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5 Cute Ways to Style a Sweatshirt

Jan 14, 2021

5 Cute Ways to Style a Sweatshirt

Happy almost Friday! 

It feels good to be back with a little styling session today. I feel like I have been thrown out of my groove for so long with…everything. But today I felt a little wave of productivity and I know getting dressed in a cute outfit, as silly as it sounds, always makes me feel better. So that’ what we’re going to talk about today! Specifically–how to style a sweatshirt! 

I think sometimes sweatshirts can get put in the “not versatile” category because they’re casual, so we typically only think to pair them with leggings, but a sweatshirt like this can be really versatile, too! Today I’m sharing a handful of cute ways to style this sweatshirt (or any sweatshirt like it–this will absolutely work with any tunic-length sweatshirt in your closet!) 

5 Cute Ways to Style a Sweatshirt

Featured staple of the day: This $33 (on sale!) Cowl Neck Tunic Sweatshirt!

It is SO soft and comfy without being too thick (so it’ll be a great layering piece during the spring too!) I loved the cowl neck detail, and I don’t have a longer length sweatshirt–I especially like the length because it looks cute with leggings! Comes in so many colors–love the olive green and camel too! 

Sizing: TTS, I got a medium so it would be cozy/oversized, but small would’ve worked too!) 

Now, let’s get into the outfits! 

Quick shop items in today’s looks: 



The classic: Jeans + Sneakers: 

5 Cute Ways to Style a Sweatshirt

Let’s start out with a classic look–a cute sweatshirt with jeans and sneakers!

The jeans: These are the AE mom jeans I won’t shut up about–I’m hesitant to use the word “pandemic jeans” because I definitely went through a phase where I was like, WHO IS WEARING JEANS RIGHT NOW!? But sometimes I just can’t take it anymore and I NEED to wear normal clothes to feel like a normal person again, and that is when I reach for these jeans. They are incredibly soft, (think more cloth-like than rigid denim), high rise, most importantly, not tight. I adore them and wear them often. I also love that they come in regular, short and tall! 

Sizing: TTS, I take a size 4. 

The sneakers: Old standbys, I wear these in all seasons and have had them since they came out a year ago. I reach for these often because they’re classic, comfortable (didn’t require any break-in) and they’re leather, so they wipe right off and are easy to clean. You can see my review on them here

Sizing: TTS

Now, this look might be a little too tomboy for some, so next I’m going to share how to make it a little more classic/preppy with the addition of a few accessories! 

Prep it up: 

5 Cute Ways to Style a Sweatshirt

You know how I talk about the juxtaposition rule a lot? This is a great example! If the above look was a little too tomboy (sweatshirt, ripped jeans, sneakers may feel a little TOO much for some that gravitate toward more classic/preppy or feminine styles)–then you just have to play the opposite game! 

What’s the opposite of edgy tomboy? Classic preppy! Okay–what can we add that is classic/preppy? A Barbour coat, and a plaid scarf! (Plaid scarf is so old, but this cream and camel check scarf is very similar!) 

Barbour Polarquilt Beadnell: ON SALE for 25% right now which never happens! 

I have had this coat for several years now and it’s always a staple, especially in the shoulder seasons (fall and spring). It’s a great winter coat for milder weather and I would say it’s warm enough for the warmer Chicago winter days. (We’re talking a walk when it’s 35+ degrees.) It’s lined with polar fleece to keep you toasty and I love the classic design that never goes out of style. Right now most of their sizes are fully stocked (which is shocking giving the amazing price). 

Sizing: Barbour runs small, and note the differences between US/UK sizing–I typically wear a size 4 or 6 jacket in Barbour (4 if I want it more formfitting, 6 if I want room for layers). The one I’m wearing here is a 4 and I like the way it fits but if I wanted to wear a lot of thick layers underneath I would need to go up to a 6. Just a personal preference! 

Cozy (Zoom-friendly) WFH outfit: 

5 Cute Ways to Style a Sweatshirt | little slipper mule sneaker shoes

Did you REALLYYY think I wasn’t going to sneak the Aerie leggings into this post somewhere? ???? Of course not. The best leggings in ALL THE LAND. They were one of my favorite purchases in all of 2020, and as a result became one of my top sellers in all of 2020 because of their incredible price and the fact that they feel JUST like Lululemon’s Align leggings for just $26. Plus, I think they come in way better colors. (I love this sweatshirt especially with the olive color!) 

Sizing: TTS! I have smalls 

Then there are these little slipper mule sneaker shoes (TBH I don’t know what to call them, but I DO know that they are great WFH shoes.) They are sherpa lined on the top making them super cozy, but they’re also like, you know, real shoes? So I very much appreciate that! I love the rich cognac color too which looks good with almost every other color! Come in black and leopard as well! 

Sizing: TTS! 

little slipper mule sneaker shoes

A “Finally Leaving the Home” look: 

thick wool socks

We’re saving my favorite for last, because I relish ANY opportunity to put on REAL CLOTHING these days! This is a great cozy outfit to wear, say, when it’s above 35 degrees in Chicago and Neal and I decide to treat ourselves to a socially distanced Igloo happy hour. 

The boots:

Let’s discuss the boots first because they’re new. Neal and I discussed these are a little edgy than something I’d normally wear but he was like “I’m here for edgy Jess” and I feel like the pandemic is really inspiring me to break out of my usual style zone. ???? Anyway, I had really loved the look of the Madewell version, but I found these for half the price AND they’re waterproof! (Not to mention they’re from Nordstrom so I knew if they didn’t end up being my thing, it was fine because their return policy is the best thing ever.) They are also water-resistant and have really great traction which makes them very practical for the midwest! 

Sizing: They run TTS. Note, I do think they’re best with some substantial socks (at least for the first few wears). I wear them with these thick wool socks (they’re actually the wool socks I got for hiking earlier this year) and they work perfectly. 

The jeans:

You’ve heard me rattle on and on about these–the Old Navy warm jeans! They are so comfortable, so soft and cozy–they’re lined with a lightweight fleece material. So they keep you so warm, but they don’t feel too thick or overwhelmingly hot when worn inside. (I wear mine all day inside and have no problems.) Truly magical, and affordable, too!

FYI–The black color is also a very dark black, and I recommended them to a reader who is a teacher going back to school but needs professional looking clothes that will keep her warm with all of the windows open! I knew these were the pants for her! If you’re also needing some warm professional-looking pants, definitely look into these!

Accessories: TBH when I put this beret on I felt more like my normal self than I had in months and it made me so happy. ???? My color is sold out (brand is Halogen) but they still have more colors available and they’re my favorite berets! (I have a few colors!) Scarf is very old but similar here

Sizing: They run TTS. The pants I’m wearing here are 2’s but they’re snug and the 4’s (my new “pandemic” size) fit much better (I have 4’s in a different wash). 

thick wool socks

(Here’s an up-close look at the boots. Ignore the lint on my pants! ????) 


Hope you liked today’s style session whether it introduced you to some new wardrobe staples or just inspired different ways to shop your closet! 

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