How to Style Oversized Sweaters – Winter Edition

As part of my #WinterStyleChallenge, I’m featuring a new look each week with different styles that feel so right during the chilly Winter weather. I do a new look every day on Instagram with a video with tips and tricks on how to style the outfits. Each post is linked to with suggestions for your favorite pieces. Click on the photos to check them out!

With the Winter Challenge, I am adding how to style outerwear to each outfit, too! Which jacket or coat works well, as well as scarves, hats and other fun accessories.

This week is a beloved staple of Winter style – the oversized sweater. I’m going to talk about the different styles of oversized sweaters and give you tips and tricks on what to wear with them – including jackets and coats. It is Winter after all, and we must work with the weather. 


Today’s style is a favorite of mine (I seem to start my challenges off with my favorite sweater brand – Wooden Ships Knits) This little number has a lot going on, which isn’t something I normally go for. I’m more simplistic when it comes to my wardrobe but somehow this one works.

This sweater is cropped AND distressed AND has print on it. I couldn’t resist it, though. VINYL. It speaks to me as a mid-40s rocker chick 👩‍🎤 and no one can tell me vinyl isn’t the best way to listen to music! The amount of distress on this sweater calls for some ripped up jeans – and my favorite classic Doc Martens 1460 boots. I added a fun oversized scarf to warm it up a bit AND this particular scarf happens to have a print of John Lennon on it.

In today’s video, I’ll talk about the best jacket to pair with this outfit and how to overcome the bulky nature of the sweater so that you are comfortable. 🧥

Check out my post today for suggestions on the pieces in this look! I added a few distressed black jeans – one just cut at the knees and another that’s a bit more ripped up. Unfortunately, Wooden Ships is not available through the app so I added a few suggestions for sweaters. You’ll find my docs on there and also my recommended jacket for this look.

Shop this Rocker Chick Look!


If you don’t know me (Well, you could probably tell just by my photos) I love some over-the-top styles – like exaggerated features. That’s why my hair is a color red not found in nature 🧑🏻‍🦰

So with an exaggerated feature in and of itself – oversize sweaters – I also adore when the neckline is over the top, too! Like this cowl neck sweater. Now, this one is really cool, because you can wear it two different ways, like this as a cowl neck or as an off-the-shoulder look, as well. But this being Winter, I am not too into exposing my shoulders to the cold air, so this is my favorite way to style it for right now.

I’ve worn this sweater a million different ways (over dresses, with skirts, with trousers…) but the oversized sweater with skinny jeans and boots just screams winter coziness and is a New England classic. I chose a dark wash skinny for contrast with the cream and my favorite mahogany Frye boots – the color is so rich and feels decadent. 💋

You can’t really wear this look with a tighter style jacket or coat. For this particular sweater, it’s too long for a short puffer coat and the cowl makes it hard to zip up a coat. Have you ever zipped up your jacket and got your shirt caught in it because there is so much fabric? That’s what we’re looking at here. So check out my video for tips on how to add a coat to this look for when you go out!

I’ve added suggestions to my post for today’s look. The jeans are Levi’s and so incredibly comfortable. The Sun and Moon earrings are from @boho.statement and are so light and comfortable!

Shop this Cowl Neck Look!


So this outfit is literally what I wear when I’m home for the day and doing work. It’s for when I’ve done my workout, I’m out of my PJs and want to feel human. And this sweater is my “house coat” 😂

What makes this sweater so amazingly comfy and easy to live in is that I decided to size up when I bought it. I normally wear a size small, but after trying it on, I knew I wanted to get a size or two bigger so it had that cocoon feel while giving me the room to do my busy work throughout the day. So I sized up to a L/XL so that I would get that dreamy flow and cascading collar. With a pair of black leggings, a seamless cami and some Ugg slippers, it’s a dream lounge look.

But don’t you hate it when you realize – shit, I have to get on a Zoom call later! Or – Damn it, I forgot I had that appointment! No need to tear off your hibernation wear, just add a few accessories to complete the look!

You can’t deny the Fosse style this look has going for it – the all black, form-fitting bodysuit look.👯‍♀️ So go bigger Fosse and grab am oversized brightly colored scarf and a pair of black booties to zhuzh it up! 💃And I’m loving this Fenty Beauty Gloss Bomb Cream in Fenty Glow as a natural lip color for everyday casual. I tried out their new Snap Palette in 7 Cadet and like that I could make it subtle with the more vivid pigments 🤎💛💚

The length of this kind of sweater makes it harder to wear shorter jackets and the bulk of the extra fabric in the arms can be uncomfortable in standard arms. So check out my video to see what coat I pair with this look for the best comfort and style.

I’ve linked the clothing and the makeup in my post so if you’re looking for a super easy but sexy way to spend your day at home, then get shopping!

Shop the Oversized Cardigan Look!

Day 4

Today I decided on a somewhat preppy look – but this is me, so I had to add some rocker chick to it 😂

This Wooden Ships crewneck is perfect for laying so many different tops underneath. I usually go for a stretchy cami and a scarf, but I love the look of a chambray button-down underneath it. Instead of going with some traditional trousers, I took it up a notch with these faux leather kick crop pants and some oxford heels. Add a long layered necklace, some silver bangles and cute sparkly studs ✨and you’ve got yourself a great day to night look.

Wooden Ships is one of my very favorite sweater brands and unfortunately they are not on the app (LTK – PLEASE get them on board! 🙏) But definitely check out their sweaters, they are amazing! I’ve linked to a few open knit oversized sweaters on my post today just for suggestions. The pants are on sale and I also suggested some chambray shirts, as well!

Shop this Preppy Look!


There are so many styles of sweater sleeves and I love the dolman sleeve for many reasons. It has a dreamy, boho quality to it and if you get a boat neck, it looks stunning off the shoulder. 🥰 It gives extra room if you are active throughout the day (re:picking up after your kids, or significant other 🙄 ) And, I know this sounds weird, but they give room in the armpit because let’s admit it, going in and out of warm rooms, it can get a little sweaty 😂 If you don’t like tight fitting arms, then a dolman sleeve is for you!

I love this sweater for every day use but it dresses up well with a pencil skirt and heels. I added a long pendant necklace as well as a fun faux fur infinity scarf! For me, I’d wear this scarf if I were out in an office all day or out for dinner. I love scarves both indoors and out. But if you get warm, you still have a necklace to dress up the look. And it makes it easier for outwear since it’s already a part of your outfit!

Again, dolman sleeves can be a little harder to wear with a coat because of the extra fabric under your arms. Check out my video to see what I coat I will wear with this outfit today! 

Shop this Work From Home Look!


I love this look from my #FallWardrobeChallenge – an oversized dolman sweater from Wooden Ships under a fun pair of boyfriend overalls. Because of the open knit and the light cotton, the sweater colors well under the lower cut overalls. And nothing better to finish the look than a pair of Converse Chucks high top sneakers ❤️

I’ve decided on my new theme for next week and it will be interesting because I never really dress specifically for this theme. So it’s going to be fun for me!

Follow along with me every week on Instagram (@thestyledefiner) for up-to-date styling tips and tricks!

And check out my on the app (you can grab it for your smartphone!) My handle is @thestyledefiner 

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