How I Wear My: Gray

Happy November and welcome to the 51st post in the How I Wear My series!

Jill of Everything Just So and I are thrilled to be celebrating the 4th anniversary of How I Wear My!

This style series would never have made it so many years without all the fashionable participants. Bloggers, readers and friends – men and women alike – from all over the world have made How I Wear My last as long as it has. Here’s to many more years of showing off how we all wear today’s biggest trends and classic favorites. Thank you!

It’s a busy but thrilling time of the year, with Halloween over and Thanksgiving on its way, the temperatures dipping into sweater and coat weather, and the realization that 2015 is coming to a close. Already? But can we make time for a little elegance and glamour? Because Jill of Everything Just So and I wanted to highlight one of the most beautiful neutrals around—gray!

Jill of Everything Just So gets us started with her look featuring gray and says, “I am wearing a charcoal gray shawl-collared cardigan from Express with a J. Crew crystal baguette necklace and Tahari patent loafers in Ruby Red. I think gray is such an elegant color any time of the year but especially in the fall!”

HIWM Gray Collage Jill

Tamera of Tamera Beardsley mixes gray with creamy off-white for a stunning fall look. She tells us, “My grey jumpsuit is so easy to style with my closet full of neutrals. I just love how this mid-grey shade plays beautifully with creams and whites! Grey gives my creams and whites a whole new visual depth.”


Malia of Style by Malia looks cozy and stylish in her gray look. She says, “This is my favorite fall sweater. It is eons old but it is the perfect shade of grey and I can’t wait to pull it out every fall. I pair it with so many things but cropped ponte pants and a black turtleneck are a go-to. Plus the beaded and tassel necklace really makes it pop.”


Cynthia of My Rose Colored Shades is the epitome of fall style in her gray cardigan with leopard pumps and flared jeans. She says, “You just can’t go wrong with a cozy chunky heather gray cardigan.”


Imogen of Inside Out Style shows us how she wears her gray in springtime. It’s spring in Australia, after all! She tells us about her fluffy gray cropped sweater look saying, “This is a cheapie from Target (Australia) and cropped styles can make me look chunky, so I make sure I wear a longer top (this one if from Uniqlo) with my Zara jeggings in the same colour so that I’m not highlighting my lack of waist. The leopard print sneakers are also from Target.”

April of Ms B in the Bay Area joins us this month looking chic in gray. She says, “I love wearing gray and this oversized cashmere sweater will look great this winter with skinny blue jeans, black jeans, and white jeans come spring. Such a versatile color and I was so happy when I recently spotted this Joan Vass sweater at Marshall’s for $60…..such a great find!! It looks great with black leggings and camo jeans as well!”


Linda of A Labour of Life keeps warm in the snow wearing gray and says, “This is such a fun outfit for weekend casual – and a snowball fight! I love this grey tweed cardigan and paired it with a pair of grey plaid leggings. It just seemed like a fun outfit to go outside and play in the snow!”



Suzanne of Suzanne Carillo wears feminine floral pants in a few gray shades and a charcoal gray cowl neck sweater. She has this to say about her look: “Grey is a colour I often wear, unlike white or black I find it isn’t too harsh next to my face. The 1970’s burgundy leather jacket was a thrift store find. This hat used to be my father’s hat. I’ve worn it for over 30 years now. It is one of my most loved and most worn hats.”

how to wear grey and burgundy

Elizabeth of Beauty Without Within wears a tailored gray pantsuit and tells us, “Gray is not necessarily one of my best colors; however with accessories and a variety of tops, it works for me. I love the sheen of this gray suit and find it takes me from the symphony to church and other outings requiring a put-together look.”


Nora of Jacket Society wears gray fringe her look, ideal for our mild California autumn and winter seasons. She tells us, “I am wearing our Grey hooded poncho with my H&M cream top and Rag & Bone jeans with one of our chain fringe necklaces. These hooded ponchos come in Merlot and black color as well and they have all been bestsellers. Only a few of each left on our web site.”

Processed with Moldiv

Diane of Pepper Medley wears gray with a splash of hot pink. She says, “When temperatures drop and the leaves turn gold, it’s time for fur and bling in the mountains of southwestern Virginia. Just because the skies are gray certainly doesn’t mean you can’t wear gray with a pop of fun color.”


Ana of Mrs. American Made puts the sunshine in gray with this darling embroidered dress. Ana says, “This was easy because I don’t have too much of this color, just a few pieces. I do own this amazing #madeinUSA Nanette Lepore embroidered dress. I have had it many years now and you can see one way I have worn it – alone as a statement in and of itself. I also wear it with all gray pieces for fall, including tall gray suede boots and a gray cardigan.”


