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Style Monthly: Sweatshirts

Welcome to a new series on Olivia and Laura that we like to call Style Monthly. In this series, we will show our readers different ways to style a piece of clothing. Today, Olivia and Laura will style sweatshirts!

Sweatshirts are one of the most versatile pieces of clothing we have in our closet and yet most people resort to them for a basic look. Don’t get me wrong, we love a comfy set but why not be comfortable while also slaying street style?

Here are some new go-to outfits to spice up your style with some pieces you already have.

Preppy Frat Boy

This is a personal favorite of Olivia’s because it is super simple to throw together for running errands or even an impromptu picnic in the park. All you need is any sweatshirt and some denim or leggings to pair with it. Next, tie the sweatshirt around your shoulders, and you'll look like the cutest frat boy!

As seen in the picture below, Olivia styled this look with a pair of light wash distressed mom jeans and a plain white tank. She added a pair of delicate hoop earrings and grabbed her sunnies before heading out the door. Simple as that.

This vintage look has been making a comeback in the fashion world and we are here for it!


O+L Fashion Tip: Check the Men’s section

Don’t be afraid to venture into the men’s section for clothing—especially for sweatshirts. Check out H&M for these basic sweatshirts that Olivia wears to death and can be dressed up for street style or worn on a lazy day.


Turtleneck Look

Next up we have the turtleneck look. This styling technique is ideal for the autumn because it allows for layering pieces to keep warm while also putting your hoodie on display. Simply, add a turtleneck or mock neck top underneath an oversized sweatshirt and you’re set to take on the day. You can also dress up this look by adding a pair of slim-fit pants, some chunky necklaces, and heeled booties. Not only will you look super fashionable, but you're also sure to get an insta-worthy picture.


The Half-Zip sweatshirt is another take on the sweatshirt and is a style that can be found in all stores Fall 2020 collection. Ranging from fleece materials to cotton, this is a new take on the sweatshirt. Like the common theme of this article, you can match the half-zip with a pair of jeans or style it with a pair of biker shorts and chunky sneakers and be the next Artizia model. We love the half-zip because it can go from après ski and super chic depending on how you style it.

Cool Girl Vibe

Want to be a cool girl? Just follow this look. Grab a crew neck sweatshirt (do the tuck--instructions below) and match it with a pair of mom jeans. However, were going to refine this outfit by throwing on a pair of strappy sandals or mules with a denim jacket. This following step is crucial: slick your hair back into a low bun or ponytail and look unbothered with a pair of large sunglasses. Voila, the easiest yet super fashionable look that will make all heads turn.


O+L Fashion Tip: The Tuck

The Tuck is a technique used to take a regular sweatshirt into a cropped one that accentuates the waist and provides for a more put-together look. In doing so, you can now style a sweatshirt with any pair of jeans, a skirt, or even some matching sweatpants.

All you have to do is tuck the hem of the shirt into your bra and from there you can decide how short you want the sweater to be.



The perfect way to dress up any sweatshirt or hoodie is with layers. Layer an oversized hoodie with a blazer on top for a business casual look. As seen on Emma Leger (@emmaleger), this is the perfect way to transition summer whites into fall.

Another way to style a sweatshirt is to layer a longline or trench coat over top. Elevate a more casual look by styling a sweatshirt with your favourite pair of faux leather leggings and a coat to complete the look. Viviane Audi (@vivianeaudi) brings this look to life with a cropped grey sweatshirt and checkered plaid coat.

Our absolute favourite way to layer sweatshirts is with leather jackets. A leather jacket is a fall must-have and can be worn with almost anything! Layer it over a sweatshirt or hoodie thrown on a pair of denim jeans and accessorize for the perfect basic fall outfit. Phoebe Gore (@pheebslfashion) does just that and we are obsessed!

As a Dress

An oversized hoodie or sweatshirt is a staple in every girls’ closet! Tired of wearing it over leggings or biker shorts? Us too. Style your oversized sweatshirt as a dress next time! Sophie Suchan (@sophiesuchan) wore a white oversized hoodie as a dress and layered on a cute velvety pink bomber jacket for a pop of #PFG.

Similarly, Emma Leger (@emmaleger) styled this oversized white hoodie with a leather jacket and some black nylons for cooler fall weather. Both looks can be completed by some chunky sneakers and cute sunnies!

With a Skirt

Tennis skirts have been all the rave this summer and are even transitioning into fall fashion. Now that the weather is cooling down and fall is approaching, we see content creators styling tennis skirts with a sweatshirt and we are here for it! Stunning queens Emma Leger (@emmaleger) and Sophie Suchan (@sophiesuchan) styled their tennis skirts with a layered sweatshirt and collared shirt combo. Emma’s Doc Martens are giving us all the fall vibes. Maddie Briell (@maddiebriell) does the same with this super cute graphic sweatshirt from H&M.

Another way to dress up a plan sweatshirt is with a mini skirt. Josi Pellicano (@josipellicano) pairs her white sweatshirt with a cute patterned skirt for a day out! Complete the look with a gold chain, sunnies and your favourite sneakers.

Here, Viviane Audi (@vivianeaudi) styled a denim mini skirt with a fun embroidered sweatshirt. Perfect for that summer to fall transition!


Hopefully, your takeaway from this article is that sweatshirts are multi-purposeful! They can be paired with almost anything and, depending on how you accessorize it, you can bring any look from day-to-night. So, keep on buying sweatshirts—you can even own one in every color like Olivia and Laura, just don’t forget to try something new. Use this Style Monthly article to enhance your usual looks. Oh, and don’t forget to tag us and use our hashtag #OliviaandLaura when you do!



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