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This is Absolutely the Easiest Way to Look and Feel Stylish with Gray Hair

One of the most challenging aspects of going gray is figuring out which clothes in your closet will still look good on you now that your hair is an entirely different color.

Some women – the lucky ones – don’t need to make any changes. The clothing colors they wore before still suit them after they’ve gone gray.

But other women find their favorite clothes no longer look good on them.  

Picking out new clothes might sound fun for a lot of you, but for many of us – myself included – clothes shopping can be a bit confusing and frustrating.

Please note that this article may contain affiliate links.  You can read my full disclosure at the bottom of the page.

What to Wear with Gray Hair: Tips from a Personal Stylist

So that’s why I decided to bring in an expert to help us out – personal stylist Elysha Lenkin!

image of woman with brunette bob and yellow sweater and white pants sitting on steps

Elysha has over 25 years of experience working in the fashion industry, and she offers lively workshops and private client sessions that empower midlife women to make confident fashion choices.

In other words, she sounds just like what the doctor ordered!

Make sure to check out Elysha’s tips below (paraphrased from my YouTube interview with Elysha).


Find Your Complementary Colors

Q: Elysha, how do you recommend women figure out which colors will look great with their gray hair and skin tone?

I use a two-pronged approach to figure out which colors will look best:

  1. We have the physical component, which relates to colors that complement your skin, hair, and eyes.
  2. And then we have the energetic component. Because the bottom line is that there are just some colors that energize us. And when we feel energized in our colors, we show up full of life – feeling energized!

Regarding the physical component, I have a great trick that can help you figure out what colors complement your hair, skin, and eyes:

Look very closely at your eye color (using a magnifying mirror). See all the different colors in your eyes? Those are your core colors…your best colors are already in your eyes!

Regarding the energetic component:

Most midlife women have an idea about what their best colors are and what colors suit them best. They have colors that they love wearing and that energize them.

But when your hair completely changes color, it can throw you off, right?

So my advice for you is: go back to the colors in your eyes, start there, and then start to experiment and figure out which colors you love wearing. Which colors give you energy?

Also, what are other people telling you?

For example, when you show up somewhere and are wearing a cobalt blue blazer, sweater, or blouse, and everybody says, “oh my God, you look amazing today!” – That is a really good clue that this is one of your colors.

So as you’re searching for colors, consider this two-pronged approach. Think about what colors harmonize best with your skin, hair & eyes and also which colors energize you the most.

Elysha Lenkin

Keep experimenting and understand that this is a dynamic process. Be patient, kind, and compassionate to yourself as you’re going through this process because it can be a very vulnerable time.

After all, you’re trying something new, your hair is different, and you’re really stepping into a new look – this is your reinvention era!


Create a Color Shield

Q: Sometimes there’s a color that looked good on me when I had warm brunette dyed hair, but now that I have cool-toned gray hair, that color no longer looks good next to my face. In my case, that’s beige. BUT – nothing’s stopping me from wearing beige pants, beige skirts, etc. It’s really the color next to your face that matters the most, right?

Yeah. So that’s a great example because (for example) I really love this dusty rose color. It’s a very pale pink, and it looks horrible on me. It just washes me out. It drains all my color.

image of petite woman with brown bobbed hair wearing a beige jacket and gold jewelry sitting on a stoop

I look very sick when I wear this color, even though when I see that color on the rack, it’s a beautiful color and I’m very drawn to it, but it is definitely NOT one of my colors.

So if I was going to wear that color, I could wear it on my bottom half or I could use it in my accessories.

Or, I could wear a scarf (in my complementary colors – beige, brown, green) along with a dusty rose top. The scarf would be next to my face, so it would act as a color shield from the dusty rose..

And the other thing I would do is I’d wear gold jewelry because that’s really complementary for me.


I love the idea of a color shield! That’s fascinating. Color theory and how colors work together is so interesting.

Yes – and I think it’s so much fun. One of the things I do with my styling clients is I get them out of black. So many women are wearing so much black.

Or (especially if you’re a professional woman), you end up in navy. The navy blazer, the navy suit, or the black suit.

Once you start to find your way through color and find colors that energize you and harmonize with your features, it can be very invigorating and a very bold choice.

People stand out with color, they get noticed more. So it can be a lot of fun, and it’s just one of my favorite ways to help my clients express themselves!


Shop Your Closet

Q: So, after you’ve found the right colors to complement your skin, hair, and eyes -then what? Where do you begin when you are ready to start shopping?

When you are looking to upgrade your wardrobe, the first place you need to begin is in your own closet. The reason is because you want to understand what you already have, and what you can continue wearing.

And I don’t mean just the things that you’ve been wearing. I’m talking about getting into the trenches with your wardrobe, digging into the back, pulling it all out, and really starting to look at it all and deciding, “is this something that I want to bring forward? Does this work with my new look?”

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Go through your closet and find the pieces that are in your complementary colors and then start building outfits with what you already have. This is also going to help you a lot because then you’re going to get crystal clear about what’s missing.

