Here's How to Wear An Oversized Sweater In Winter
I didn’t always dress casually. It’s been a slow slide into my current state, which is equal parts ‘mommy drinks’ and laid-back Angeleno. With ample experience toeing the line between understated and sloppy, I’ve finally landed on a winning formula and it centers around finding creative ways to wear oversized sweaters with polished pants. Yes, it’s mind-bogglingly simple, but it's also unbelievably versatile and— hark! — comfortable.
Hilariously, despite living in LA, I’m always cold. Our chilliest winter days rarely dip below 55 degrees, which is positively balmy compared to the brutal winters I survived in NYC for a decade. While I wore coats, heeled boots and a veritable smorgasbord of layers with abandon back then, I’ve since whittled down my uniform considerably, opting for as few pieces as possible. With that, a cozy, oversized knit is now a non-negotiable, particularly in the winter months. And while LA is the denim capital of the world, I’ve made a concerted effort to not reach a never-nude level of attachment to my jeans. Instead, I’ve eschewed denim for the grown up alternative; trousers. With those basic arguments aside, allow me to point out the crucial styling lessons I have learned during the course of this long and unwavering commitment to one formula.
There Is "Oversized" and Then There Is Just Plain Baggy
This is a precarious pitfall and you're particularly vulnerable when shopping online. Intentionally oversized silhouettes feature thoughtful details like sloped shoulder seams, curved hems, artful necklines and ribbed cuffs, all of which highlight the intentionality of the fit. Wearing a five-sizes-too-big sweater will result in the shoulder seams hitting at your elbows, the hem — loosely — swinging at mid-thigh, and sleeves that unravel uncontrollably. Not a good look. Make sure you're getting one from the former camp. Within the oversized silhouette category, you can opt for a range of styles to highlight your body type. Personally, I’m partial to turtlenecks because, well, warmth, but other great options include crewneck or v-neck silhouettes. Here are a few of my favorite recent purchases.
Oversized Cashmere Turtleneck
Brushed Oversized Crew
The Elder Statesman
Balance Your Silhouette
To avoid looking like you’re fighting a losing battle with a black hole of fabric, you’ll need to balance the oversized style with your pants. A skinny, stovepipe trouser that crops at the ankle is ideal for pairing with slides, loafers or tucking into flat boots — as does a kick-flare style. (It will also pair well with a pointed pump and a clutch for evening.) To create a less top-heavy silhouette, team the knit with a flared or bootcut trouser and a heel.
Houndstooth Tweed Pants
Thilde Ankle Slit Cropped Pant
Straight Leg Velvet Cotton Pants
Calvin Klein 205W39NYC
The real benefit of this formula, in my opinion, is that it is the sartorial equivalent to bowling with bumpers. The countless hours of my life I’ve wasted Rubik's cubing the contents of my closet have now been replaced with playing within this simple framework. Rather than “What am I going to wear?!”, I find myself asking “Should I mix textures, or colors, or prints?” I think we can agree that's a more fun question to answer. I’ve recently mixed a fisherman knit with tweed trousers, a chunky cashmere turtleneck with a brocade pant, and a red hoodie with camel khakis. The opportunities are plentiful, so go ahead, knock yourself out.
Vintage Soft Pullover Hoodie
Cropped Floral Brocade Trousers