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How to Wear J.Crew Factory’s Flannel Shirt

Of all the “Outlet” brand retailers, J.Crew Factory is the only one I frequent. 

I have a lot of luck with many of their styles and I appreciate the extensive size range. Plus, for me, there is one right next to my local Whole Foods, so a quick pop-in is easy, though lately, I find their online options 1000% better than what’s in the store.

We featured this plaid button-down in our Sunday Sales round-up this past weekend, and it was no surprise to see it on the best seller list.

This particular color-way stood out for it’s depth and versatility. Today, I’m using it as a neutral pattern and layering in some other best selling items from the past few weeks, creating two looks you can start to wear the second it gets chilly. 

So let’s jump in, because there are a lot of tips and options to cover. 

Create Your Base

Navy Flannel Shirt and Dark Slim Straight Jeans

Flannel Shirt, $46| Slim Straight Jeans, $40  Plus 25% off with Code BONUS


We’ve talked before about creating a column of color to act as a base for your outfit.

So, for example, you take a black tank and pair it with your black pants, and then you can add all sorts of jackets and layers on top.

The column then helps to elongate the line of your body. I didn’t make this up; it’s a well-known dressing tip;).

Above, we’re doing something similar, but pulling out the dominant color in the shirt, in this case, navy, and pairing it with dark wash jeans. 

The look is cohesive and makes for the perfect base to add some of your favorite fall layers. Plus, it’s inexpensive. The shirt is under $50 in regular and petite, in XXS – 3X and the jeans are a go-to from Old Navy for $30 in regular, tall and petite in 00 – 30. 

Now let’s add those layers. 

How to Wear J.Crew Factory’s Flannel Shirt

Navy Flannel Shirt and Dark Slim Straight Jeans, ivory shacket, tan suede booties, tan leather mini bag, gold layered initial necklace or Navy Flannel Shirt, Dark Slim Straight Jeans, Black Leather Hobo Bag, Black Chelsea Boots, Navy Quilted Vest, and gold chunky necklace

Remember, our How to Wear it posts are both instructional and inspirational. 

We use previously featured, popular item from recent posts to show you how, with a little thoughtfulness, your wardrobe really can mix and match beautifully. 

So you know, if you purchase something through one of our links, it will likely pop-up over and again in our content throughout the season. 

With a Puffy Vest

Navy Flannel Shirt, Dark Slim Straight Jeans, Black Leather Hobo Bag, Black Chelsea Boots, Navy Quilted Vest, and gold chunky necklace

Quilted Vest, $114 | Chelsea Boot, $70 | Chunky Chain Necklace, $34 |Leather Hobo Bag, $118 

We’re starting with another best selling item from last week, the J.Crew Excursion Quilted Vest

Readers loved the nutmeg, black and navy options. Here, we’re using navy, to create a monochromatic look. The nutmeg wold look great here too. 

Then, grab you Chelsea Boots. You may have a pair from last year, or this pair from Amazon’s The Drop Collection, ,or, maybe you picked up this under $100 pair from Caslon at Nordstrom, also featured on Sunday

Any pair works here.

And stay tuned because tomorrow we feature the Chelsea Boot in our Outfit Formulas, and go into more styling details. 

For this look, I’m using the Caslon option

What’s important is understanding the need for balance when wearing a chunky boot. We do that here with the vest. You could also add a field jacket, or an oversized scarf/wrap. 

Then, accessories, like this popular inexpensive gold-tone chain to fill in your neckline.

And for a bag, a slim hobo, like this very reasonably priced option from Madewell. 

With a Shacket

Navy Flannel Shirt and Dark Slim Straight Jeans, ivory shacket, tan suede booties, tan leather mini bag, gold layered initial necklace


Shacket, $80 | Suede Bootie, $285 | Layered Initial Necklace, $15| Compact Mini Bag, $180

I love that by just swapping out a few pieces, we can make a different look.

First, I have a lot of opinions about shackets, mainly they make me look like the Brawny man.

Often done in oversized plaids and boxy silhouettes, they tend to lack feminine shape, so be careful if that is what you are going for.

Especially if you are broad or have a large bust, you may not like how these look on you.

There are, of course, exceptions. Something like this brushed-cotton Shacket at Old Navy, also 25% off with Code BONUS, is a nice option. 

It’s a slimmer cut, I would size down if you are in between sizes, and makes a great top layer. 

For boots, you can wear your favorite ankle boot, in a tan or cognac color. Here, we’re using the AGL suede boots, an investment, but still on sale

Add a fun and inexpensive layered necklace, like this initial letter gold-tone option from Amazon and this mini crossbody by Frame on sale over on Shopbop.

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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 J.Crew Factory\'s Flannel Shirt

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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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Friday 16th of September 2022

Question. Do you tuck the flannel in or leave out? Especially if layering a vest