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How to Wear a Classic Blue Button-Down

Have a classic light blue button-down in your closet?

Or maybe you picked up the blue pinstripe version from J.Crew featured on Monday?

Grab it, and let’s make some outfits!

You can wear a top like this a million ways, but today, we’re going to talk about three ways to style it.

How to Wear a Classic Blue Button-Down

Three outfits featuring a blue button down shirt

As always, today’s post is made up of items we’ve previously featured, along with new ones in inclusive sizes so please see where I make a note. 

Going forward this year, since it’s currently January, I’m going to showcase looks that can be worn in the cold weather and also transition into Spring. 


Classic-fit Washed Cotton Poplin Shirt 

J.Crew Blue Pinstripe Button Down


Classic Button-Down, $79.50 Available in sizes 0 – 24.

In the looks below, I’m working with the classic-fit washed cotton poplin shirt in pinstripe from J.Crew. I like this particular shirt for a few reasons.

First, it comes in all sizes, so you can play around with the fit. If you are busty or wider in the torso, try sizing up.

They call it “washed” because it looks a little lived-in, which I love, especially when paired with more polished, tailored pieces. 

If you prefer a crisper look, you can wear something more traditional at a similar price point like this Foxcroft non-iron oxford in regular sizes here and plus here.  

Layered Neutrals

Blue Button Down, tan wide leg trousers, tan woven bag, tan suede pumps, tortoise sunglasses, and chunk gold chain necklace

Creased Pants, $35 | Suede Pump, $60 | Woven Tote, $88 | Chain Necklace, $24 | Tortoise Sunglasses, $28 

I want to dive headfirst into this look.

NOTHING makes my style heart sing like layering a variety of neutrals in different hues and textures. 

Here, I started with, wait for it, wide-leg full-length trousers

These are from H&M, for only $35, available in sizes 0 – 20. You want these long, with the hem puddling on top of your shoe, so alterations will be needed. 

Please don’t avoid purchases that require tailoring. If you are, it’s one of the reasons you have nothing to wear. 

You might need the hem taken up, or, sometimes in my case (I’m 5’10), taken down a bit. But, it’s an easy and affordable adjustment. 

Because the pants are long and have a crease down the front, you need an equally elongating shoe. 

I’m using these Linea Paolo pumps in tan suede, on sale at Nordstrom Rack for $60. You can also use the heels featured in our third look below by Marc Fisher. 

Just remember you need a heel and a pointed toe. 

This woven tan tote is STUNNING and adds so much dimension and personality to the look. It’s by Aqua and only available at Bloomingdale’s for $88

For accessories, I went to Tuckernuck.

I scooped up this oversized necklace I featured in Sunday Sales this weekend and cannot wait for it to get here. Layer it under the collar of your shirts or over sweaters. 

They also have a fantastic selection of fashionable sunglasses at low prices. For example, the tortoise pair featured above is only $28

The New Casual

Blue Button Down, straight leg jeans, tan crossbody bag, white sneakers, and blue coat

Straight Jeans, $128 | Coat, $70 | Sneakers, $118 | Crossbody Bag, $115 

I love this look so much I went ahead and ordered everything I didn’t already own because pairing sporty pieces with chic details is my favorite new trend.

Let’s start with jeans. Madewell makes a solid casual jean option in regular, petite, plus and tall sizes. I own and wear these frequently. You can see them here in a look I wore very similar to above

I get a lot of friendly push back on a jean that stops around your ankle and am often asked if I get cold with my ankles exposed, so I want to note I wouldn’t wear them in the snow or below freezing weather 🙂 

You can easily swap them out for whatever style of jeans you prefer. The ankle length just lets you play with different proportions. 

Next up, H&M is a wonderful resource of affordable statement coats. I couldn’t pass up this gorgeous oversized blue option for $70. I’ll also throw it over an all-black turtleneck and pant combo and even over a matching sweatsuit. 

For shoes, I landed on these by Veronica Beard for sneakers, deeply discounted (originally $295, now $118), and bought them right away.

I can’t speak to the comfort just yet, but they look so chic, and the savings are fabulous, so fingers crossed. They have a few recent reviews that are all positive. 

Then a crossbody bag with similar woven detail again adds layers and interest. The contrast of the sporty bag and the oversized coat keeps the look balanced and gives a playful feel.

Back to Work

Blue Button Down, navy ponte skirt, large navy leather tote, tan suede block heel pumps, and pearl stud earrings

Ponte Skirt, $85 | Zipper Tote, $225 | Block Heel Pump, $160 | Pearl Stud Earrings, $65 

Remember traditional workwear? 

Despite what we see online, many women still go to the office and need to dress professionally. 

Since it’s winter on the East Coast and currently freezing, the last thing I think to grab is a skirt. But, if you are working in an office and need some variety in milder weather, a navy pencil skirt is a must-have

And they are not easy to find these days! However, Boden makes a lovely option, available in navy and black, in sizes 2 -22, in regular and petite sizes for $85. 

You want the hem of the skirt to hit you at the top to 1″ above your knee.

Tuck the shirt into the waistband; you can make this look as polished or casual as you like.

And if you want to add an extra layer like a blazer or cardigan, you certainly can. I like the look either way. 

For accessories, you have a lot of options. 

I went with this navy tote from Cuyana. It’s high-quality leather, with a convenient and rare top zip that will hold all of your essentials. Available in a ton of color options. 

And for shoes, I ended up with these block heels from Marc Fisher, a modern version of a classic pump. They come in tan suede and cognac suede, use the neutral closest to your skin tone to extend the line of your leg. 

If you wanted to add a pop of pattern, wear your favorite leopard print heels. 😉

Finally, an affordable pair of wear-with-everything updated pearl studs for $65.

How to Wear a Classic Blue Button-Down

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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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Lesley Revuelto

Wednesday 19th of January 2022

I love this series! Taking one piece and then creating three outfits. When I purchase something, I try to see if I have 3 things at home that I can wear with it. You’re making it too easy to shop😂

Megan Kristel

Wednesday 19th of January 2022

Thanks Lesley! It's really the best way to make sure you get value out of what you are buying. I'm so glad these are helpful!