How to Wear Oversized Blazers Without Looking Boxy or Sloppy

IG: parvina.kanbar

Hi guys, so grab an iced coffee or a matcha or whatever you are feeling right now, cause we really need to talk about something super important today. We are diving deep into the oversized blazer trend.

But then you try it yourself at home, right? You order one online, it arrives, you put it on, and suddenly you look like a literal rectangle. Or worse, like a little kid who raided their dad’s 1994 office closet. It is the most frustrating feeling in the world.

I literally remember this one time a couple of years ago when the trend was just starting to blow up. I was so obsessed with the vibe. I went and bought this massive vintage men’s blazer from a thrift store. Like, way too big. I thought I was gonna look so effortlessly cool and chic for this coffee date I had on a Tuesday afternoon. Tell me why I showed up looking like a literal linebacker. I sat down at the table, and the shoulder pads were practically touching my ears every time I shrugged or moved. The guy kept staring at me with this very confused, polite smile. I realized halfway through my latte that I just looked like I was hiding a backpack underneath my jacket. Honestly I wanted the ground to swallow me whole right then and there.

But after a lot of trial and error – and trust me, there were errors – I finally cracked the code.

Rule #1: It is Literally All About Proportions

Okay so here is the thing. The number one reason an oversized piece makes you look boxy is because you aren’t balancing the volume. If you are wearing something huge on top, you kinda have to slim it down on the bottom. It’s just basic outfit math.

Think about it. If you wear baggy jeans with a baggy t-shirt and a baggy blazer, you are completely losing your body shape. Which is fine if you are going for that specific ultra-streetwear look, but for everyday chic? It’s too much fabric swallowing you up.

What you want to do is pair that big jacket with something fitted. A mini skirt is my absolute favorite way to do this. Showing some bare leg instantly breaks up the heavy fabric. Or if it’s colder out, go for straight leg jeans or even some really nice tailored leggings. Bike shorts also work so well in the summer for that Hailey Bieber kind of vibe.

You want the eye to see that yes, the jacket is huge, but there is a normal sized human underneath it! By keeping the bottom half of your outfit relatively sleek, you are telling the world “I wore this big jacket on purpose, it didn’t just happen to me by accident.”

Rule #2: The Sleeve Scrunch is Non-Negotiable

If you take nothing else away from me today, please let it be this. You have to do something with the sleeves.

When sleeves are too long and they cover your hands, it instantly drags the whole outfit down. It makes the blazer look like a mistake. Our wrists and forearms are the narrowest part of our arms. Exposing them makes you look so much slimmer and more put-together.

Me and my girls were at brunch last summer, and I had this gorgeous beige blazer on. It was intentionally oversized, really drapey and beautiful. But I didn’t roll the sleeves up before we left the apartment. I reached across the table to grab a piece of avocado toast from the shared plate, and my giant sleeve just dragged right through my friend’s matcha latte. It was a total disaster. Green milk everywhere, all over my nice jacket. That was the exact moment I learned my lesson.

Now, I use the hair tie trick every single time. Have you tried this? You basically just put a clear elastic hair tie over the sleeve of the blazer, right around your forearm. Then you pull the fabric up to scrunch it, and the hair tie keeps it magically in place all day without sliding down. It gives that perfect “I just casually pushed my sleeves up” look. It changes the entire silhouette of the jacket.

Rule #3: Define Your Waist (Even if it’s Secretly)

So you might be thinking, “Anne, how do I show my waist if I’m wearing a tent?” Fair question.

You don’t always have to belt the actual blazer itself on the outside. Honestly, I think belting blazers is a little bit 2018 anyway. What you want to do is define your waist *underneath* the blazer.

Leave the jacket completely unbuttoned and open. Underneath, wear a crop top, a fitted bodysuit, or just tuck your t-shirt tight into high-waisted jeans. If you wear high-waisted pants and a top that hits right at the waistband, you are creating a clear waistline.

When you walk, the blazer moves and opens up, and people can see your actual shape underneath. The contrast between the big structured shoulders of the jacket and your cinched-in waist underneath is exactly what makes this outfit formula work so well.

If you wear a long, baggy t-shirt untucked under an oversized blazer, you are basically creating a double box. We are trying to avoid the double box at all costs!

Rule #4: Pay Attention to the Shoulders and the Fabric

Not all oversized blazers are created equal. This is something people don’t talk about enough when they give styling advice.

An oversized fit shouldn’t mean “I bought a size XXXL that doesn’t fit my body structure.” A truly good oversized blazer should still fit your shoulders relatively well. The seam where the sleeve starts should ideally sit just slightly off your natural shoulder, not all the way down your bicep. If the shoulder drops too low, it pulls the armpits down, and you literally won’t be able to lift your arms. You will be walking around like a T-Rex all day.

I was digging through the racks at Goodwill last month with my roommate, trying to find some cool fall pieces. I found this incredible gray wool blend jacket. But it had these massive, intense 80s shoulder pads in it. I put it on and almost put it right back on the rack cause it felt way too stiff and boxy. I looked like a Wall Street banker. But then I realized, wait, I can just take the pads out. I literally took tiny scissors from my purse and snipped them out right there in the fitting room – sorry Goodwill! – and once those pads were gone, the fabric draped perfectly over my shoulders. It was a total game changer.

Fabric is huge. If you go for a stiff, heavy wool, it’s going to hold its boxy shape no matter what you do. If you choose a lighter crepe, a linen blend, or a softer cotton, it’s going to drape and flow with your body. If you are a beginner with this trend, always go for softer, drapier fabrics first. They are so much more forgiving.

Rule #5: Show a Little Skin

This sounds weird when we are talking about wearing a heavy jacket, but it really helps! When you wear an oversized blazer, you are covering up a lot of real estate on your body.

To counteract that heavy feeling, just show a little bit of skin somewhere else. It breathes life into the outfit. It doesn’t have to be a lot. A slightly lower neckline on your t-shirt or camisole. A crop top that shows an inch of stomach. Wearing a skirt so your legs are bare. Even just tying your hair back so your neck and collarbones are exposed.

If you wear a turtleneck, long heavy trousers, boots, and a giant blazer, you are completely drowning in fabric. There is no visual break. Skin acts as a visual break that tells the eye, “Hey, this is a fun fashionable outfit, not a winter survival suit.”

Rule #6: Don’t Forget the Shoes

Your shoes can entirely make or break the oversized blazer look. They anchor the whole thing.

If you are wearing a big heavy blazer on top and really tiny, delicate, flat sandals on the bottom, you might look a bit top-heavy. Like an ice cream cone. You want a shoe that has a little bit of weight to it to balance out the top.

I am currently wearing mine with chunky sneakers constantly. It gives it that perfect cool-girl street style look. A chunky loafer with some cute ankle socks is also amazing for fall.