Whenever I buy a new piece (or before I even do), I like to run through how I’d style it. Sometimes that means mixing it with my existing wardrobe, sometimes it’s more of a dream-closet experiment. Half the fun is getting excited about the little things like getting dressed every day. The other half? Making sure the piece is actually realistic for my closet.
Enter: GAP’s button-up shirt (or organic cotton Big Shirt, according to GAP). I got it in a purple-leaning-burgundy, but it comes in a ton of colors. (If your size is sold out in burgundy, Gap Factory has a similar option here or I love this one from J.Crew.) At first glance, I loved this shirt. Second glance came with, “Okay, how would I really wear this, though?” Consider this post my third glance — 7 outfits I can truly see myself styling it with. Also in the mix: the fall trends I’ve been eyeing, the similar pieces already in my rotation, and some general inspo for fall (and honestly winter, too…sorry, it was an accident).
I decided to go with the tall sizing for this top, even though I’m 5’2-and-a-half on a good day. I’m leaning into the oversized, extra-long vibe, but these outfits would work with a shorter length (or even cropped) button-up, too. My personal plan is to mostly wear it buttoned and loose, but a full tuck, half tuck, or even left open with a tank under would work here. Let’s get into the seven fits.
Outfit 1: Pick Your Fall Shoe
There’s about four main shoe types that I plan on wearing this fall: pointed toe boots, low-profile sneakers, ballet flats (including sneaker-ballet-flats), and technical-ish sneakers (or dad sneakers). Pointed toe boots and ballet flats lean into the sleek nature of a button-up, sneakers make it feel less corporate. As for the rest, I’m loving on all gray outfits right now with a pop of burgundy, navy or dark cherry red.
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NOTES: Those jeans are the Levi’s baggy dad that we know and love, but in a perfect gray wash that works for any season. And, a moment for the adidas Toyko — I’ve been wearing them daily and love love love.
Outfit 2: Mixed Tailored Menswear With A Delicate Edge
Okay, for this one I wanted to take the button-up and combine two of my fave style moments: menswear-inspired pieces that lean tailored and utilitarian, with delicate add-ons like floral tights, strappy ballet flats, and little earrings. Adding a little edge with the black details is probably the most “me” part, haha.
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NOTES: I’ve been eyeing those floral tights for forever. They just add such a fun detail. And that barn jacket? SUCH a good denim wash. Ref has a similar one I’m peeking at, too.
Outfit 3: Refresh Your Lug-Sole Boots
I know we all remember when lug-sole boots were THE hot shoe for fall. Therefore, I know a lot of us still own them, and I always wanna find ways to refresh my existing pieces. Hear me out: yoga pants work. I swear. There’s something about the sleek leg that just lays perfectly over the chunky boot. And with an oversized button-up and leather jacket, it feels less casual. Wrong shirt theory? Maybe. Love the way the button-up peeks out from a cropped jacket, too.
NOTES: I’ve been eyeing all the cherry red bags, trying to narrow down which one I want. That one from Revolve is my most recent temptation, and it’s on sale. And yes, I already own lug-sole boots but how freaking cool are those with the yellow detail and wooden-clog-like heel?! GAH. Soooo tempted.
Outfit 4: Go Playful For Rainy Days
A little while back, Shana and I rounded up some rain jackets, and stumbled upon capes. Did I ever think I’d want a cape? No. Do I want a cape now? Yes. Cape, cropped or cuffed jeans, and cool boots: rainy day fit, ready. The button-up just adds a little something chic.
NOTES: Those boots are by the same brand that carries those cool lug-soles above, and I’m in love with the quirky-yet-wearable vibes. Also, I mean…how cute is that umbrella? Hahaha. It was def a mood booster for me, and only $17!
Outfit 5: Add A Little Edge
Since button-ups can lean preppy, and I don’t love preppy styles, this is my way of adding in some edge.
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NOTES: I’ve definitely been gravitating towards more romantic pieces than usual, and I feel like that leather bomber with red floral details is the perfect combo. A moment for the clogs + bag, too. So cool. And then, pointed-toe kitten heels because…always (the navy made me love even more). Last: those JEANS. It might be my favorite wash of jeans I’ve ever seen. It’s not quite blue, not quite black or gray. Deep inky-blue perfection.
Outfit 6: Combine Shades of Burgundy & Brown
I’ve been seeing brown + burgundy thrown together recently and love (shoutout to Shana for this, too). And burgundy pants feel waaay more wearable than I would’ve originally thought. But do I go for leather or denim?
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NOTES: I love that the utilitarian-esque bomber has a furry collar. The juxtaposition of it all, if you will. And a monochromatic moment? Forever a fan of that. Even if you went with a different colored button-up, the rest still works. Gray, brown, black or navy would be my other choices.
Outfit 7: A Moment For Fall Florals & Suede
I’ve been on a floral kick (which isn’t super typical of me). But the florals I love the most? The ones that lean more autumnal than springy. Mixing it with suede details just makes it even better. Softens the tailored look of the button-up, too.
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NOTES: How cool are those bags? The darker one is a find from Etsy, remade from…carpets (I believe). The second (lighter) one is a mini backpack with a floral moment that feels suuuper nostalgic to me. We may or may not have had a couch that looked slightly like that when I was little. Has a repurposed feel to it. Then: the GAP jeans. That little floral cuff is just such a fun touch to an otherwise simple denim silhouette. Last: that suede trench is everything to me right now, haha.
Cross your fingers this heat passes soon (please).
-Danielle
