6 Oversized Sweatshirt Amazing Styling Tips and Top Picks

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Oversized sweatshirts have become a cozy wardrobe staple, and honestly, we couldn’t be more thrilled. The problem is that plenty of fashionistas are scratching their heads. Do we just wear our boyfriend’s sweatshirts and be done with it? No, hon. Although it’s oversized, it still needs to be styled right.

Key Takeaways

An oversized sweatshirt still needs styling: balance the volume with fitted or polished pieces.
Thigh-high boots, mom jeans, leggings and trousers are easy bottoms to pair it with.
Layer a leather or bomber jacket over it, or a slip dress over it for a cross-season look.
Skirts, from denim midis to leather minis, give a sweatshirt a dressier twist.

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.

Table Of Contents

Key Takeaways
Thigh-High Boots
Mom Jeans
Layered
Leggings
Trouser Pants
Skirts
Top Oversized Sweatshirt Picks
Final Words

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 you. 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, a crowd favorite is 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 mom jeans and an oversized sweatshirt combo, you’re rocking the ultimate casual and comfortable style. The pair looks completely effortless. 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.

Layered

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.

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

If you want to combine summer styles with winter picks, consider layering with your go-to slip dress. Yes, slip dresses can be 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!

Leggings

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 mix and match. Some might want to keep it cute and flirty with soft tones like pale pink or lavender. Others might want to pair their leopard leggings with a geometric-patterned oversized hoodie. Anything goes when it comes to a legging and oversized sweatshirt pairing!

Trouser Pants

Vintage-inspired looks are always in season. So why not indulge in this delightful look while wearing your 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 green, blue, red, and purple trousers.

Skirts

Skirts and hoodies? While this may have been a fashion faux pas years ago, it’s now a go-to casual look. There are so many ways to bring this hot look to life.

First, consider a denim 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 trendy look that everyone’s craving. For a professional twist, consider satin maxi skirts. Not only is this a charming and elegant way to wear your women’s oversized sweatshirt, but it is so comfortable, and can be cozy if used with some legging warmers and a pair of boots!

A short leather 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. 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 midi pencil skirt. This is another choice that enhances the female form, and can make a casual look stand out!

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 five of our favorite oversized sweatshirt picks. Remember that you can easily dress them up or down depending on your accessories, bottoms, and footwear.

GAP Oversized Crewneck

We like this crewneck for its classic, easy-to-style look. Whether you’re planning on rocking thigh-high delights or want to layer with your favorite slip-on dress, this oversized crewneck does it with ease.

Urban Outfitters 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. Nothing can beat an oversized black sweatshirt.

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 women’s 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.

Oversized Crewneck Sweatshirt

If you’re looking for the classic oversized crewneck sweatshirt then we’ve got you covered. These sweatshirts are hoodie-less which can add versatility to whatever style you’re feeling on any given day. Check the link above for current colors and sizes.

ASOS DESIGN 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 knitting, then you’re going to love the waffle-knit pattern of this snug oversized sweater. Check the link for the current color options.

Final Words

Oversized sweatshirts are one of the most versatile pieces you can own. 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 women’s oversized sweatshirt with pure confidence this season.

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

Is it OK to wear an oversized sweatshirt?

Absolutely. An oversized sweatshirt is ideal when you’re feeling casual or running a quick errand, and with the right bottoms and shoes it can look polished too.

What size sweatshirt should I get to be oversized?

If the sweatshirt is advertised as fitting or as running small and the wearer is in between sizes, going two sizes bigger may be best for an oversized look.

Are oversized sweatshirts still in style?

The wonderful thing about oversized sweaters is that they are fashionable all year long! Relaxed, oversized fits have stayed popular for years, and an oversized sweatshirt or knit is an easy wardrobe staple in cooler months.

Kourtney Anderson

Makeup, Skincare & Hair Care Writer at Successible Life
Freelance Beauty Writer at Successible Life | + posts

Kourtney Anderson is a freelance writer for Successible Life and one of its most prolific contributors, covering makeup looks and techniques, skincare routines and ingredients, hair care and beauty shopping guides.