5 Ways To Make Hoodies Feel A Little More Chic

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Hoodies have been the star of my closet since, well, I started picking out my own clothes as a child. While I used to reserve them for sports practice and weekend lazy days, it occurred to me as I got older that I could easily rock these for everyday outfits. Hooded sweatshirts can actually be cute, and they have had quite the glow up in my personal wardrobe over the last decade.

I specifically remember a moment standing in my closet as a teenager, looking at all of my sweatshirts and thinking “wow, it’s time I grow up and buy real clothes.” I was sad, yet determined to wear Grown-Up Outfits, which in my mind probably meant button-ups, uncomfortable tiny sweaters, and certainly nothing with a graphic on them.

Flash forward to me as a twenty-something-year-old, standing in my closet, looking at all my sweatshirts, thinking “it’s time I stop fighting this and just embrace my own style.” That inner confidence of owning what it is that I really love, something that I think many of us experience as we enter adulthood, was growing. I no longer cared what grown-ups were supposed to wear!

These 5 go-to tricks for making a fave hoodie feel more fun & chic can spruce up any sweatshirt: fitted, oversized, cropped, long — or heck — even a crewneck (although I prefer a big hood visually…& for comfort).

hoodie | blazer | jeans | socks | sneakers

How To Style A Hoodie: 5 Steps For Elevating This Cute Sweatshirt

I treat a hoodie just as I would a sweater in my closet. I wear them alone (not on top of a t-shirt like I would in high school) so the fabric can drape as it was intended, eliminating the appearance of extra bulk that can sometimes occur when layering. 

While my personal style leans towards oversized hooded sweatshirts, all these tricks I share below can spruce up any sweatshirt: fitted, oversized, cropped, long, or heck — even a crewneck sweatshirt (although I do prefer a big hood visually…and for comfort). No matter your preference, these are my five go-to tricks for making your favorite sweatshirt feel a little more fun and chic.

1| Start With A Tuck

These 5 go-to tricks for making a fave hoodie feel more fun & chic can spruce up any sweatshirt: fitted, oversized, cropped, long — or heck — even a crewneck (although I prefer a big hood visually…& for comfort).

hoodie | jeans

Perhaps the quickest way I rock a hoodie that feels a little more styled and less frumpy? Simply tucking it in. Depending on the sweatshirt and the pants I’m wearing, I tuck one of three ways. The first way is a simple half tuck (or “the French tuck”) into my jeans. I find it’s actually easiest with a longer sweatshirt than what I’ve got here, as I have more fabric to work with and results in a really good drapey look in front. 

The second way I love to tuck my sweatshirts (this goes for t-shirts, too), is up into a longline bra. This is also my go-to option if my jeans are on the tight side, or when wearing leggings and bike shorts.

hoodie | jeans

The second way I love to tuck my sweatshirts (this goes for t-shirts, too), is up into a longline bra. With a good longline bra that has a strong elastic band and/or a sports bra built into it, the bottom edge of your sweatshirt can be tucked up underneath. This option is great if I’m wearing a cropped sweatshirt, shown above, and gives a cleaner line then the half tuck (almost tricks you into thinking it’s fully tucked into my jeans). This is also my go-to option if my jeans are on the tight side, or when wearing leggings and bike shorts.

The third tuck is simply tucking the entire sweatshirt in. I love this for underneath blazers and/or if the sweatshirt is especially oversized for something fun and unexpected.

Favorite Longline Bras for Tucking


2| Add Some Jewelry  

More specifically, I love wearing hoops with my hoodies with my hair pulled back to show them off.  I personally feel a bit more put together and "ready" for the day with some on, and I love wearing simply all gold or all silver pieces.

earrings | hoodie

Never underestimate the power of a few pieces of jewelry. I personally feel a bit more put together and “ready” for the day with some on, and I love wearing simply all gold or all silver pieces. More specifically, I love wearing hoops with my hoodies with my hair pulled back to show them off.

This pair is a great alternative for a major brand that celebrities like Hailey Bieber rock, they’re much more affordable. These earrings are also unbelievably light and comfortable. 

More specifically, I love wearing hoops with my hoodies with my hair pulled back to show them off.

earrings | hoodie

I’m very sensitive to jewelry, and the first day I put these on I accidentally wore them to bed. I didn’t even realize until multiple days later that the earrings were still there, on my ears. SO GOOD! I’m wearing the 20mm but also have the 13mm for something a bit more subtle (ironically the 13mm are not as comfortable to sleep in). 


