The oversized sweatshirt trend is skyrocketing for 2021, and honestly, we couldn’t be more thrilled. The problem is, plenty of fashionistas are scratching their heads. Do we just wear out boyfriend’s sweatshirts and be done with it? No, hon. Although it’s oversized, it still needs to be styled right.

If you’re struggling with your oversized style, we’re here to help. Below you will find some of the most trendy styling tips for oversized sweatshirts. We’re even sharing a few of our top picks so you can join in on the trend, too.


Thigh-High Boots

To be honest, your oversized sweatshirt doesn’t necessarily need bottoms. If it’s long enough to be worn as a dress, more power to go. What you need to consider is what shoes you’re going to wear, though.


While I’m a big fan of wearing combat boots or bright white sneakers with an oversized sweatshirt, the crowd favorite remains to be thigh-high boots. The pairing is pure perfection. The oversized, comfortable look on top and the polished and refined style down below. It’s a match made in heaven, babes.


Mom Jeans


To be honest, any pair of denim will work. But since we’re on the subject of fashion dos and don’ts, I will recommend wearing your favorite pair of mom jeans with your coveted oversized sweatshirt.

With a mom jean and oversized sweatshirt combo, you’re rocking the ultimate casual and comfort style. The pair looks completely effortlessly. When wearing an artsy oversized sweatshirt with designs and patterns, the look gets a chic makeover.

That said, it’s easy to make this style yours.



Listen up – the goal of an oversized sweatshirt isn’t to be so big that you can’t put anything over it. That’s because you still want to have enough room to layer and be able to show off your silhouette, even if it’s only slightly.

oversized sweatshirt sexy leather jacket


When layering, the look is entirely up to you. Women that want to take it to the edgy dimension will have no trouble pairing it with a sexy leather jacket. On the other hand, the sporty babes might like to throw on a bomber jacket over their oversized hoodie. Both looks can’t miss.


If you want to combine summer styles with winter picks, consider layering with your go-to slip dress. Yes, slip dresses are 100% on-trend and capable of being worn over your oversized sweatshirt. By doing so, you give your summer wear a cozy makeover that can be worn all through the chillier months. Multi-seasonal outfit? Yes, please!




I know what you’re thinking – leggings again? What can we say? Leggings are the go-to for comfortable fashion, and they go well with basically everything in our wardrobe. When you’re looking for a cozy and relaxed everyday look, it’s leggings to the rescue.

The fun thing about leggings is you can totally mix and match. Some ladies might want to keep it cute and flirty with neutral tones like pale pink or lavender. Others might want to pair their leopard leggings with a geometric-patterned oversized hoodie. Basically, anything goes when it comes to a legging and oversized sweatshirt pairing!


Plaid Pants


It’s no secret that the vintage look is entirely on-season. So why not indulge in this delightful look while wearing you’re oversized sweatshirt, too? If you have a favorite pair of plaid pants, it’s time to bust them out for fall and winter fashion combos.


Don’t hesitate to create a knockout color combo, either. While some ladies prefer the black or brown toned-down plaids, others want all eyes on them. Looking to turn heads and add a pop of color to your winter wardrobe? Consider bright red plaids that stun.



Skirts and hoodies? While this may have been a fashion faux pas years ago, it just happens to be one of the number one looks for 2021. There are so many ways to bring this hot look to life.


First, consider a mid-length skirt. A mid-length option will make sure that your legs stay nice and warm, even when the temperatures drop. We love this option because it has that popular vintage charm and button-down look that everyone’s craving.


A bodycon skirt is another popular pick. With this option, you can show off a little more of your curvy figure compared to a mid-length skirt.

skirt to wear with oversized sweatshirt

For a professional twist, consider pencil skirts. Not only is this a charming and elegant way to wear your oversized sweatshirt, but it’s another choice that enhances the female form. If you’re looking for a way to show a little leg and a little body-ody-ody, pencil skirts may be the way to go.


Lastly, consider bedazzling down below with a sequin skirt. The flashy sequin design will play well with the rather casual look up top, creating a more iconic combination than peanut butter and jelly.


Top Oversized Sweatshirt Picks

Okay, we can be honest and say we love them all. But if you’re struggling to decide which ‘fit is right for you, keep reading. We are showcasing our top three oversized hoodie picks. Remember that you can easily dress them up or down depending on your accessories, bottoms, and footwear.

GAP Oversized Hoodie


This hoodie is the go-to pick for many women because it comes in a delightful pale beige-pink shade that pairs well with anything. Whether you’re planning on rocking thigh-high delights or want to layer with your favorite slip-on dress, this oversized hoodie does it with ease.

Urban Outfitters Project Social T Oversized Sweatshirt


Are you looking to make a statement with your oversized graphic sweatshirt? We love this one because it has a vintage touch with a lovely message that anyone will enjoy. This is the go-to option if you’re planning to wear leggings, mom jeans, or skirts and look amazing doing it.

ASOS Tie-Dye Oversized Sweatshirt


We can all agree that the tie-dye style isn’t going anywhere. We can also all agree that we’re not complaining. If you jumped aboard the tie-dye trend this year, you don’t have to hop off just yet. This adorable tie-dye oversized sweatshirt proves that the tie-dye look is going to soar into the chillier months, too.

Banana Republic Oversized Sweatshirt


Not everyone is into hoodies. If you want to dive into the oversized sweatshirt trend but don’t want to struggle with a hood, don’t panic. There are plenty of oversized sweatshirts on the market that don’t have hoods, such as this adorable Banana Republic Oversized Sweatshirt. It’s a cozy blank slate that allows for endless styling abilities.

Waffle Knit Oversized Sweatshirt


Okay, so this one is more of a sweater than a sweatshirt, but we had to add it in! Knit is a style must. If you’re into knit, then you’re going to love the waffle-knit pattern of this snug oversized sweater. It’s available in several color combinations, including a very fashionable blue and lavender color block blend.


Final Words

Oversized sweatshirts are one of the biggest fashion trends for 2021. We love it because it’s comfy and casual, yet pairs well with just about anything. Whether you’re a legging-loving lady or want to show off some leg with a mid-length skirt, you can rock your oversized sweatshirt with pure confidence this season.

What’s your favorite way to wear an oversized sweatshirt?