Fresh to Death: Mastering The Art Of Comfy Streetwear Aesthetic Looks

Rockin' the streetwear aesthetic is perfect for anyone who loves to keep it comfy and fresh. The laid-back attitude of soft, loose-fitting garments balances intention and effortlessness in an undeniably cool way. Rooted in the skate culture of the ‘70s and '90s, streetwear has evolved to encompass a diverse range of styles, all unified by a commitment to comfort and individuality.

Streetwear aesthetics are a culmination of historic roots and reflection of contemporary pop culture. Originating from the surf and skate culture of Southern California in the late 1970s and early 1980s, it’s a cool instance of fashion trends igniting from the bottom-up. Brands like Stüssy began by making surfboards and eventually started producing graphic tees that became popular among surfers and skaters. As skate culture grew, so did the influence of streetwear, eventually incorporating elements of hip-hop, punk, and Japanese street fashion. Today, streetwear is a global phenomenon, blending high fashion with everyday casual wear.

In this blog, we’ll explore key elements of the streetwear aesthetic and share our top tips for styling a streetwear look. From comfortable, functional outfits to quality fabrics, oversized silhouettes, and thoughtful layering, we’ll cover it all. Plus, we’ll delve into athleisure streetwear, the fun element of playing with styles, the art of juxtaposing high and low fashion, and the impact of sneakers and hats. Bringing the drip home: we’ll talk about adding your flavor to your style so you can step out feeling fire.

Comfortable, Functional Streetwear Aesthetic ‘Fits:

When form and function squad up, streetwear’s where it’s at. It’s all about turning your comfiest gear into straight fire and making sure your favorite looks stay cozy. The key to streetwear? It’s all in the fit—loose, breathable, and functional.

For example, a matching sustainable hoodie and jogger set not only looks cohesive but also feels comfortable AF. Look for hoodies with soft, plush interiors and joggers with adjustable waists and multiple pockets for that functional element. Streetwear walks the line of activewear, allowing for optimized performance and style– more functional elements might include moisture-wicking and breathability. Notice what is best for your personal comfort preferences as you start pulling together your base staples. Starting with those comfy basics, add a great pair of sneakers and a cap… and there’s your look! This is a great place to start and works for men and women alike. It’s a pretty simple recipe on the surface, but the secret sauce to the look is all in the details.

Quality Fabrics

Given the comfort-driven nature of the streetwear aesthetic, the quality of your materials can make or break both the look and your experience in it. So, get to know those soft materials, and which ones feel most delicious to you. Cotton, fleece, or jersey can be great. And of course, we recommend looking specifically for sustainable options. Organic cotton, recycled polyester, and bamboo or sustainably farmed plant based fiber and wood pulp fabrics are excellent choices you might notice when you start reading those tags. Eco-friendly fabrics are not only less harmful, but the quality ensures your garment will stick around longer (even the ones you’ll never want to take off).

Oversized Silhouettes

Adding more to that concept of comfort, the streetwear aesthetic tends to favor baggy looks over anything super form-fitting. This is where your favorite, loose-fitting loungewear gets a moment in the fashion spotlight. It’s totally okay to a have baggy-on-baggy streetwear look, just consider the element of layering to pull it off in a really stylish way. This will add depth to your outfit and help the look feel just put-together enough, rather than a culmination of the first things that fell out of your closet.

For instance, you can start with an oversized graphic tee, reach for a pair of wide-leg pants or harem pants, and an overcoat or oversized bomber jacket. The key is to play with proportions and textures to create some visual interest in the ensemble– even with the baggy garms.

If you do like a more balanced silhouette, consider pairing oversized and fitted pieces together. For example: a loose-fitting hoodie with cargo pants that have a tapered ankle for a sleek yet relaxed look.

More About those Layers:

This is gonna be a key differentiator as we walk the fine line between ‘fire streetwear look’ and ‘just rolled out of bed’. One way to play with this is layering an oversized t-shirt over a long-sleeve henley shirt or thermal for that nostalgic nod to 90s skate culture. And of course, play around with those jackets: bomber jackets, trench coats, denim jackets, hoodies, and windbreakers are great for layering. They add dimension and style to any athleisure streetwear outfit.

When it gets chilly, layering jackets or vests over hoodies is the move. You’ll stay warm and comfy while looking effortlessly cool. Throw in some accessories like beanies, scarves, and fingerless gloves to complete that streetwear aesthetic vibe and keep cozy.

Getting Matchy-Matchy:

A foolproof way to nail a athleisure streetwear look is to make it a set. Matching tops with bottoms or pants with outerwear gives the comfiest clothes a purposeful vibe. Streetwear is marked by the use of neutral colors (black, white, beige– whatever calls you) with some occasional pops of color or shine. Investing in great neutral basics and staples can be a great way to start curating your streetwear wardrobe. From there, you can mix-and-match from an easily pairable set of options. And of course, with your cool, comfy canvas, start building upon the look with interesting accessories and statement pieces.