3| Layer Underneath An Oversized Blazer

This Boyfriend Blazer from Good American is totally fun (and I want to wear it just like the model come summer). It’s actually quite huge, and I could have chosen a size down, but I decided to keep it since the extra oversized vibe felt totally me. 

hoodie | blazer | jeans

I’ve been on what feels like a never-ending hunt for a good oversized blazer. This Boyfriend Blazer from Good American is totally fun (and I want to wear it just like the model come summer). It’s actually quite huge, and I could have chosen a size down, but I decided to keep it since the extra oversized vibe felt totally me. 

The hoodie + blazer paired together is such a good juxtaposition of casual and formal, resulting in a “sophisticated yet still down for a good time” sort of vibe -- especially with the oversized hood layered on top.

hoodie | blazer | jeans | socks | sneakers

The padded shoulders are not only an awesome retro vibe, but actually aid in the comfort of wearing hoodies underneath. With or without shoulder pads, though, I do recommend finding a blazer that is somewhat oversized to accommodate layering it over a hooded sweatshirt.

The two paired together is such a good juxtaposition of casual and formal, resulting in a “sophisticated yet still down for a good time” sort of vibe — especially with the oversized hood layered on top.

For a blazer that is still oversized but with a slightly more feminine silhouette, The Boss Blazer also from Good American looks so good (bonus, it isn’t as expensive)! 

hoodie | blazer | jeans | socks | sneakers

For a blazer that is still oversized but with a slightly more feminine silhouette, The Boss Blazer also from Good American looks so good (bonus, it isn’t as expensive)! 

Fit notes: Good American sizing for this blazer is split into specific categories, with a S/M or L/XL being the two I had to choose from (there’s sizes smaller and larger than those, too). A size M/L is what I would consider my “true size” but since that wasn’t an option I went with a L/XL, or what’s referred to as a 2-3 on their website. If you’re in-between sizes like me, you can certainly size down and still get that oversized look.

More Blazers To Rock With a Hoodie


4| Pair With Vegan Leather Pants

These 5 go-to tricks for making a fave hoodie feel more fun & chic can spruce up any sweatshirt: fitted, oversized, cropped, long — or heck — even a crewneck (although I prefer a big hood visually…& for comfort).
While some may reserve vegan leather pants for dressier blouses and heels, I love them with a hoodie. Since vegan leather pants also look a little more fancy than denim, it’s the perfect pairing to your hoodie and sneakers when looking to style up an outfit.

hoodie | pants | sneakers

While some may reserve vegan leather pants for dressier blouses and heels, I love them with a hoodie. These pants often come with a cozy soft lining, making them a much warmer option than denim when the weather is cold. Since vegan leather pants also look a little more fancy than denim, it’s the perfect pairing to your hoodie and sneakers when looking to style up an outfit.


5| Pick Other Outfit Pieces In The Same Color Tone

Starting with a favorite pair of jeans (of any color/wash), I love to grab a jacket and sneakers (even paying attention to my socks) in the same color tones as my hoodie and get an equally New York-street-style effect! 

hoodie| jeans | shacket | sneakers

This one is perhaps most easily done with the color black, as black denim, a black hoodie, black boots, a black jacket, etc., all paired together is effortlessly chic. But it can be well-executed with other neutrals we have in our closets, too. Starting with a favorite pair of jeans (of any color/wash), I love to grab a jacket and sneakers (even paying attention to my socks) in the same color tones as my hoodie and get an equally New York-street-style effect! 

Starting with a favorite pair of jeans (of any color/wash), I love to grab a jacket and sneakers (even paying attention to my socks) in the same color tones as my hoodie and get an equally New York-street-style effect! 

hoodie| jeans | shacket | sneakers

A Nod To Gap’s Vintage Soft Cropped Hoodie

The sweatshirts I’m rocking are both Gap’s Vintage Soft Cropped Hoodie in regular length (for anyone worried about a long torso, you can grab it in a tall). It’s available in over 10 colors and new seasonal colors are often knocking older ones on sale for a real score to scoop up. The hoodie is super-soft, lightweight yet still warm, and hits right at the top of all my high rise jeans. I especially love that it doesn’t have a front kangaroo pocket. While those can be fun (and I own plenty), it’s easier to tuck in a hoodie without that pocket, which helps with styling. 

Fit notes: The sweatshirt runs slightly big, I’m wearing a large in the grey and a medium in the taupe. The length between the two sizes is pretty much the same, maybe a half inch difference or even less, but the drapey silhouette definitely gets bigger as you go up in size which I love.

Xx,
Amy

Let’s be friends on Instagram! Sharing life from my sleepy little beach town, daily style, makeup favorites, Gilmore Girl binge-athons, and endless cups of coffee – all with a good dose of adorable toddler content, too.