I was shopping with my mom recently and encouraged her to try on a sweater. It was more cropped, but oversized, something that she wouldn’t normally grab for. She was reluctant at first, worried that the cropped cut wouldn’t flatter her frame, and most of all, concerned that the oversized nature of the sweater was going to make her look bulky.
I encouraged her to try it on, and as I say with many of my clients you just need to give a go, there is no harm in just trying something one. Styling oversized clothes is something that doesn’t come naturally to many people. They’re afraid that they’ll make her look frumpy or for someone like my mom who’s petite in every way, it’ll make her look like she’s drowning in her clothes.
While this fear is valid, this simply isn’t true. At least it doesn’t have to be. I’m glad that we’re out of the early aughts of dressing (clearly not a favorite time period for me), and a lot of us are comfortable with the idea that everything doesn’t have to be tight. For the record, I’m not anti-tight. I don’t believe that everything should be oversized or extremely baggy, but I do believe in proportions and balance. The key to styling oversized clothes is understanding the balance you’re trying to achieve. You just need to know where you’re going.
My experience getting into oversized clothes
When I first started wearing oversized clothes in public (we’re not counting the years borrowing my dad’s t-shirts, those were fabulous but kept at home), that is mixing and matching oversized pieces in my looks, I began with an oversized sweatshirt. I’m pretty sure it was an ex-boyfriends, grey, a bit tattered. But absolutely comfortable.
The sleeves were too long so I rolled them a bit and scrunched them up my arms. Fairly certain I was wearing leggings and Uggs because, well, that’s what we did then, and I was on my way to fail Chemistry 105 for the third time. Iconic. The way I felt wearing the oversized sweatshirt was cool. I smelled a bit like cologne which felt a bit masculine instead of the predictable feminine sorority girl, and my sweatshirt was fitting three to four sizes too big, versus the true to size and tight, bright fitting sweatshirts that the girls around me wore. I stood out and I loved it.
Fairly certain I was wearing leggings and Uggs because, well, that’s what we did then, and I was on my way to fail Chemistry 105 for the third time. Iconic.
Wearing something oversized gave me a confidence that I couldn’t find in wearing something that was tight and showed off my body. It concealed my curves, but that somehow made it more interesting. It wasn’t about showing off my body, but showing off the vibe that I felt. I was empowered, and cool.
The benefits of styling oversized clothes
One of the things I love so much about wearing oversized clothes is the number of options it gives you. Take an oversized blazer for example. There are enough possiblities to wear the same blazer each day of the week and still be wearing a completely different outfit. You can wear her with a t-shirt underneath, you can throw a button up over that t-shirt and wear it unbuttoned as a layer, or button it half way exposing the shirt. You could wear it over a sweater, a turtleneck, a small jacket, a hoodie, or a dress. You could wear it on its own with nothing underneath. Because it’s oversized it gives you the versatility to wear it over and with so many things. How fabulous is that?
Having something oversized also means it can transition across seasons with you. In the cooler months you’re able to layer it up, and in the warmer months you can strip it down to simple pieces and keep the air flow going if you know what I mean.
The formula for styling oversized clothes
Styling oversized clothes is as simple as keeping in mind these few tricks. (Number three is my favorite.)
- Choose One Oversized Piece: Start with one oversized item (either top or bottom).
- Balance with Fitted Items: Pair with a fitted piece (e.g., oversized top with fitted bottoms).
- Add Structure with Accessories: Use a belt, or choose structured footwear to add definition.
- Layer Thoughtfully: Add layers to enhance the look without overwhelming your frame.
Ways to Style Oversized Clothes
These are some of my favorite ways to style oversized clothes. Just start with whichever one speaks to you and try it out. You literally can’t fail with fashion.
- Balance with Fitted Pieces
- Pair oversized tops with fitted bottoms like skinny jeans, leggings, or pencil skirts.
- Wear oversized pants with a more tailored or fitted top.
- Layering
- Layer an oversized jacket or coat over a slim-fitting outfit to add dimension.
- Combine oversized sweaters with long shirts or turtlenecks underneath.
- Belt It
- Add a belt to an oversized dress, shirt, or coat to create a defined waistline and add structure.
- Tuck It In
- Tuck an oversized shirt partially or fully into high-waisted pants or skirts for a chic, put-together look.
- Roll the Sleeves
- Roll up the sleeves of oversized shirts, blazers, or coats to add a casual touch and showcase your wrists or accessories.
- Play with Proportions
- Wear an oversized top with short bottoms like shorts or a mini skirt for a playful proportion contrast.
- Experiment with cropped oversized tops paired with high-waisted bottoms.
- Accessorize Boldly
- Use statement accessories like large sunglasses or chunky necklaces to complement the oversized silhouette.
- Footwear Matters
- Choose shoes that balance the oversized look, such as chunky sneakers, combat boots, or sleek ankle boots.
- Heels can elevate an oversized outfit, making it look more polished.
- Monochromatic Look
- Create a monochrome outfit with oversized pieces for a streamlined and sophisticated look.
- Cuff the Pants
- Cuff the hems of oversized pants or jeans to avoid dragging and to showcase your footwear.
My favorite oversized combos
You know me, I always like to provide options. So if you’re not into formulas or ways to style oversized clothes then this list can be a quick reference point for you.
Oversized Blazer + Slim-Leg Jeans + Heels: A chic, polished look that balances structure and fit.
Oversized Sweater + Leather Leggings + Ankle Boots: Cozy meets edgy for a stylish, balanced outfit.
Oversized T-Shirt + Bike Shorts + Chunky Sneakers: A trendy, casual street-style combo.
Oversized Denim Jacket + Midi Dress + Sneakers: A relaxed, feminine look with a touch of street style.
Oversized Hoodie + Leggings + Combat Boots: Comfortable and cool with a tough, edgy twist.
Get the look
Ready to test out oversized dressing? I got you:) Below are some of my favorite pieces when it comes to oversized dressing. If you notice, The Frankie Shop is really my favorite place for oversized shopping. Check out my links below for some of my favorite items from them!