Get this on lock by starting with a set in your favorite classic neutral color, like that solid black hoodie paired with matching joggers. From there, build up your look by layering on the style. Throw on a bright red bomber jacket to add a splash of color that pops, or accessorize with a standout belt and limited-ED sneakers featuring bold accents. These additions not only elevate your outfit but also add that extra edge to your streetwear game.

Lean into Athleisure Streetwear:

Streetwear and activewear go hand-in-hand because both aesthetics are built around the ability to comfortably move your body and easily transition throughout your day. Athleisure streetwear takes elements from clothes you might see at the gym like joggers or sports bras, and introduces some fashion intention for a look that ends up being super cool, sporty, and packs a bit of an edge.

For a great women’s athleisure streetwear outfit, consider pairing high-waisted leggings with a cropped hoodie. Add a pair of sleek running shoes and a sporty cap for a look that’s both functional and fashionable from the gym to lunch. And for men, combining a moisture-wicking tank with stretchy tapered pants and a lightweight windbreaker can create a versatile outfit that works for both workouts and casual hangs.

Have fun with styles:

The streetwear aesthetic often brings to mind hoodies and logo tees, but there’s plenty of room to experiment with unique styles and silhouettes. Try drop-crotch shorts, vintage-style swim trunks, or jogger shorts for a fresh take on streetwear. Cargo joggers offer a cool streetwear aesthetic with a sweatpants feel. And, as always, pairing any of those bottoms to create a matching set is a solid choice.

Experiment with different lengths and cuts. For example, those drop-crotch shorts could look really cool with a longline tank top and an oversized flannel shirt. Add some high top sneakers and a beanie and the look takes on a quintessential laid-back, skateboard hipster vibe. Vintage-style swim trunks can be paired with a retro graphic tee and slides for a relaxed summer surfer look. Don’t be afraid to mix patterns and textures—this can add a unique twist to your ‘fit.

Juxtapose ‘High’ and ‘Low’:

The streetwear aesthetic is known for mixing high and low fashion. Elevate a comfy base with some jewelry or a great bag. Don’t shy away from statement accessories, which can add an extra touch of personality to your look.

For example, pair a basic white tee and joggers with either something like a high-end designer cross-body bag, or some unique eye-catching jewelry. Layering a gold chain necklace or adding a statement watch can instantly elevate a simple outfit.

Sneakers and Hats, Hats and Sneakers:

Sneakers are essential in streetwear, and if you're deep into the culture and community, it's a pretty dope hobby too. Whether you're a hardcore sneakerhead or just starting to vibe with the streetwear aesthetic, make sure to pick kicks that blend comfort with serious style. Your feet are prime real estate to express your personal swag in a streetwear getup. And hats? From caps to beanies, they're key in completing your look with your own signature style.

High-top sneakers, like the classic Converse Chuck Taylors or Nike Air Jordans, are iconic in streetwear. Pair them with cuffed joggers or rolled-up pants to show off the kicks. Try a boot style sneaker with an oversized hoodie. Hats, whether snapbacks, fitted caps, or beanies, add a finishing touch to your outfit.

Personalize Your Streetwear Aesthetic Look:

The deal with streetwear is, a dope outfit might not hit right if you don't add those personal touches to really make it yours. Consider adding some unique jewelry– we love this gender-neutral ear cuff. Another great idea here is to hunt for vintage graphic tees that reflect personal interests or cultural references. Head to the thrift store or online marketplaces with an eye out for graphics featuring your favorite bands, movies, or slogans. And don’t be afraid of a little DIY. Customize your denim jacket with patches from places you’ve visited or pins that represent your hobbies and interests. Personalizing your streetwear not only makes your outfit unique but also tells a story about who you are.

We hope this helped you get hyped about your athleisure streetwear, inspired to rock that comfort, and wear what vibes with your soul. The streetwear aesthetic is all about showing off your true self while keeping it chill and comfy. Whether you're throwing it back with some '90s-inspired layers or mixing designer pieces with thrift store gems for that high-low steez, the streetwear aesthetic's got you covered with endless ways to express yourself. Remember, there's no rulebook in this game. You do you, fam. The streets are your runway, so experiment, push boundaries, and most importantly, wear what makes you feel like the main character. Keep your eyes peeled for new trends, but don't be afraid to put your own spin on things. That's how legends are made in the streetwear world. So go ahead and curate that closet with pieces that make you feel like a straight-up boss. Your future fly self will thank you when you're effortlessly serving looks in any situation, no cap.