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Four Ways to Style a Button-Up

Four Ways to Style a Button-Up

Button-ups are a closet staple — it’s so easy to pair them with jeans and call it a day. But what if you want to make the look a little more exciting? And shake up your outfits a little? We asked the genius stylist, Lisa Fine, to give us a few outfit ideas for fall…

OUTFIT #1
Four Ways to Style a Button-Up

Our friend and model Natasha Janardan with stylist Lisa Fine.

Lisa’s styling tip: Layer, layer, layer. “The best way to dress up a T-shirt and jeans is a patterned button-up,” she says.

Four Ways to Style a Button-Up

For this look, tuck a tee into high-waisted jeans, then layer with an unbuttoned, slightly oversized striped or plaid shirt. Add sneakers and a trench; tie the belt in the back to open up the coat, and pull the shirt’s sleeves down (so you can see a little more than just the cuff). Then scrunch all the sleeves up. Voila! A fall uniform.

OUTFIT #2
Four Ways to Style a Button-Up

Lisa’s styling tip: Go monochrome. “The easiest way to look thoughtful is to wear a monochromatic outfit,” she told us. “Even a sweater and sweatpants in the same color looks cool and intentional.”

Four Ways to Style a Button-Up

Lisa paired a slouchy blouse, wide-leg trousers and a crossbody bag in a similar blush shade, but tied the look together with a bolder heel. If you’d like to play with proportions, roll the sleeves of the blouse up, or do a half-tuck with the shirt. So cute, right? We’d also love to try this look with other colors, like a white button-up and white ankle jeans; or even just chambray and denim.

OUTFIT #3
Four Ways to Style a Button-Up

Lisa’s styling tip: Experiment with contrasting styles. “I like an unusual style opportunity,” Lisa says.

Four Ways to Style a Button-Up

For this outfit, Lisa layered a feminine ruffled shirt under utility overalls. “It works because the pieces balance each other out,” she explains. “Just be sure to show a little skin when wearing so much fabric — for example, unbutton the top and roll the ankle.”

OUTFIT #4
Four Ways to Style a Button-Up

Lisa’s styling tip: Transition your summer wardrobe. “You can wear off-the-shoulder tops in the fall by layering a button-up underneath. You’re also refined and covered enough for an office,” says Lisa.

Four Ways to Style a Button-Up

Here, Lisa styled an off-the-shoulder tee over a woven shirt, and paired them with a paperbag skirt and loafers. “To get the shirt to layer properly, pull it down from underneath the skirt,” she adds.

Four Ways to Style a Button-Up

Thoughts? Which would you wear? Thank you so much, Lisa!

P.S. Lisa’s week of outfits.

(Photos by Christine Han for Cup of Jo. Thanks to our friend Natasha Janardan for modeling. This post is sponsored by Nordstrom, a retailer we have loved for years. Plus, they always offer free shipping and free returns. Thank you so much for supporting the brands that support Cup of Jo.)

  1. Joie Gahum says...

    I found a really good button up shirt in Cicihot so I got it. I had troubles on matching it because it was my first time having. Thanks to you for the ideas!

  2. Alexandra Marie says...

    Love that monochrome pink outfit! I would have paired it with the cognac suede day heels from Everlane. Love that shade of brown and pink together, and I think it grounds it a bit more for fall.

  3. the blush outfit gives me so much inspiration, especially for end of summer//early fall.

  4. Lane says...

    I think these are the sort of outfits that our children will all look back on in 15-20 years and think, “Dear God, did my mom actually wear that?”

    • Joanna Goddard says...

      haha, yes, that’s always true with anything even slightly fashion-forward! also i think birkenstocks will look terrible in hindsight, even though i love them now :)

  5. Liz says...

    your model is beautiful!

    • Annie says...

      my thoughts too, her face is like sunshine

  6. Haylie says...

    I *love* monochrome outfits (especially with kicky shoes). This blush pink outfit, with that gorgeous lipstick, is killing me.

  7. Such creative tips. That blush pink top is to die for!

  8. Andrea says...

    Button ups have always been a major fail for me. I have a small chest, yet they gap, and they make me look so mannish. Not a look I’m going for.

    • Jean says...

      I used to feel the same way! But then I started unbuttoning them so my bra shows a bit, and I got a bra (from Target!) with a little ruffle that almost looks like a camisole when it shows. No chest, but definitely not manly. ;)

  9. Zoë Chan says...

    What brand is Lisa’s pair of jeans?

  10. Laura says...

    She’s adorable.

  11. Amy says...

    Guess I’m in the minority on this one. Pushing up a double layer of sleeves…super uncomfortable. A woven shirt under a thin knit…you see the bumps of folds and buttons. It’s rare, but none of these struck a cord with me. Vive la difference, I guess!

