Skip to Content

StarFREE! Wardrobe Checklist Download + Weekly Newsletter DOWNLOAD

How to Wear Old Navy’s Black Herringbone Blazer

I’m not ready for summer to be over, but these outfits are getting me excited for fall style. 

This oversized blazer in black plaid was a reader favorite from Monday’s What to Buy at Old Navy Post. 
It’s selling out quickly, but is still available in XS – XXL. 

As you’ll see below it’s a fabulous transition pieces that will take you through September, Fall and even early Spring, depending on where you live. 

How to Wear the Old Navy Oversized Brush Blazer Three Ways

To be clear, while they are calling this “oversized” it’s not really. It’s just not super form fitting, but it doesn’t look like you are wearing a mens jacket two sizes too big either. 

If you are between sizes go down one. 

Currently the blazer retails for $80 but is 30% off, making it $56. 

With White Jeans

Plaid Blazer, $56 | Tank, $6 | High-Rise Vintage “Perfect” Jeans, $128 | Pointed Toe Mule, $89.95 | Shoulder Bag, $395 | Hoops, $15

Yes, you can wear white jeans all year long.

To help make them seasonless, use a warm white instead of a cool or ultra-bright white.

Here, we’re keeping to the classic combination of black and white.

Featured above are the Madewell High-Rise Vintage “Perfect” Jeans . I wear these so much I should have bought two pairs. They are a true warm white.

We’re pairing them with the $6 Old Navy First Layer Tank.

I’m frequently asked how to pair whites together, and the simple answer is that you have seen the items together in person. You can’t tell online.

Then you can see if the undertones match.

I have both of these pieces and they make a lovely white matching column.

To ground the look we’re using classic, polished pieces. 

The black mules with a gold chain detail, and this updated Coach shoulder bag work so well together. The gold-tone accents on both the shoe and bag work as an accessory. 

And add your go-to daily jewelry and a classic gold hoop. 

With Light Jeans

Rib Knit Tank, $20 | Mid Rise Jeans, $138 | Sneakers, $140 | Crossbody, $395 | Hoops, $15

Next, let’s do a chic, casual outfit. 

We’re using another pair of Madewell Jeans, this one in a mid-rise with the slightest hint of distressing.

This ribbed tank from Amazon’s The Drop is fabulous for an under layer. I bought one on Prime Day, turned around, and ordered two more in black and three in white. 

Available in XXS – 5X.

It fits so well it’s crazy, and for under $20, it’s a total steal. Also, it says it’s a razorback, but I can easily wear a regular bra with it.

Then, I love the contrast between a super polished bag and sneakers. It looks so effortless. 

Here, I’m using an elegant crossbody by the brand DEMELLIER. And while $400 is a considered purchase, it reminds me of a better, modern version of the popular Chloe Marcie bag that retails for about $1500. 

And for the sneakers, one of your favorites,  the Veja Esplar Leather Low-Top Sneakers. This look needs a low-top sneaker because you want that slim profile to balance the jeans’ length and the handbag’s clean lines. 

Don’t forget the famous Amazon $15 hoops because I love them.

With Coated Jeans

Coated Jeans, $65 | Rib Knit Tank, $20 | Pumps, $140 | Bag, $100 | Ring, $170

How fun is it to take a relatively inexpensive blazer and make it something special? 

We’re doing that with these black coated jeans from KUT, also pretty fabulously priced. They are a top seller for the month of July after featuring them in the Nordstrom Sale and in our Fall Trend round ups

I ordered the black and brown, because the price and fit is awesome. 

The texture in the blazer paired with the leather-like coating on the jean is perfection. Add the Amazon Rib Knit tank for the under piece

Everything else is simple, you probably already have a pair of suede pumps, like these by Sam Edleman, and a fun cocktail ring for something different. 

Finally, this envelope clutch with a shoulder chain by Rebecca Minkoff finishes the look and is on sale at Zappos for $100. 

52 Outfits in 2022!

Follow Us on Instagram!

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. 

Some links are affiliate links, which means if you purchase via our site, we receive a small commission.

If you enjoy our content and would like to help us grow, please  follow on Instagram and join our Private Facebook Group to access more advice and exclusive in-depth conversations with other like-minded women.

Learn about our mission to help women look and feel their very best, every day, here

Sign Up for Daily Content and Receive Our Free Classic Wardrobe Checklist


How to Wear Old Navy\'s Black Herringbone Blazer

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.

Never Miss a Post

Enter your email address below to sign up for our newsletter and get your free copy of our Wardrobe Essentials Checklist sent to your inbox.

Leave a Comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.


Tuesday 17th of January 2023

Hi Megan! I love your posts! I have a question I’ve been meaning to ask for awhile. How can I confidently wear high heels? I am also 5’10” tall and avoid wearing any heels that are over 1 1/2” tall. Mainly it’s because I feel uncomfortable towering over everyone and especially hate the comments from people about my height (so rude, right?!). Flats and low heels are so limiting and I’d love to wear a gorgeous pair of 3” heels. I notice you sometimes wear high heels…..I wish I were so confident! How do you do wear them so gracefully! Should I just grow a thick skin and wear some and stare down the snarky comments? Thanks


Wednesday 27th of July 2022

I like the mules you featured! I’ve never worn mules before. How are they for walking around? I can see them for wear at a desk type job, but would they be good for someone on their feet most of they day, like a teacher? Thank you!


Wednesday 27th of July 2022

@Megan Kristel, thank you for responding! That extra advice was really helpful!

Megan Kristel

Wednesday 27th of July 2022

Hey Jennifer, the fit and comfort really depends on the shoe you buy and your foot, BUT, I do like this particular pair. And for any mule you go with, pick up a pack of Foot Petals. They have a product called Tip Toes that help keep the shoe on your foot and also a Gel Under Hell Cushion that gives a little more support for your arch over the course of the day.

Tracy Gray

Wednesday 27th of July 2022

Love the blazer! Perfect for fall and winter!!

Megan Kristel

Wednesday 27th of July 2022

Right!? And such a great price! xx

Bonnie Davis

Wednesday 27th of July 2022

I found this post very helpful so thank you! 😊 I can always use ideas related to how to use an item of clothing in multiple ways as I tend to get stuck in a rut.

Just a quick question: as a rule, do you recommend spending more on shoes and handbags, then saving on jeans/pants, dresses or tops?

Megan Kristel

Wednesday 27th of July 2022

Great question. I suggest buying the best you can afford on items you wear frequently and items that are a fit issue. Shoes would be a good example because generally speaking comfort/style/quality comes at a price. But this is of course a guideline and not a rule. This article breaks down our thoughts: Where to Splurge, Spend and Save