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How to Wear Gray Jeans

How to Wear Gray Jeans - The Well Dressed Life

In our most recent Sunday Sales post I highlighted these gray jeans from Wit & Wisdom, on sale at Nordstrom for only $46. Sizes are still available from 00 – 16. I find they run true to size. 

Our readers LOVE Wit & Wisdom, they are a top selling brand. 

So today, I’m showing you how to wear gray jeans this season, and using them as our key piece. 

How to Wear Gray Jeans

Gray Skinny Jeans


Gray Jeans, $47 

Wit & Wisdom makes a solid jean at a nice price point even at full price, which is always under $100. They have great stretch, wash well, and hold their shape. 

So if you are looking for any kind of jean, put them, as a brand, on your list to consider. 

Talking specifically about these gray jeans, a few things to call out. First, the fray hem is a cute detail that keeps the piece casual. 

You want these to hit you at our around your ankle, similar to how they look on the model. Any shorter and you’ll start to look like you’re wearing floods. 

I created two different looks with these, but want to note before we break down outfits that these also a great option if you want throw on a sweatshirt and sneakers.

You could also wear your striped Breton with casual loafers. 

You have lots of options. 

How to Wear Gray Jeans this Spring 

two outfits featuring gray jeans

Today, I wanted to talk specifically about prints in the first look and the body suit in the second. 

I know, I know, a bodysuit? Stay with me. 

Casual Feminine 

Gray jeans, pink blouse, white foldover clutch, white woven sandals, pearl stud earrings

Floral Smocked Shirt, $79 | Woven Strap Sandal, $99 | Foldover Clutch, $25 | Pearl Stud Earrings, $50

There is a reason why I don’t feature many prints and patterns here that warrants a bit of a conversation.

Why I don’t feature many prints and patterns.

First, I find the majority of prints in women’s retail either juvenile or lacking sophistication. 

You don’t want the print you are wearing to be the first and only thing you see in your outfit. If you do, that’s cool, but that style doesn’t fall into the classic, timeless and modern category we cover. 

Often, when I do find a print I like, nine times out of ten, I hate the style of the blouse.

Sometimes I find a flattering print and style, get excited for a minute, and realize it’s $500.

And no one would be happy with me if I featured a $500 blouse.

So to find a blouse with a pretty print, flattering shape, and is under $100 – that’s a unicorn. 

This pink floral blouse from Vince Camuto works so well here. There are tiny flecks of gray in the pattern that go beautifully with the jeans.

And the style is feminine and romantic without being over the top.

I appreciate that they kept the neckline clean and in a v-neck and put the details on the sleeve. It’s a much more flattering cut that all body types can wear.

So, of course, I love this blouse, and it was in stock yesterday at Nordstorm and sold out overnight.

But I found sizes here at Dillard’s online. And, please don’t send me mean emails about lack of sizing, I have no control over it, and I’m as frustrated as you are

The blouse is also available in blue and would look great with any blue denim or white bottom you have. 

I’m using these popular woven sandals for shoes in color “new cream” also from Vince Camuto. I have these in the Dulce color, and they run true to size. I also have a wider foot, and they are very comfortable. 

Then, two details I don’t want you to miss. 

First, this ivory fold-over clutch is only $25 on Amazon, and it’s fantastic for spring. You’ll carry it all the time if you like clutches. 

Second, these $50 floral pearl earrings are gorgeous; I picked them because they mimic the floral pattern of the blouse. And I used the silver tone to work back to the gray and complement the silver-tone zipper on the clutch. 

This little detail creates a soft and composed look. 

Polished Casual


Gray Jeans, white bodysuit, black linen blazer, black flats, black leather tote, and gold hoop earrings

Stretch Linen Blazer, $188  | Scoop Tee, $17 | Flats, $145 | Leather Tote, $450 | Hoops, $14

Next is a more structured outfit that you can take to brunch or the office, depending on your industry.

I’m using the Stretch Linen Blazer from J.Crew. It’s a simple, classic cut, lightweight blazer in regular, petite, and tall from a 00 – 24. 

If you have the Madewell Boyfriend Blazer, that will work here, too – note that the J.Crew option is more fitted and the Madewell blazer is boxier. 

Ok, now for the under piece. You can wear anything you want: a white tee, the Nic + Zoe Perfect Tank, but I tried this bodysuit and was pleasantly surprised. 

For the record, I will never wear it without a blazer or sweater on top, but I love how smooth it fits and finishes the outfit so nicely. Size up if you order. 

Here’s a fun tip I learned, you don’t have to snap the bottom to get the smoothing effect. Instead, you can just put it on and tuck the bottom under, as if you were going to snap it; this will give you a little more room if you have a long torso. 

For shoes, I went with the Rothy pointed flats for shoes. You can wear any black shoes, from a pump to block heel sandals. 

Then, this STUNNING and expensive bag from Marc Jacobs – remember, my job is to give you options, there are lower priced alternatives throughout the site. 

And, finally, my favorite gold hoops from Amazon because the hardware on the tote is also gold tone. 


How to Wear Gray Jeans

Related Posts

 Join Megan Kristel for a comprehensive, 3 hour long, LIVE Virtual Workshop sharing personal style and shopping tips for women over 40 on March 31, 2023.


Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.

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Wednesday 30th of March 2022

I like gray jeans but haven't been able to find any in curvy. Would it be possible to occasionally include curvy options? I'm a small size but find that curvy jeans fit better than regular jeans. I like the curvy jeans at AT, Loft and WHBM but none of those companies have gray jeans now.


Monday 24th of October 2022

@Dee, Try Express, they have Flex fit which is a great curvy option.


Sunday 3rd of April 2022

@Dee, I am curvy and was pleasantly surprised that these Wit and Wisdom jeans fit me well! Give them a try. Megan, I ordered both the bodysuit and the jeans, and I’d have to say that prior to this post, I would never even think of buying either a bodysuit or gray jeans, but both fit me well and I really like them! Thank you! 😊


Wednesday 30th of March 2022

Thanks so much for this thoughtful and informative post. I ordered the grey jeans on Sunday and am waiting for their arrival. In the meantime, I am wondering if a navy blazer would be a possibility to pair with the grey jeans?


Wednesday 30th of March 2022

I agree about prints being unsatisfactory in womenswear. I feel like we wear “ menswear “ styles a lot, in most clothes lately, so stripes are used more often. I wonder if it’s easier to produce menswear styles, then the sewing is generic, and maybe faster? Interesting to ponder…

Jude A

Wednesday 30th of March 2022

This was a great post! I love how you put in lots of options and also the tip about the bodysuit (not having to snap it up.) I have a couple of bodysuits and don't wear too often because snapping them up is a real pain (and yes I have a long torso.)

Also - I hope you don't get many "mean" comments. I think the whole idea is to see what you have chosen and find something similar that would work. You do great work here and I really appreciate you!


Friday 2nd of March 2018

Amazing post! This may be my grey jeans tipping point!

Megan Kristel

Friday 2nd of March 2018

You would get so much wear out of them! xx