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I Refuse To Give Up On Wearing Hoodies — Here's How I'm Styling Them For The Office

Elevated? Check. Comfy? also check.

How to style hoodies for winter- Hoodie with an oversized coat

Usually when someone tells me that I look “comfortable” I know that it’s code for “you look like you put zero effort into your outfit.” But I’m of the school of thought that a low-effort outfit doesn’t have to be a bad thing. In fact, I think outfits look all the more stylish when they don’t require constant adjusting to fit right. That’s why nailing how to style hoodies this winter has been at the top of my to-do list, especially as I adjust back to working from the office.

This past year has seen a surge in comfortable dressing — anyone who was online shopping for clothes in 2020 was most definitely buying a lounge set of some sort. Much like everyone else, with nowhere to be but inside, my collection of sweatshirts grew exponentially, but when the outside world began to open up again, my priorities changed. Furry slippers were replaced by low strappy heels, oversized T-shirts took a backseat to tight cropped going out tops, and my beloved hoodies found themselves in the back of my closet while lighter fabrics came out to play for the summer.

But as soon as the temperature dropped below 70 (for about two days in September before jumping back up) I eagerly reached for my cozy sweatshirts only to remember that unlike eight months ago, I actually have places to be now. With the return to working in an office and sporadic social events, my go-to cozy combo of an oversized hoodie and matching sweatpants wouldn’t cut it anymore. So it became my mission to find chic yet uncomplicated ways to wear my hoodies for days when I needed to look my best.

The “elevated hoodie” is definitely not a new concept, at least not to fashion’s insider crowd. Street style images from 2018 and 2019 were filled with influencers and editors in Paris or New York paring casual hoodies with statement coats, sleek blazers, knee-high boots, and skirts of all lengths — the result? A sophisticated yet laid-back vibe that screams “I’m cooler than you, and I didn’t even try.”

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There are days though when putting on a blazer negates the comfort of wearing a hoodie — sometimes it feels like too much fabric which can be restricting, and not to mention hot. On those occasions, a full-on matching sweatsuit is required. Any fashion-inclined person can attest to the fact that a matching set is the easiest way to look put together, and this holds even more true when it comes to loungewear. While throwing on a hoodie and sweats may look too lax for the office, a matching hoodie and sweatpants in a neutral color and luxe fabric like cashmere makes me feel luxurious — add a soft oversized coat and you’re practically ready to walk down the runway and be back in bed in the same outfit.

With the addition of new trendy hoodies to my collection, I’m more pumped than ever to be the most comfortable dressed person at the office. Here are five ways I’m styling my hoodies this winter for a comfy yet elevated look.

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With A Blazer

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Pairing a structured oversized blazer with a loose-fitting (but not oversized) hoodie is a very literal interpretation of business casual. As seen above on the streets of Milan this past Fashion Month, opting for a neutral colored blazer in the same color palette as your hoodie and sweats makes it looks like you tried just enough while still having that effortlessly chic effect.


Minimalists have long known the secret for elegant dressing: less is more, especially when it comes to color. Something about wearing one singular color or various shades of the same color evokes a feeling of luxury when done right. Pairing a neutral-toned hoodie with matching sweats or leggings, and topping it off with a coat in the same color gives off major “that girl” energy.

Wrapped Up In A Long Coat

Never underestimate the power of a long oversized coat to take even the most basic outfit and turn it into a chic street style moment. Choosing a coat in a dark color with structured tailoring is the way to go when styling this look — the sleek shape of the outer layer offsets the size so as to not look too slouchy, as some oversized pieces can tend to look.

With A Trench

Trench coats are a staple in every fashionable person’s closet so it’s no wonder that throwing one on over a sweatsuit takes it from slouchy to chic in a matter of seconds. Add in a pair of dad sneakers and you’ve got a celeb-approved, influencer-loved, and Instagram-worthy fit.

With A Midi Skirt

I’ve long been a fan of streetwear brand Fear Of God’s “Essentials”, but discovering their knit hoodie in this warm green color ignited a deeper love for hoodies than I thought possible. The perfect blend of a knit sweater and a hoodie, this oversized piece is apt for dressing up — the best way to elevate this piece? Pair it with leather bottoms. A midi skirt is an unexpected pairing with a hoodie but it just works — a subtle grunge vibe if you will.