If my Instagram is anything to go off of, you’ll notice that I’m a big fan of outfits that are just as comfortable as they are stylish. That’s why you’ll often catch me rocking a roomy, breathable shirt, like an oversized button-up. They’re a timeless staple, ridiculously comfortable, and incredibly versatile, giving you a bunch of fabulous outfit options. But if you’re new to the oversized look, they can be tricky to style. So, today, I thought I’d share a guide on how to style an oversized button-up to look chic every time.
How To Style Oversized Button-Up
With Relaxed-Fit Shorts & Sandals
First up, here’s an easy, breezy way to pull off the oversized shirt look. Start with a lightweight button-up, like this Oxford shirt from H&M in either blue or blue stripe. Then, pair it with relaxed-fit shorts. The key is choosing shorts that fit loose, but don’t look baggy. Finally, add a pair of leather sandals, like the Bay slides from Sam Edelman.
With Straight-Leg Jeans
An oversized white button-up shirt puts a modern twist on this classic look. Grab your favorite oversized button-up, then pair it with another must-have, high-waisted straight-leg jeans. Levi’s never lets me down. And, as for the shoes, white sneakers are an easy choice for me.
With A Skort & Slingback Pumps
I recently donned this look as one of my new favorite minimalist classic outfits, with a tailored trucker jacket worn over my shoulders. Those of you who need a colder weather look will appreciate how warm it is when styled as a regular button-up shirt, even if you choose to leave it unbuttoned with a plain tank underneath. I paired it with this sleek black skort from DISSH and black slingback pumps to add in some feminine details.
With Wide-Leg Trousers
Another super chic way to wear an oversized button-up is to pair it with some wide-leg trousers. This updated office-ready look is also great for any occasion that calls for business casual attire, or really whenever you feel like dressing up a bit. The Effortless Pant from Aritzia definitely lives up to its name! Add a black leather belt to break up the look, then grab whatever shoes flats or heels you’re feeling for the occasion.
With Matching Shorts
While a matching button-up and pants set can easily give more of a pajama vibe, swapping the pants for shorts instantly transforms the combo into a chic, vacation-ready look. This button-up tunic and matching shorts are perfect for styling over a swimsuit, too! Add these Sam Edelman sandals in ‘almond patent’ to complete the summer cazh look.
With A Tank & Black Slip Skirt
For this next look, start with a basic white tank, add a black slip skirt, and then throw on your button-up (the color is entirely up to you). Black leather sandals are the perfect shoe for this outfit, keeping it casual yet polished.
And, if it’s a bit chilly out, this is exactly the kind of outfit I would wear with a denim jacket. Be sure to read my post on how to style denim jackets for more outfit ideas!
Or A Knit Sweater Maxi Skirt
Or, for an outfit that can really hold up against cold weather, wear your oversized button-up with a thicker maxi skirt, like this knit sweater maxi skirt from Topshop. I’d pair it with chunky, lug-sole boots to really combat the cold.
With Black Faux-Leather Pants
How about an edgy, youthful look? For an outfit that will even impress your teenage daughter, pair your oversized button-up with faux leather pants. Style your shirt with a half-tuck, following the instructions I included below.
Over A Fitted Midi Dress
For those of you who feel your best in a dress, you can pull off the oversized button-up look, too! Just grab your favorite fitted midi dress, slip on your button-up, and either wear it open and relaxed, or tie it at your waist to accentuate your midline.
With Wide-Leg Jeans & A Blazer
Another one of my favorite pairs of jeans, the Ava Ultra High-Rise Wide-Leg Jeans from H&M, is a good starting point for our final outfit. This time, you’re going to tuck in your button-up and add a blazer for an elevated, yet still casual look.
How To Tuck Oversized Button-Up Shirt
A full tuck is great for a classic-fit button-up shirt, but these days, I’m seeing chic women in oversized button-ups rocking the half-tuck. Here’s how to master this trendy look.
Step 1: Button the shirt to your waistband.
Start by buttoning your shirt all the way to the waistband of your bottoms, or a little higher, depending on your preference.
Step 2: Tuck the left panel into your pants, skirt, or shorts.
Carefully tuck the left panel of your shirt (the side with the buttons) into your waistband, leaving the right panel (no buttons) untucked.
Step 3: Smooth excess fabric.
For a smooth, neat tuck, tuck the shirt flatly into your waistband, rather than bunching or stuffing. Then, carefully cuff the hem of the shirt beginning at your hip to create an angle going from the tucked to the untucked side.
An oversized button-up shirt is a wardrobe essential for every stylish woman.
A good-quality, oversized button-up shirt is one of my most worn wardrobe essentials, mainly because of the sheer number of outfits you can create with it.
While the outfits I shared in this post are a great starting point, I would love to know how you’d style this fashion essential. Share in the comments below, then head over to the blog for more of my favorite things!