Susan of High Heels in the Wilderness shows us how she wears her gray Vince coat sweater she bought at the Nordstrom Anniversary sale in July. She says “I’m wearing burgundy NYDJ jeans, with a Holt Renfrew brand burgundy and camel scarf and carrying my burgundy Marc Jacobs bag. The coat has become a staple in my fall wardrobe. I can wear it with just about anything…dressed up or down.”


Merci of Chic on Thrift wears a gray dress and matching wide belt and says, “This was a random morning outfit and I like how it looked put together. The scarf on the head made me feel like an Egyptian Princess.”


Trina of Tea Time With Trina mixes cream and camel with her gray and says, “I love this month’s theme, it’s my very favorite color palette. While some women gravitate towards black, some neutrals, others vibrant colors, I find as I shop I always head directly to the shades of grey. They’re just so easy to accessorize with.

This is one way I mix both charcoal and heather greys. Well, actually this ensemble pretty much brings in all shades of grey with just a hint of tan and taupe to carrying it through.”


Beth of Tall Fashion Adventures is ready for fall in Europe and says, “Lately, I’ve been wearing my textured gray sweater with a ‘pop of plaid’ by layering it over a sheer, plaid button-down shirt and completing the outfit with black skinny jeans. Usually I wear flats or booties with this look to give it a preppy vibe. In preparation for a lot of walking around Zurich, Switzerland, I added a little “sporty” to the preppy look by wearing my gray New Balance sneakers.”

Tall Fashion Adventures How I Wear My Gray

My friend, Amy, tells us about her new gray piece and says, “This is my new sweatshirt. Wait no, it’s a blazer! It’s comfy fleece like a sweatshirt but with a little edge and gray and Merlot are the colors of season, right?  The brand is Prana and I got it at REI. I’m actually thinking of switching out the buttons. They are too generic. I’m thinking silver would add just that right amount of pop!”


Alice of Happiness at Mid-Life does a little gray pattern-mixing in her look and says, “I don’t own much gray in my closet. I have this striped top that has light gray stripes and I thought it would go well with the darker grey sweater vest.”


I decided to pull out the poncho again this month. I chose my Cashmere Blend Poncho with cable knit in heather gray from Mason Street Designs and wore it over a light gray tank top.

I wore it with a quilted skirt from Banana Republic (on sale for $37!), DKNY tights, and a black Adora bag. I’m also wearing a birthday present to myself: a pair of suede waterproof booties by Aquatalia.


My Long Crystal Ombre Tassel Necklace in silver and black from Kay and Star ties the look together.


Thank you to all the stylish participants this month. Jill and I love how you all wear gray!

Be sure to visit Jill’s for even more fantastic gray looks!

By time we meet again for the next How I Wear My the holiday season will be in full swing. With so many occasions for dressing up, it would be lovely to break out your best jewelry in honor of the season, and these days we are partial to pins!

How I Wear My Badge

So join us in December for “How I Wear My: Brooch.” Whether it’s an heirloom piece given to you by a family member or some little vintage (or modern) gem you picked up at the thrift shop, we would love to see how you style your brooch! Send photos to us at by December 7, 2015 and be sure to include details!

And don’t forget to register for the Work Your Wardrobe webcast put on by Stella Carakasi on November 12th! Get the details and register here.


Make it a rich day!




  1. Kathy
    November 4, 2015 / 5:56 am

    Everyone looks wonderful, I think gray is a universally flattering color and one of the staples of my wardrobe. Goes with everything. I even have gray flannel slip on sneakers.

    • Adrienne Shubin
      November 4, 2015 / 7:08 am

      Hi Kathy, Gray does go with everything. I can’t think of a color it doesn’t look great with! I wish I had more of it in my closet! I love it best with cognac and off white – like Tamera and Trina’s outfits. xo, A

  2. November 4, 2015 / 6:24 am

    Love all the grey looks. It’s confirmed, I need to add more grey to my closet.


    Hope to see your Thursday for TBT Fashion link up.

    • Adrienne Shubin
      November 4, 2015 / 7:06 am

      Hi Alice, Thanks for joining us this month. I need more gray too. I thought I had a lot of it but it turns out I only have a few gray pieces, some not so cute that I need to donate.
      I will link up with you Thursday!

