting point on my hair vision board. Gilmore explained that my infatuation was actually with the messy way the hair was styled rather than the bob itself.

The actress's Mia Farrow inspired pixie also caught my eye.

The actress’s Mia Farrow inspired pixie also caught my eye.

So did Ginnifer Goodwin's dark brown and slightly messy pixie.

So did Ginnifer Goodwin’s dark brown and slightly messy pixie.

As did Rihanna's chic pixie.

As well as Rihanna’s chic pixie.

I’m well aware that none of these cuts actually have much in common except being short but in spite of my all-over-the-place hair vision board, Gilmore and I found some common ground. We started with a deconstructed asymmetrical bob which months later got cut into an edgy pompadour and eventually went shorter and settled into my beloved pixie. Below, Gilmore and I discuss everything from the everyday woman’s trepidation to go short to tips on maintaining your cut once you finally take the plunge.

Halle Berry's famous pixie. The actress has often spoken about how going short kicked her acting career into high gear.

Halle Berry’s famous tousled short cut is a cut Gilmore says a lot of his clients still request. The actress has often spoken about how going short kicked her acting career into high gear.

Another star whose career skyrocketed after going short was Rihanna.

Another star whose career skyrocketed after going short was Rihanna.

W: I love hearing about your foray into cutting hair. Your first cut was kind of an accidental bowl cut that turned out to be pretty stylish, right?

GG: Well, I always liked and admired short hair. There was just something very bold about it. I was also very scared to cut people’s hair because if you make a mistake, you’re not only destroying that person’s hair but their confidence as well. Anyway, this lady walked into a salon where I was working at the time and she was very insistent on cutting her hair off. I had only been doing hair for about 2 years at this time and I’d never done a big chop before. No one else was available to take her and one of the other stylists encouraged me to give it a shot. Of course I didn’t tell her that it was my first cut but I gave her a pep talk and told her it would look great.

I started cutting and remembered a few tips from other stylists like cutting the hair all the way around and making sure everything was all lined up. When I finished the cut, it came out really well and I was so excited –more for me than her because it could have gone really wrong. I told her at the end that it was my first cut and she replied with “Oh”. She never came back but I had my confidence to keep cutting.

W: That is hilarious. A sign is a sign. That client was very adamant about cutting her hair off but it’s not always the case with all women. Why do you think women are so nervous about going short?

GG: I think going short is a scary thing for most women. Women are automatically associated with having long hair. Being beautiful is also associated with having long, luscious hair. I think you have to be very confident in other attributes that you have besides your hair.

W: I remember a friend saying to me post-cut ” I like your short hair but I was really nervous for you because guys don’t like short hair.” My response was of course, “Excuse me, says who?”

GG: Men have been the leading energy in the world for a long time and a lot of women still give them that power when it comes to deciding how they should and shouldn’t look even when it comes to their hair.

W: What advice would you give to someone ready to take that plunge?

GG: Consider your lifestyle and how much maintenance you want to put into your hair. That will help determine how short you want to go. Do your research and see what styles you’re drawn to. Research what is required to maintain the cut you want as well.

W: Speaking of maintenance, how often do you recommend getting cut / trimmed?

GG: Because women tend to have a lengthier cut than men, they come in for maintenance less often. Every two weeks is ideal for a pixie. If you have a lengthier cut like a bob, you can go a little bit longer. A lot of cuts grow out nicely so you can probably manage once a month.

W: How do you know which cuts will grow out nicely?

GG: As a stylist, the longer you’ve been doing this, the more intuitive you become with how different cuts will turn out. I know for example that an A-line bob will grow nicely into a slightly longer A-line bob. I also know that if you have more tapering in the back or a more disconnected cut, it will not grow out nicely and will require a lot of maintenance.

W: Whether you have long or short hair, the goal is to achieve a beautiful, shining head of hair. How do you achieve that with short hair post-salon visit?

GG: That depends on the texture of your hair. If your hair grows naturally straight and you use a great shampoo and conditioner, you can let your hair air dry and it’ll still look fabulous.

W: Do you have a favorite or go-to shampoo / conditioner combo?

GG: I like Paul Mitchell. Design Essentials is great for textured hair and so is Mizani.

W: Let’s talk color. You’ve done some great color work. In the summer, we saw a lot of purples, pinks and blues. What’s trending this season?

GG: Some colors like red never go out of style. This season, I’m seeing less cool and more warm shades of the pastel summer colors that were so popular. Instead of pink for example, I think you can expect deeper and warmer shades of red even going as dark as plum.

W: That’s interesting because Marsala was the Pantone color pick for 2015 so that shift makes sense. How do you maintain a cropped, colored do?

GG: Moisture, moisture, moisture. You have to keep the hair moisturized. You may also want to consider shampooing a little less. Too much shampooing can sometimes dry out the hair. Condition and moisturize.

W: Which celebrity cut are you loving right now?

GG: Halle Berry’s cut is always a classic.

W: She’s grown it out recently but I’ve always loved her slightly messy pixie.

GG: The softly tousled look on top is beautiful. I still get so many requests for that cut. I also liked Jennifer Lawrence’s cut before she started growing it out. Keke Palmer’s short hair is really cute and my favorite is Jennifer Hudson. She wears the short hair so well.

W: Which celebrity head of hair would you like to get your scissors in?

GG: Nia Long

W: Great answer! She’s so beautiful and I’ve always loved her in short hair. She just seems to have the perfect head for short hair. Do you think there’s an ideal head shape for really short hair?

GG: Yes, a small, really cute peanut sized head (laughing). Amber Rose actually has a great head shape for a really low cut.

W: Not everyone can go bald and blonde, that’s for sure.

GG: I’d like to add one more thing, short hair looks best on a confident woman. If you’re going to cut your hair, be confident in your decision. You can have a great cut but without the confidence it takes to wear it, the cut won’t shine and neither will you.

W: Truer words have never been spoken by the hair whisperer himself.

Greg Gilmore’s salon is based in the heart of  West Hollywood in Los Angeles. Connect with him at to book an appointment.

Follow him on Instagram:  @espressso_







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