For example: Try on that blouse that you used to love 5 years ago (but forgot about) with some of your other pants & skirts, and if you find that you don’t have anything that pairs well with it, add that to your shopping list.

I believe that when you have fewer clothes but you have the right clothes, then you will have way more outfit options.

Elysha Lenkin

By shopping your closet, you’re going to be able to create a very specific list so that when it is time to buy new pieces, and when I say new pieces, yes, that can mean new pieces from the stores or maybe you like to shop secondhand.

Shopping vintage is one of my favorite things to do for a couple of reasons. Number one, because it’s just better for the environment and everything about it reduces waste.

But also when you shop secondhand, you’re going to get a more original look, right? It’s easier to find more one of a kind pieces.

Having that desire to bring in newness and shop and get new pieces, that is not the problem. The problem is when you’re buying the wrong things…you’re bringing the wrong things into your closet. They don’t work with your style, they don’t work with your look, you don’t wear them. That’s the problem.

But wanting something new is really just a sign that you’re in your reinvention era, and it is really an exciting time. So you just want to be really deliberate about what you bring in, what newness you bring in.

Elysha Lenkin

Clean Out Your Closet

Q: Now, back to the closet, what is the best way to clean out your closet? What is the best way to decide what to give to charity and what to keep?

Well, it’s really important to get clear about where you’re going in this reinvention era and get really clear about what doesn’t need to come with you.

Your hair changed, your look is different, and you can’t bring everything with you. Everything is not going to work.

My favorite way to clean the closet is to combine it with shopping your closet.

image of petite woman with brown bobbed hair and red jacket and beige pants in NYC street

So, as you’re going back into your closet to rediscover what you have, use this as an opportunity for a closet cleanout.

So the way that it works is that when you find that old blouse from five years ago and you decide that, yeah, you do kind of like this…but then you realize that you don’t have the right pants, and you don’t really have anything to wear with it.

And as you think more and more you realize that maybe it’s not meant to move forward with you.

So what you do is you make a decision. Either you’re going to clear it or you’re going to wear it.

And when you decide you’re going to wear it, you’re going to wear it that week. That’s the way that I do it with my clients: it’s either clear or wear, it’s very straightforward.

Make the decision and take action immediately. So that blouse, maybe you don’t think you have any pants to go with it, so now you need to dig a little harder. Do you have a skirt? Do you have something else that you could wear with it? Maybe a pair of shorts if it’s moving into warmer weather, and then wear it right away.

And then when you wear it, you have to decide, do I like how I feel in this? Is this the vibe I want to give off? Is this the impression I want to make right with this blouse?

You can do this with a few pieces each day and then just make that very simple decision. Am I going to clear it or am I going to wear it? And then take action.

And then if you decide to clear it, it’s really important to get that item out of the closet.

Once you’ve got a big enough bag or however much you’re going to donate, then you can take it to the place where you’re going to donate it.

Donate What No Longer Suits You

Q: Where is a good place to donate? I often give to Goodwill because it’s easy, but I know there are better places, such as a women’s shelter. Do you have any suggestions?

Well, there’s the Dress for Success organization, which is an amazing organization that accepts donations of women’s professional clothes.

Another option is fabric upcycling. We have a bin in my building, it’s in the basement, and you can drop off your old clothes to recycle.

And yes to women’s shelters; you always have to call before you donate because you need to be clear about what they’re taking.

If you go to a vintage store, ask them if they take donations because you never know. Maybe they will.

Another idea is to get together with friends and everybody bring a few pieces that they’re no longer wearing, and then you turn it into a little festive little gathering where everyone shops each other’s stuff. That’s really fun too!

I did that once. We went to a party and then we had to have a fashion show. So if two women wanted the same piece, they each had to try it on, and the other women had to vote on who wore it best. And luckily there were no hard feelings. It was just fun.

Yeah, that’s so fun!

Find Your Unique Style

Q: Now, I wanted to ask you this: Let’s say we’ve got our colors down, and we’ve cleaned out our closet, but we still don’t feel like we know our style. You have a style quiz. I took it myself yesterday and it was pretty spot on. I was amazed. Can you tell us a little bit about that?

Yeah, the quiz is really fun and people are always kind of amazed when they get the results. They’re like, how’d you do that? Were you reading my mind?

It’s a quiz called Find Your IT Factor, Tap Into Your Signature, and Discover Your On-Camera Style!

The quiz is about really showing up in your authentic presentation. And it’s really about locking into what is your signature, what are your unique traits, and it has to do with your visual representation. Alright, your style.

So it’s very quick, it’s free, and it’s fun. You’re deciding what you like and getting a lot of insight into what your preferences are.

And then at the end, I give you a result that can get you started on finding your style.

This quiz is just a beautiful place to get started and to give you some insights into what you love, how you want to express yourself, and how you want to show up.

And then I follow up with some emails that give you some ideas about the way you can put this into action.

If you do take the quiz, then please message me on Instagram or on YouTube. I’d love to hear what your results are!

VIDEO: My Interview with Elysha Lenkin

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