  3. Jill
    November 4, 2015 / 6:26 am

    Everyone looks so polished and wonderful. I love that shot of Diane in the hot pink and gray, with those gorgeous leaves behind her. What a pretty picture! Cheers to you my dear, thank you for 4 years of stylish good fun! xx

    • Adrienne Shubin
      November 4, 2015 / 7:05 am

      Happy 4th HIWM anniversary, Jill!
      I love Diane’s photo too….those trees against her pink jacket. So vibrant!
      Here’s to many more HIWM years – or at least a couple 😉
      Thanks for all your hard work and commitment over the years. I’m so grateful for our friendship! xo, A

  4. November 4, 2015 / 7:41 am

    Another fabulous roundup my dear! So happy to see you have found the beautiful Kay and Star necklaces! I thought you would really enjoy their line! You model them with savvy style darling!

    Please give gorgeous Torie a big birthday hug from me!


    • Adrienne Shubin
      November 6, 2015 / 8:45 am


      I am in love with your off-white and gray look! It’s so fabulous – California Chic!
      Kay and Star make such cute things at such great prices.Thank you for introducing me to this great shop!
      I will be sure to tell Tori happy birthday…same to Slater!
      xo, A

  5. November 4, 2015 / 9:27 am

    What a wonderful roundup this month. Featuring my favorite color palette, giving me all kinds of styling inspiration. Your outfit, in my opinion, tops them all. You wear the poncho so well and that mini skirt looks like it was made for you. But the way you topped the entire ensemble off with that tassel necklace was splendid. Thank you so much for all the time consuming work you put into this monthly post.

    • Adrienne Shubin
      November 6, 2015 / 8:49 am

      Thank you, Trina, that is so sweet of you to say! Truth be told, I was feeling anything but stylish that day. I need to remember this outfit for when I am just not “feeling” it, you know?
      I love that tassel necklace with the poncho…just finishes it off so well and breaks up the solidness of the poncho.
      I love the way you mixed camel with your gray. That is one of my favorite color combinations – as well as gray with off white like Tamera is showing us.
      Hope to see you for Brooch next month. Thank you for participating!

  6. November 4, 2015 / 9:57 am

    Everyone looks fab in their gray ensembles and I love your necklace Adrienne! Thank you so much for hosting yet another successful HIWM!

    • Adrienne Shubin
      November 6, 2015 / 8:45 am

      Thank you for joining us, Nora!

  7. November 4, 2015 / 10:58 am

    Thanks for including me, I was so worried I had missed it this time. Lovely looks on everyone.

    • Adrienne Shubin
      November 6, 2015 / 8:45 am

      Hi Linda,

      Thank you for joining us! See you next month, I hope, for Brooch!

  8. November 4, 2015 / 12:31 pm

    🙂 Thank you, for putting all this together, dear Adrienne!
    It’s so much fun to look at the ideas all my fellow bloggers had.
    I enjoy this every month again and again and again.
    Greeting from cool Vienna,
    Claudia 🙂

    • Adrienne Shubin
      November 6, 2015 / 8:43 am

      Claudia, Thank you so much for joining us. I love your beautiful scarf look on Jill’s blog. Hope to see you for Brooch next month!

  9. November 5, 2015 / 4:23 pm

    LOVE GRAY! I am so happy it is big this year. I love your cashmere poncho. I have a very similar one that I purchased on sale last year at Nordstroms. I wore it non stop. I love those aquatalia boots and have been pining after them myself! All of the ladies look lovely!

    • Adrienne Shubin
      November 6, 2015 / 8:42 am

      Cindy, I find myself reaching for my light gray poncho all the time! It’s so versatile and an ideal layering piece.
      The Aquatalia booties were a big splurge for us but I knew I would wear them all the time (already wear them almost daily) this fall and winter – waterproof, so comfortable and well made. I will have them for many years to come and they are ideal for travel.

  10. November 5, 2015 / 5:59 pm

    Gray is my favorite neutral and I loved seeing all the looks featuring this cool color. Also, happy happy 4th anniversary to HIWM. I’m sure it’s a lot of work to put together these monthly features, and I appreciate that you and Jill do it because it’s so much fun!

    • Adrienne Shubin
      November 6, 2015 / 8:40 am

      Thank you so much for participating, Beth! I love having a fellow tall woman in the mix.

  11. November 7, 2015 / 12:46 am

    Thank you so much for including me in this post. I was honored to be part of this spectacular group of women.

  12. November 7, 2015 / 3:08 pm

    Adrienne! I love, love, love the poncho look together with the tassel necklace. I must try that with one of my new ponchos (I think you saw the blue-gray one on IG) – I might even be brave enough to try it with a skirt just as you have done here since I like the look so much. Thank you again for hosting these great posts every month. Looking forward to brooches! : ) Ana

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