    • Meghan Edwards says...

      Same

    • Laura M says...

      I agree, I wouldn’t like any of these looks on me or anyone else. Maybe it’s an age thing but I think clothes should make you look good, not weird.

    • Polly Hitchcock Sage says...

      Ha, I really can’t stand the idea and the reality of having to wear 2 shirts ever. I just won’t wear it. There is no point. Yes, I wear sweaters, but I agree, wrestling with skinny knits and a stiff shirt didn’t sound fun.

    • CJ says...

      I’m with you. I think you can get away with this in a more fashion forward city. Two shirts sounds like my worst nightmare. I couldn’t pull it off. Get it?

  12. Emma says...

    I love posts like this because they help me reimagine what I already own instead of feeling the needs to buy more. I am now inspired to create new outfits out of existing items. Perfect.

  13. Roselyn says...

    Any word on what stunning lip color she has on? It’s SUCH a beautiful pink.

    • Stella Blackmon says...

      Hi Roselyn!

      Her nude color is a Topshop lipstick in ‘Devotion’: http://bit.ly/2uM7peF

      Her orange-y color is NARS in ‘Lana’: http://bit.ly/2v4SDen

      Hope this helps!! :)

  14. justine says...

    This may be one of my all-time favorite style posts yet! I love each outfit and LOVE the styling tip for off the shoulder tops … i hate a strapless bra, so may use that trick for multiple seasons. I’m thinking a front racerback tank with off the should would be cute also!

  15. Celeste says...

    I am *loving* that last look so much! I haven’t bought any off-the-shoulder sweaters or shirts because I pretty much only buy tops I can wear at home or in the office, but now I’m convinced it’s a great twist on the classic button down/sweater combo. Fantastic look.

  16. Carly says...

    I bookmarked Lisa’s “week of outfits” when you first posted it and consistently revisit it because I loved her style so much- so fun to see her work her magic with Fall pieces!

  17. Kristin says...

    So funny – where I live (northern Midwest) we call them button-downs!

    • I’m on the east coast of Canada- it’s button downs all the way! ‘Button up’ sounds so prudish! Haha…

    • Cazmina says...

      In Australia we just call them shirts!

  18. Amy says...

    I actually bought my first casual – non-stiff, patterned button up two days ago so this article couldn’t be more perfect in timing.

  19. Mette says...

    Thanks, as always for displaying models of different shapes and ethnicities. Such a beauty, and great styles too!

  20. Stephanie says...

    I like these ideas! Any good button up recommendations for a larger chest, however? It’s difficult for me to find an option that *fits*.

    • Jenna says...

      I feel you on this! I have had luck buying my shirt a bit bigger and getting it tailored. Also, safety pins between the buttons are your best friend. I put them in from behind and make sure they don’t show by only pinning the first layer of fabric.

  21. I LOVE the look at the ruffled blouse under the overalls! I’ve been wanting to try the high neck ruffled blouses, but I feel they’re a little too formal for my stay at home mom – preschool dropoff life lol. But here in France the everyday style is a mixture of casual elegance, so this looks truly perfect. Great post!

    Xoxo http://www.touchofcurl.com

  22. Terina says...

    I LURVE these outfits! Definitely do more posts like this! :)

  23. Love these outfits, and gosh the model is beautiful!

    I have to say I think you’d have to be really careful with the monochrome – could look like scrubs from first glance!! But the blush outfit she put together looks amaaazing.

  24. Shannon says...

    Love looks 3&4

  25. wb says...

    Like this a lot. But high-wasted jeans….WHY?

    • Jaclyn says...

      Because of the mom pouch!

    • Trish O says...

      i think high-wasted jeans make my mom pouch look so BIG…like it just sits right on top. Blagh. I like a nice cut across the pouch look. Jeans, so tricky to get the right ones for you.

    • Liz says...

      I find them more flattering. I also have a long torso so low rise jeans just don’t work for me.

  26. I thought this was super cute! Especially the last one! I never thought about wearing my off-the-shoulder top like that! Very creative!

  27. Claire says...

    Really cute. I think button ups look good with jewelry and scarves too. But right now all I want out of life is high waisted, loose fitting blue jeans.

  28. Lily says...

    I really enjoyed this post. Whenever I like an outfit in a magazine or on tv I never know how to get that x-factor in my own outfits. This helps with that! Can lisa be a regular columnist?

    And beauty uniforms for both women pretty please!

  29. I really appreciate this post and would love to see more like it! I own exactly one button-up that I never wear cause I can’t figure out how to wear it! I’m saving it for winter to layer under a sweater in the same camel hue (not a novel idea I know but one I saw on a week of outfits post and really liked. Might try some of these ideas too:)

  30. foundryandforge says...

