A picture is worth a thousand words, no? What about these four pictures?

The obvious part of the collage is that Laura is wearing the same blue button down in each of the outfits- we love an outfit repeater. But what haunts me about these images is the of said button up; it’s perfection.

In the last year or two I’ve been dedicated to the quest to find a button up that fits JUST right. There is a particular way that button downs are worn that make me want to scream with glee. And not just Laura’s. Of course, I have the receipt to prove it.

The Olsen’s know how to wear ‘em;

Zoe Kravitz kills it;

J.Law looks great in them;

Charlize Theron nailed it;

I purposefully picked these photos because not only do these button up shirts look amazing; but they are being worn in real ways. These pictures are not staged photos where the outfit only looks good when we are contorting our body to get the shot. No, this button- up fits like a dream as the wearer walks down the street to grab a coffee.

My inspiration photos do show these button downs in a more setting but my investigation isn’t limited to that. Oh no, I think the tips I discovered are just as relevant for those among us who need to tuck our shirts in and wear them into a slightly more formal space.

BUT- as a warning- this is not your manager’s button up. This is not going to be the button up you wear into a job interview or for a major presentation. These are button ups that give an easy-breezy-chic (EBC) vibe.

And I KNOW we are all invested in this because my internet friend

posted this note and the response is; YES! How do we get a button down to fit well?

As a note; a button- DOWN is a shirt that has small buttons on the collar to keep it in place. Mostly I am looking at button- UP shirts which have no buttons on the collar. Honestly, in my brain I still think of them as button-downs but that is technically inaccurate so I’m going to do my best to call them button ups.

There are really 2 key pieces in finding a button up that gives us the EBC vibe and those are; (1) MATERIAL and (2) FIT. And, obviously, some observations on STYLING.

The very best button up shirt is going to be worn in. Sorry, I said it. Luckily button ups abound at literally every single thrift store (walk straight to the men’s section, I’ll get into this more when I talk about fit, but men’s shirts will give you the fit we are after) and you can find them for $3-$15 easily! Assuming you are buying a shirt that has been worn and washed, you may not have to pay attention to material as much since the shirt has probably softened.

BUT if you are shopping new; here’s the scoop in terms of material; what we are *really* after is a loose(r) weave and, preferably a natural fiber! The looser the weave the softer and more breathable the fabric will be, giving us drape and movement! The weave of any natural fiber will soften with wear/wash hence the call to shop second-hand. Stiff, starched or heavy fabrics aren’t going to give us the look we are after.

The fit is where I, historically, went REALLY wrong when buying button up shirts. I blame my millennial roots wherein the epitome of J.Crew style was a very-fitted button up.

But even Jenna Lyons knows that now we wear our shirts oversized.

So, if you are a millenial or older, we have to start by buying a shirt that feels BIG. As I mentioned before, shopping second-hand in the men’s section will get you really lovely, soft shirts AND provide you with the oversized fit we are after.

Nowadays, most women’s shirts are cut more generously now so I’m not going to say that you need to size up per se. But there are a few fit details we are after that will help guide you in picking a good size;

Ok, so you’ve bought a shirt in the fabric and fit that you love BUT now what?! I have a great button down but have struggled with how oversized it is (see here for more on that!). It’s not lost on me that Laura Harrier (whose pictures I began this post with) is 5’9” and a literal model. BUT I also included pictures of Zoe Kravitz and the Olsen girls because they are petite and still pull off the oversized look so well.

No matter your height or size, the first styling tip is crucial to capture the EBC (easy-breezy-chic) vibe. Interestingly I JUST wrote about it in my blazers post as well which proves it’s really the universal tip.

Look at any photo of an oversized shirt and you’ll notice the sleeves are rolled or pushed up (often all the way to the elbow!). It doesn’t HAVE to be fancy;

Or you can do the CLASSIC J.Crew cuff made famous by Jenna Lyons back in the day. This photo shows the cuff on a slim fitting shirt but it looks equally good on an oversized top.

Because I have a casual lifestyle, I usually choose the lowest button that I’m comfortable with to create a at the top of the shirt and then I button 2-3 buttons (or to the point that meets the top of my pants. This allows me to open the color and show some skin at my neck AND allow for more movement at the bottom of the shirt when I’m walking.

But here’s the real sticky part of styling your button down because you’ll need to find what feels right to you in terms of tucking your shirt.

Personally, I like having SOME visibility on my waist, I just like the way I look better. AND since I cannot walk around all day with my hand in my pocket, I have most studiously looked at we are tucking our oversized shirts.

Firstly, there’s the full tuck and certainly what is best for a formal setting. Because we are talking about oversized shirts, there is often a lot more fabric to tuck in and that’s not always comfortable. You may want to aim for a shorter shirt if this is your desired styling.

OR you could do the where you take the front half of your shirt, stopping at the venting seam, and tuck that into the front of your pants and leave the rest out. I LOVE this option but, friends, I think we are living in an episode of Black Mirror because, I swear, evidence of this styling has vanquished from the internet. Because I love you all so much, I decided to show you myself. I really don’t love video so I turned myself into a GIF (once a gif, always a gif).

You can do a , which Gen Z (and the internet powers that be) seem to approve of more because I could find pictures of it. For this tuck you want to take the button-side of the shirt (the side closer to your body) and only tuck that in leaving the hole side to be lose in front.

BUT I saved the best for last!! My new personal favorite hack is the ! I might be late to this party but I just learned how to do it and now I see it everywhere! It gives the perfect visibility to the waist while maintaining the EBC (easy-breezy-chic) I want.

The diagonal tuck goes like so;

You are taking the corner of the button edge and tucking it at the waistband on the side of your body to create a diagonal drape in the tuck. There you go! You get the waist and pocket exposure without having to pose all day long.

PHEW! SS is already telling me this post is too long for email! However I have genuinely been clicking on EVERY single link for a button up that I see over the last year and I compiled a list of the most recommended button ups here. After lots of field research, I’m telling you that the Gap Big Shirt is TOP of the list. They sell it in Poplin and Oxford (both materials, if you recall, which will get better and better with use!).

Recently, I, myself, was influenced by

with this button up ($138). I sized up one size to create some volume in the sleeves and it’s a truly perfect EBC shirt in looser weave cotton that- I think- also looks great tucked in or worn more formally.