Spring/Summer Fashion
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How to Wear An Oversized Button-Up Shirt

Happy Friday, friends! We’re wrapping up our second week of 23 Days of Spring Fashion, and today I want to talk about how to wear an oversized button-up shirt — one of the biggest fashion trends for spring 2021.

Jo-Lynne Shane styling an oversized button-up shirt with white jeans and booties for spring 2021wearing: pinstriped shirt (50% off) // Paige Hoxton skinnies // booties // leather hobo (50% off) // hoops // necklace // bracelet

While a button-up shirt is a wardrobe staple for many women, this year’s version is bigger and bolder and more relaxed. I was drawn to this pinstriped tunic shirt because it plays to the current oversized trend, but it has a slimmer silhouette than most.

Jo-Lynne Shane wearing an oversized button-up shirt with white jeans

It’s also made of a lovely lightweight and soft 100% cotton fabric that has a bit of a drape and feels really nice against the skin. It looks polished yet effortlessly casual, and it pairs perfectly with white denim.

This shirt runs true to size (I have the small) and it’s currently 50% off with code  SPRING.

Jo-Lynne Shane styling an oversized button-up shirt with white jeans and booties for spring 2021

A few tips for styling an oversized button-up shirt — always cuff or push up the sleeves, weather permitting. Cuffing makes a tailored shirt look more lived-in and relaxed.

I just rolled mine twice, but it’s more chic to do a stylist’s cuff. I really need to try that sometime.

And it’s very of the moment to half-tuck the front of your button-up shirt, or knot the one side. I tried both of these methods in the pictures below.

 

While I can appreciate these styling techniques on others, I feel more true to myself with this shirt left hanging, so that’s what I did.

I also prefer this style of shirt with a skinny jean, to help offset the volume on top, although it’s very on trend right now to wear these shirts with relaxed trousers for more fluid lines.

At the end of the day, individual style comes from being true to yourself, and I really like the simplicity of this outfit the way I styled it here, untucked over white skinny jeans.

How to Wear An Oversized Button-Up Shirt for Women Over 40

The booties are a little unexpected for spring, but this light bone color makes them a nice transition shoe for those of us who live in colder climates. I’ve had these for a while, and they’re low inventory, but perhaps you have something similar.

I also carried this leather hobo, and it’s part of the Banana Republic Friends & Family Event, so you can get it for 50% off now through Sunday. It’s a really soft pebbled leather, and it has a bit of slouch without being too large and in charge.

When the weather gets warmer, and as another option for those of you in warmer climates, I also shot this look with these ivory braided sandals and my Tory Burch McGraw hobo.

Unfortunately, these sandals are selling out quickly, but you can find them in limited sizes at Zappo’s, Nordstrom, Bloomies and Dolce Vita’s website.

How to Wear An Oversized Button-Up Shirt

I love the braided straps, the square toe, and the croc-embossed leather covered block heel. They also come in a really cool tobacco color.

I’m wearing my usual size 8, but I could definitely have sized down half, as I typically do with slides. It’s me, not the shoes. For ladies with typical arches and medium or wide-width feet, I recommend going with your true size.

For accessories, I wore the gold hoops from Anthro that I’ve been featuring a lot lately and that double chain necklace I picked up at Evereve. I also added this delicate snake wrap bracelet.

The contrast of the gold jewelry against the cool tones of this simple outfit is really pleasing to the eye and helps keep it fresh.

How to Wear An Oversized Button-Up Shirt for Spring

Be sure to visit Cyndi Spivey and see the spring look she’s styling today!

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photos: Alison Cornell

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48 thoughts on “How to Wear An Oversized Button-Up Shirt

  1. I really like this outfit on you! It looks sophisticated yet very relaxed & carefree, all at the same time. I can also envision how good the oversized top would look with a more relaxed pair of pants. I bet that top would be just as cool, if not more so, than a regular top because it allows air to circulate. Other than our usual nightly bonfires, we don’t have anything exciting going on this weekend. Doesn’t it feel good to have your closet changed out, ready for the new season! Oh, don’t forget to change the clocks Saturday night before going to bed.

  2. And today I see comments without doing a thing! Bizarre. Hopefully it means things are working for everyone now.

  3. Right before I opened your email this morning I was thinking that I should think about a way to wear my oversized gingham button up for Spring, and there was my answer! Appreciate the fun styling tips for the cuffs and tails of the shirt but I prefer the way you styled it. The knotting one side definitely looks a bit “tried too hard” for me. I may add a white tank to peek out the top for added warmth. Thanks for the ideas!

  4. I’m always in awe of you doing you closet clean out in a day and without emotional issues! Lol! But then I remember you do this professionally! I am inspired to start this though, really tired of winter clothes. I love the button up style and plan on looking for the right one for my plus size apple body. Thanks for all your inspiration!

  5. I almost bought a similar shirt at Chico’s in petite but the only way I could think of styling it would be with white jeans. Looks cute so maybe I’ll go back for it.

  6. I have been trying to get on board with the button-up, but I don’t love it on me. Even with skinny jeans, I feel a little dumpy. I think it’s the length of the shirts. I’ve started packing away my winter clothes, too. I know it’s still technically winter, but mid-March I start packing away most of my dark colors, including my dark jeans. I have a couple of light-colored sweaters, which I keep out but the wool and cashmere (except for my short-sleeve Everlane cashmere) get packed away. Winter shoes, too. I have big plans for the weekend! Coffee with a friend, outside if it’s warm enough Saturday and I’m taking my grandson to baseball practice!

