How To Style An Oversized Shirt When You’re Petite

You may remember a couple of months back I took a weekend trip with Adam and Miles to Savannah, Georgia. We went so I could do a walk-through of the hotel for our 8th Annual #TBScon (details here!) and to have a little getaway with my boys. I packed adorable little sundresses to stroll through one of my favorite southern towns. But as a surprise to me, I was freezing! So I quickly popped into a Gap store and picked up this oversized shirt to keep warm. Best. Decision. Ever!
I knew that these big button-up shirts were popular, but I figured being a petite woman a shirt this large wouldn’t really work for my short frame. Alas, after trying it on in the fitting room with some warm leggings (the only pants that fit my growing baby belly!) I was sold. Talk about a super comfortable shirt that gives off super chic Ina Garten vibes. I am here for it!

How To Style An Oversized Shirt When You’re Petite

Once I got home I really wanted to experiment with the best way to style this shirt the proper way. Sure the leggings I purchased in Savannah were comfortable, but they’re definitely more for lounging at home, not so much wearing out and about. Not that I’m opposed to leggings outside of the house, but you know there’s a difference between home leggings and outside leggings, LOL!
And what I came up with is one of my favorite looks for spring – everything oversized! I know this may totally contradict my list of what not to wear when you’re short, but hear me out. When I wore this shirt with leggings, I for some reason felt off balance. Like a bobblehead. So after a little experimenting with items in my closet I came up with 3 tips on how to style an oversized shirt when you’re petite.

Pick The Right Button-Up Shirt

Right now, the oversized or big shirt is at just about everyone one of my favorite online retailers. It’s a shirt specifically designed to fit a little oversized on your frame. It’s different than just buying a button-up a size or two larger than your normal size. You want to find a shirt that still fits your shoulder/neck properly and is long, but not too long.


Length is also important, and this shirt from Gap hits me in the perfect middle spot right in my mid to upper thigh area. Certainly longer than a normal button-down, but not so long I’m drowning in fabric. That’s the thing, you want to be wearing the shirt, not the shirt wearing you. You can click on a few more oversized shirt options under $100 I’ve found recently too. I also own this one from Aerie which is so good!

Remember To Balance Out Your Look

Balance is essential with any look you create, whether you’re petite or not. But for us short girls it’s especially important. As I said, I didn’t love the look of this shirt with leggings, I just felt like it didn’t balance out my 4’11 frame properly. So I knew that I needed slimmer pants, but nothing too skinny.
That’s why I brought out my favorite Levi’s 501 Crop Jeans. (Note: I cut the bottom of these jeans myself because they were too long.) They’re straight, but not too skinny and worked well with the oversized top. Both of these pieces together totally remind me of this menswear look from the PLIG archives where I’m wearing the same jeans. Oversized shirts and looser jeans are best fashion friends I suppose.

Show Some Skin

I know what you’re thinking: Cathy how are you talking about showing skin at the same time as wearing oversized clothing?! Hear me out! If you pay closer attention, there is a lot of skin showing in this look. The top buttons of my shirt are undone, and I have my sleeves rolled up to the 3/4 length. In addition to that, I have holes in my denim, a crop cut to my jeans, and open-toe shoe. That’s a lot of skin!
When you’re wearing a lot of fabric like this, you want to be able to show a little skin off. This is where the balance of the look comes in. If I was wearing my full-length flare jeans and closed-toe shoes with this shirt with the cuff down, I’d be so covered and get lost in all the fabric. Subtle hints of skin make this look work and help you style an oversized shirt when you’re petite the right way.

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