3 Stylish Ways to Wear Your Hoodies and Pullovers

These pullover and hoodie outfits will bring your cozy favorites beyond basic.

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Gray hoodie

Hoodies and pullovers are foolproof garments when it comes to warmth and comfort. However, sometimes it’s all too easy to look like you’re wearing sweats or gym clothes when you’re rocking a hoodie.

Fortunately, there are lots of stylish ways to make hoodies and sweatshirts work as part of a fashionable wardrobe – you just have to get a little creative.

Below, I’ve created some pullover and hoodie outfits to get your inspiration going! Scroll down to see them.

Look 1: Athletic Chic Hoodie Outfit

Outfit set with black hoodies, black pants, and sneakers and a fanny pack.

Products: Hoodie – Macy’s, Pants – ASOS, Shoes – ASOS, Fanny Pack – Urban Outfitters

Any basic oversized hoodie is a great piece to own if you want to be comfortable. They are super trendy and can look good with anything.

These pleather pants are fashion girl-approved, and a great unexpected pairing for an oversized hoodie. Meanwhile, adding sneakers and a pop of green with a lime fanny pack gives the outfit street style appeal.

Tips for Styling Basic Hoodies:

  • Buy a bigger size. When buying one of these hoodies, think about sizing up for a slouchy look. Sometimes depending on the size, you can even wear your oversized hoodie as a dress.
  • Be creative! Try out lots of different combinations and color combos for success. Think about wearing your hoodie under a blazer or under a long winter coat. The options are endless – you just have to try things out to find out what looks best.

Look 2: Modern Pullover Outfit

Outfit set striped pullover, corduroy pants, boots and jean bag.

Products: Pullover – Urban Outfitters, Jeans – Urban Outfitters, Shoes – Missguided, Bag – Urban Outfitters

This striped pullover is super chill and looks amazing paired with black corduroy pants. Corduroy is very big this fall, so these pants are perfect for this outfit. They can also be cuffed to dress the look up a bit.

Now let’s talk accessories. The low heel boots give this outfit the edge it needs. While any tote bag can match the look, I chose a jean one to play with texture — I love the dark blue next to the gray in the pullover.

Tips for Styling Pullovers:

  • Go oversized for the most of-the-moment look. Right now, it’s all about ’90s inspired pullovers that have a borrowed-from-the-boys feel.
  • Half tuck to show off your shape. If you master the half-tuck, you won’t get lost in a sea of fabric.

Look 3: Cropped Hoodie Outfit

Outfit set with cropped hoodie, jeans, sneakers and white bag.

Products: Hoodie – Missguided, Jeans – Urban Outfitters, Shoes – ASOS, Bag – Urban Outfitters

Finally, this super cute outfit includes a cropped hoodie that is also fitted at the waist to accentuate your curves. It has a corset-inspired look to it, so if you want to wear the matching sweats because you’re not feeling jeans that day, rest assured that you will look cute and put together.

The jeans work well if you want to go out either at night or for brunch and shopping during the day. The all-white platform sneakers give you a tiny boost of height (that I love because of I’m so short) but the all-white pops out. It also matches with the bag, which can be worn around the waist or on the shoulder.

Tips for Styling Cropped Hoodies:

  • Consider the full-on sweats look. This is very trendy right now and looks amazing when you have a cropped hoodie and high-waisted sweats together. The crop of the hoodie makes the look cute, not sloppy.
  • Go with a higher waisted bottom in general. We love wearing cropped hoodies with mom jeans, high-waisted leggings, or even bike shorts for a ’90s workout feel.

A Penny for Your Thoughts…

What do you think of our hoodie outfits? How do you wear pullovers and hoodies? Have you gained any new ideas from this post? Which look is your fave? Let us know with a comment!

Editor’s note: This post was originally published in 2010; it was completely updated and revamped in 2019 with new photos and information.

9 thoughts on “3 Stylish Ways to Wear Your Hoodies and Pullovers”

  1. I have a turquoisey-green pullover hoodie that I really adore, its my go-to item. Can I wear flip flops with it if I wear jeans?

  2. I almost always wear a dress with a zip up hoodie and skinny jeans. The result is a kind of puffy skirt and it looks incredible if I do say so myself. Unique and different!

  3. Great article!

    I love my hoodies from Bilby and Moss (their warmer one with thermal fabric, and the Tali hoodie, perfect for the example that you gave, under a leather jacket). Problem is, I couldn’t come up with creative way to wear them.

    Thanks for the ideas!

  4. This was pretty helpful.
    Where I am, in Sweden, nobody ever wears hoodies to university. I happen to love my sweatshirt and hoodies, but I do feel sloppy when I wear them to lectures… Still, I’ll definitely be pairing mine with a jeans jacket and a floral dress once it gets a bit warmer.

  5. literally yesterday i was thinking about ways to dress up my sweatshirts and then this article came out. it is almost like this website reads my mind because all the articles have perfect timing relative to my life.

  6. This is a very useful post! since 1 or 2 months Ive been buying and wearing hoodies and kind of things very frequently I love layering them I usually wear hodies like the last outfit: on jeans with flats =) also I get some inspiration from these outfits!

  7. This is a great topic. Most college girls that I know have tons of hoodies, and I just love them, but I used to worry that I just looked sloppy and careless when I wear mine. Thanks for showing us how to keep them looking good 🙂


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