  7. Love a light, flowy button UP shirt!! Thank you for showing the front/side tuck, and that side knot was interesting! I would probably try the full knot with both sides, that always works for me to contain a billowy shirt! 🙂 Looks like this shirt is longer in the back, wish you would’ve shown that angle. It would also be great, unbuttoned, as a very light jacket with a navy tank underneath. Love the white jeans, too, very spring-y!

  8. Hello! I love the look on you but I’m not sure I like being able to see your pants through the shirt. It cuts me in half….when I wear that lighter fabric. Any suggestions?

  9. Such a great classic look, love this on you JoLynne! I love a good button up, just hate to iron haha. Love the way to styled it straight, not so much for the half knot or tuck but that’s just me. Maybe tie both in front would be cute with shorts. Thanks for all the tips and you are, as always, so thorough with your review, thank you!! Have a wonderful weekend. 🙂

  10. Love this look and have been wearing it for years as it’s my style. I always like to wear a cami with a built in bra for comfort and modesty. I agree with you on skinny jeans with this look to balance out the volume of the blouse 😉

  11. Is this shirt really thin? It seems you can see the top of your jeans through the shirt. On the front, the pockets provide coverage but on the back is it more see through?

  12. I was surprised how slender you looked when I scrolled to the first picture, never thought an oversized shirt could do that! When I clicked on link to order it shows the only color option as white, is that the color of yours?

  13. This shirt style is my absolute favorite! The color of this one is so pretty. Do you think it’s too long wear with shorts? A button up shirt and shorts is my summer uniform 🙂

  14. Jo-Lynne! 👏🏻 You have been speaking directly to me the last few days. The sweatshirt dress, black blazer outfit, and now the button down shirt outfit are the styles that I find most flattering. Old Navy offers similar button downs of decent quality. The stores also sell a cute pointy toe light beige flat that works well with the outfit you featured today. Ankle length pants look super cute with the shirt and flats. Look forward to seeing your next fashion post!

  15. Jo-lynne YOU LOOK ADORABLE AS USUAL! I WANTED TO SEE IF YOUR BLOG TEAM HAS A COUPLE OF ITEMS ON THE FIX IT LIST. ALL OF THESE ARE HAPPENING ON IPAD: 1) IF YOU CLICK ON THE # COMMENTS AT THE TOP OF A POST, NOTHING HAPPENS. IT DOESN’T TAKE YOU TO THE LIST OF COMMENTS LIKE IT SHOULD. 2) YOU STILL HAVE TO CLICK “LEAVE A COMMENT” AT THE BOTTOM IN ORDER FOR THE COMMENTS TO SHOW UP, OTHERWISE YOU DON’T SEE ANYTHING. 3) ONCE YOU DO CLICK LEAVE A COMMENT, IF YOU GO BACK UP TO THE TOP AND CLICK ON THE # OF COMMENTS LINK AGAIN, IT WORKS CORRECTLY AND DROPS YOU BACK DOWN TO THE LIST OF COMMENTS. I’VE TESTED THIS A FEW TIMES AND IT BEHAVES THE SAME EACH TIME. 4) LASTLY, WHEN LEAVING A COMMENT USING AN IPAD, THE TEXT IS STILL IN ALL CAPS LIKE IT USED TO BE PREVIOUSLY FOR MOBILE. HOPE THIS HELPS AND I SURE LOVE YOUR CONTENT – IT’S SO FUN TO WAKE UP TO EVERY DAY (I’M IN WASHINGTON SO YOUR POSTS ARE TYPICALLY UP WHEN I WAKE UP, YEAH!)

  16. Love this look! And I too just like it hanging outside a skinny Jean.. I’ve started going through my spring and summer bins.. I’ve moved a few spring items into the closet and took out a lot of warmer winter items, but I like your idea about leaving just a few of my go to sweaters 🤔.. it’s 56 today and sunny but we are going back to cold weather next week! I’ll enjoy it while cuts here! Attending a baby shower this weekend… now that’s something I haven’t done in a long time.. we are going in shifts to keep the numbers small …

  17. I love this outfit. I assume you got the small in the shirt. Both views, with the booties and the sandals is so clean and fresh looking, but prefer the sandals. the purse at Banana looks gray not beige or the color of your bag. I did my closet yesterday too and feel like I could throw out 80% of it. Nothing looks right anymore and since I didn’t wear hardly anything there, maybe I should toss it all.

    1. Penny, I am currently reading Project 333 by Courtney Carver and it is wonderful. Even if you don’t attempt the 333 challenge (wear only 33 items for 3 months) the closet clean-out suggestions are really helpful.

  18. What method/company do you use when you sell prior season clothing? I’ve thought about doing with purses I ended up barely or never using but wasn’t sure of the best option.

    1. I always recommend Clothes Mentor or Style Encore – they pay you on the spot for what they keep. Then they will either give you back the rest or donate it for you.

  19. I think this is the first time that I have seen you in a buttoned shirt, Jo-Lynne, but it looks very nice on you! Definitely a casual, lived-in vibe.

  20. Your outfit looks so great on you! I have something similar and now I’m excited to try it. Looks like your blog is all set and working! Now you can just have fun with it.😊

  21. Love this outfit and super love the shoes! They’re mostly sold out at BloomingdaleS and Zappos so I went to Dolce aVita’s webs and they’re backordered until May 14! 😩

  22. I really like this loose button-down shirt look! And I was wondering what sunglasses you’re wearing? They’re great 🙂

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