    V important question (as I am petite) – How tall is Natasha? :)

    • Stella Blackmon says...

      She’s 5’00” :)

    • Abigail says...

      I wondered the same thing with that pink blouse in mind. COJ, we’re probably not alone…would LOVE to see more petite women featured in your style posts!!

  31. Tara says...

    I really appreciate the “why” behind the styling. I agree it looks so effortless & cool! It’d be nice to see more of this with each new season.

  32. Laura says...

    I have yet to find a button-up shirt that doesn’t gape at the chest due to my DDs- would love to know if anyone has a good brand for bigger-chested ladies

    • Ana says...

      Laura – I have the same problem and the solution is double-sided fashion tape. I put a strip of fashion tape in between the chest buttons of every button-up top I have and it works perfectly, keeps the buttons laying flat and no gaping ever! I buy a big package of the tape off amazon and it’s so sticky it lasts through a few washes.

    • Amanda W says...

      I only buy oversized button-ups for this same reason.

      My two favourites are from Zara (similar style:
      https://www.zara.com/ca/en/woman/tops/view-all/oversized-shirt-c733890p4908534.html) and Aritzia (http://www.aritzia.com/en/product/veritas-shirt/59164.html?dwvar_59164_color=1275). I was worried they would make my apple-shaped body look even more top heavy, but they really had the opposite effect and look more proportionate– and never any gaping! Hope this helps, I know the struggle :)

    • Wendy says...

      I like popover shirts. Has the collar but no buttons all the way down.

    • I have the problem too. When I was in a professional work environment and my buttons always were close to popping open, I would find a button-down that had a bit of stretch to it. Then I would take it to the tailor and have just the gap sewn shut and pull my button-down overhead.

    • Kate says...

      I find Uniqlo shirts fit really well and reliably – I’m a J cup!

    • Krista says...

      The only button down shirts I have found that don’t pop open are the ones from Duluth Trading. Although these are mainly flannel or work shirts.

    • Christine says...

      I have DDDs and always use fashion/double-sided/hollywood tape, even if there is no stretching gap – because I find that you can see my bra if i shift around in the shirt. My current favorite white button-up shirt is from LOFT of all places – I don’t see it on the site now, but it’s “pre-softened” or something like that and it’s super comfortable without the fit issues of other shirts. The Gap boyfriend shirts are another good option.

      I also love the popover option, which seems to have less fit issues for larger busts.

    • Roselyn says...

      GAP! Super soft and does not gape. Their boyfriend shirts, to be specific.

    • dona says...

      I have one word for you: Bravissimo. It is a British on-line bra and clothing store. It is only for large breasts and takes your shirt or dress size and then your boob size, so clothes actually fit, IT IS THE BEST. I am a 32HH.

  33. Angela says...

    I really appreciate this post, as it takes the cost factor out of the picture. You can style yourself at any price point using a post like this and I would to see more like it.

    • Elle says...

      That’s such a good point. I agree!

  34. The character Molly on HBO’s show Insecure wore a button-down with an off-the-shouldr sweater on the most recent episode. The ladies on that show have the BEST style…besides it being entertaining as hell I pretty much watch it to see what they’re wearing each week. It’s like Sex and the City 2017.

    • Joanna Goddard says...

      yes SUCH good style. i love when issa dresses up — her makeup is always so, so good.

    • Katie says...

      I’m obsessed with this show. The characters, the style, the humor, all of it. SO GOOD!

    • Mb says...

      OMG YES! I am a huge fan of that show’s stylist. Issa has awesome taste and Molly’s style is more professional and subtle but she also brings it when she is out of her workplace. I am obsessed with Issa’s wardrobe.

    • Lauren E. says...

      I second! I love love love the clothes on that show, from Molly’s workwear to Issa’s PJs.

  35. Sarah says...

    Lovely clothes, lovely women! Thank you for sharing these tips.

  36. KRA says...

    Would love to see a Beauty Uniform for Natasha Janardan!

    • Joanna Goddard says...

      great idea!! she actually has an identical twin, too.

    • Hannah N says...

      I’m friends with Natasha and Meghal! They actually have a youtube channel with makeup tutorials: https://www.youtube.com/channel/UCzXtkiRsRbGvzO73XL3UGhQ

      aaaand they’re gonna be so embarrassed I shared that, but what are friends for ;)

  37. These are great! And I love the explanations. I always see things similar to this, but for some reason, can never figure out what the details are that make it stand out to me in the first place. These feel unique, but attainable, and having the explanations makes it memorable for my word-oriented mine. :)

    • Joanna Goddard says...

      Same here! Lisa is actually the former director of styling for Madewell — so she really knows how to get that effortless, cool look :)