How To Wear A Button Down Shirt This Fall

It’s hard to think of a wardrobe item that could be considered more classic than a white button down shirt. And before we dive in, let’s address a quick debate. Is it button down shirt? Or button up shirt?

I would also consider a classic white shirt to be the only clothing item that can stand alone as a Halloween costume. Think Tom Cruise in Risky Business – a white dress shirt plus tube socks and sunglasses and you are good to go!

I’ve owned a lot of white dress shirts over the years. For the longest time I struggled to find one that was tapered properly for my narrow frame. I just felt like it would swallow me whole. Then I did find some that were more feminine cut, but then it felt like it lost its chrispness.

So, thanks to my trial and error I have finally determined that the ideal white button down shirt for women is one that is proportional but not fitted. This way it’s still feels and looks classic but isn’t completely unflattering.

The one I am wearing here is from the company UNTUCKit (UNTUCKit $78). I want to say I first saw them on Shark Tank and kind of guffawed at what a simple concept the brand was – same old shirts the perfect length for not tucking in. Someone gave me a gift card to the site and I treated Kevin to a few men’s shirts and snagged this “Jackie” style for myself. I will say they are in-fact the perfect length to wear without tucking in. I guess they nailed it!

It is also wrinkle-resistant and MACHINE WASHABLE which is a huge adult win. Nothing is more demoralizing than steaming or ironing a garment and then sitting down for two seconds only to undo all of that effort. I don’t think the shirt is perfect in that sense, but it does take a lot more to be so wrinkly it is unwearable.

Side note – your white shirt should also be thick enough that you cannot see a bra or undershirt underneath. That alone will make your vibe look way sloppier and less quality.

Here’s Four Ways To Wear… plus, a bonus look!

This is the easiest way to wear as far as number of pieces involved. Wear your white button down shirt as it’s meant to be worn and pair it with leggings and boots or booties. Because there is very little structure in the top half of this outfit, I went with sock booties to keep my bottom half tight for balance.

I would suggest pairing with a structured purse to, again, add shape where there is none.

A little less dressy than the previous option, but still chic all the same. This time grab skinny jeans and your favorite knee-high boots for the bottom half. Coordinate that with a long line chunky sweater of your choosing. I didn’t happen to have a chunky enough sweater in a bright color or a pattern but I would highly recommend going that direction instead of a neutral.

I am only suggesting that because that is a lot of neutrals for one outfit and you know I can’t be too basic for too long.

OMG This is my favorite one! As you know, I’m already obsessed with these $30 jeans from Target. I did a whole article about how to wear them here if you need a refresher. I tucked in the front of the shirt and let the back hang out so it didn’t feel too stuffy.

I wore nude pumps here, but quite literally ANY shoe will do. Even some slim-line sneakers would work here and still feel appropriate with this top.

And now for something totally different! I saw a cast member from one of my favorite Bravo shows (Summer House – hey, Amanda!) wear a button down shirt like this once and I’ve not forgotten it. Hers was leopard, but still the same effect.

Unbutton the shirt enough to be able to drape it over your shoulders. This will mean the front will be way shorter than normal, so you absolutely MUST pair it with something high waist. Otherwise it will be all weird and baggy where you don’t want it to be.

This is my wildcard look – what do you think? Does it work or does it flop?