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How to Wear a Simple Grey Dress Two Chic Ways

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We talk a lot about creating a chic and classic style affordably. No matter how large or small your budget, you need to know where to splurge, spend, and save.

The best tip I can give you is to be selective about every item you bring into your wardrobe, especially those pieces considered a bargain.

Inexpensive, sale-priced, clearance items tend to be where we let down our guard. It’s too easy to throw a $20 top or dress in our carts. But what happens when we do that repeatedly is we end up with a closet that doesn’t make any sense.

You’ve been there, I’ve been there, we’ve all been there.

That’s why it’s essential to know the style you are trying to achieve before you shop and then hold even the most affordable item to that standard.

Today’s dress, this simple Ponte shift from Old Navy, is on sale for under $30. It is the perfect example of what to look for in a “save” piece that adds tons of value to your wardrobe. 

How to Wear a Simple Grey Dress

How to wear a Gray Dress


Dress, $28 (Missy, Tall and Petite, up to XXL)

Ponte knit is ideal for this time of year. It’s stretchy, soft, and fits well. You can dress it up or down. It pairs with everything from tall boots (below) to sneakers and a denim jacket.

This dress works well because of its timeless cut and heather grey color. It’s also not too short, so you can take it to work, dinner, or to run errands. 

Today, I’m showing you two sophisticated looks with this inexpensive piece at the center.

How to Wear a Simple Grey Dress Two Chic Ways

How to Wear a Simple Grey Dress

Layer with Neutrals

Gray Dress with camel coat, ivory scarf, tan knee high boots, and gold hoops

Boots, $268 |  Coat, on sale $99 |  Scarf, $39 |  Earrings, $90 

To say I love this look is an understatement. My favorite way to dress is in layered neutrals. It creates such a gorgeous richness that works for any occasion. 

Here, I paired the dress with these stunning cognac boots from Banana Republic.

Then, a classic camel coat. I picked up a similar jacket last year and have got so much wear out of it. I like this one from Express; it has a flattering tie waist without looking like a bathrobe.

Finally, add an ivory scarf (under $40 at Nordstrom) and pretty pearl and gold statement hoops.

Simple, classic, timeless.

Pair with Basic Black

Gray Dress with black tights, black booties, black and gold belt, and gold earrings.

Booties, $105 |  Tights, $15 | Belt, $45 (on sale $15)|  Earrings, $7.50 

When you focus on wardrobe building, you’ll eventually get the point that you already have everything else you need to create a fresh look when you bring in one piece.

This look is an example of that. You likely already have a pair of black ankle boots. If not, these booties by Vince Camuto are on sale at DSW. Their block heel makes them incredibly comfortable. Pair them with opaque tights to give your leg a long line.

Then, I added this gorgeous belt from LOFT. Right now, it’s on sale for only $15. It’s subtle but has a designer look and feel. Wrap it around your waist to bring in some visual interest.

Finally, small door-knocker earrings mimic the belt buckle’s style, creating a cohesive, thoughtful outfit.


Our Style Content is Inspired by Our Readers

Our readership inspires all of our posts and is not sponsored or paid for by brands or retailers. 

Recommendations are based on my experience as a personal stylist and wardrobe consultant for over a decade. I worked with busy, down-to-earth women who wanted to look chic and feel confident but were often confused by so much of retail. 

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How to Wear a Simple Grey Dress Two Chic Ways

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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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Leslie Fu

Monday 15th of February 2021

For me, grey is the most favourite colour of all time. Many people choose black to be their main or favourite colour, but grey is my best colour and makes me more comfortable than any other colour. Thank you for sharing this information with us and letting us know about it. Keep sharing more such articles like this with us in the future also.


Thursday 4th of February 2021

I bought the similar ponte dress last year in red and black--I can use these styling tips for both! Thank you. Question about the belt--while it looks great in a photo or when one is standing up/just put it on. . .my belts always ride up and move around to unflattering spots as I stand/sit and move throughout the day. In fact, they are always askew and it drives me crazy when the seam from the waist of the dress is above/below/all around the belt. Am I crazy to worry about that and/or is there a fix for this situation? My current fix is. . .don't wear the belt. Help?


Thursday 19th of November 2020

Is this the same dress Okd Navy has last year? I bought it in’s great!

Megan Kristel

Thursday 19th of November 2020

Very similar, the sleeves on this one are slightly shorter, but you can wear them the same way!