How to Style Streetwear for the Fall Season

How to Style Streetwear for the Fall Season

As fall comes around, many of our social feeds become flooded with photos of our followers in orange-colored cardigans, dark brown combat boots, and of course, a Starbucks coffee in hand. This is what the majority of our society defines as “the fall aesthetic.” 

It’s often seen as the perfect time to be cozy and match the colors of the season; however, in return, you end up “twinning” with everyone else around you. But what if you want to maintain your style? What if your style is primarily streetwear and inherently the opposite of the fall aesthetic? Well, luckily, there are still options. Styling streetwear can be challenging, but not impossible. So if you’re looking for some tips this fall, keep reading!

Find Alternatives for T-Shirts

Just because the temperatures are cooler doesn’t mean that we can’t wear our beloved t-shirts. T-shirts are a staple in streetwear fashion and although they are worn most often in summer seasons, there are actually great ways that you can make them work for the fall as well. 

Photo sourced from Prophet NY

Instead of any low-price, lightweight t-shirt you may already have in your closet, try opting for one with a little more weight to it. Not only will this provide you with some additional warmth during the colder months, but you will also find that the heavier the shirt, the more wear you will get out of it long-term. Luckily, many basic streetwear t-shirts come in a heavier fabric or at the very least, an oversized fit—allowing you more coverage than a standard shirt. However when you add more weight, you typically risk sacrificing breathability; which isn’t ideal especially if you decide to layer. Luckily, t-shirts like those from Prophet New York are both high-quality and made of jersey fabric, which is known for being one of the best fabrics to wear in hot, summer months as well. Finding this combination of durable material that maintains its breathability is rare but as the fall months come around, you’ll be so happy with your choice now and in the future.   

If you already have a few heavy-weight t-shirts in your closet, you may choose to try out layering during the fall and winter months. Layering in streetwear can actually be done a little differently than you may think. Instead of wearing the standard jacket and sweater over a t-shirt, play around with proportion, contrasting styles, and accessories when you layer. A great example of this type of layering was seen in the ever-popular corset trend that took over fast-fashion in 2018. By adding a corset to the top of any short or long-sleeved shirt, simple t-shirts were immediately seen as unique streetwear fashion and even high fashion. Today, given the many types of corsets to choose from, you can still use this as a way to layer. Try going for a similar style bustier over a t-shirt and add a jacket on top. By doing so, you’ve found a way to keep warm without sacrificing your style.

T-shirts are one of the most common wardrobe pieces out there so regardless of the season, it’s  important to find ways to make them work in your streetwear year-round.

Try Cozy Accessories

During the cooler months, accessories are your best friends in the world of streetwear. For both men and women, hats, among the many other accessory options, can take just about any basic outfit to the next level. 

Woman in Lilac sweater and hat
Photo sourced from ASOS

One may argue that with a cute hat you have endless possibilities. If warmth is your priority, then beanies are where it's at. Beanies can blend into any fall outfit or, you can allow it to be the focus of any streetwear look. Asos, for example, has the perfect statement beanie in a bright, lilac color, sherpa-esque material, and fisherman style. Very different from what you would typically expect a beanie to look like but nonetheless, it will complement any fall, streetwear style.

If a beanie isn’t really your speed, a trucker hat may be a better fit given their trendy nature in 2022. Trucker hats literally get their name from being a popular hat choice for truck drivers. However, in the last couple of years, they’ve made their way into streetwear style and have become the perfect way to tie together any outfit. In the fall season, trucker hats can not only add to any outfit but they can also add to your layers to keep you warm. Trucker hats and hoodies are a streetwear staple and in the fall specifically, the combination of the two may be exactly what you need to stay warm and on trend.

Find the Perfect Fall Sneaker

Sneakers are always a must-have. Regardless of the time of year, it’s important to find a shoe that will tie any outfit together. However, in the fall specifically, we are often faced with weather conditions that are less than ideal for our beloved sneaker collection. Rain, mud, and even snow in some places can ruin any shoe over time. This is why it's so important to be intentional with your sneaker choice and find one that maintains its practicality in tough weather conditions. 


Platform sneakers, for example, are great options if you want to avoid messy weather without having to bring out your winter boots. By allowing some extra space between the ground and the details of your sneakers, they are perfect for fall walks or activities. One of my long-time favorite platform sneakers have been the PUMA Creepers by Rihanna. They are a simple, staple shoe that give you plenty of lift off of the ground. If you’re looking for something a little bolder and popular in current streetwear fashion, you may want to try Converse’s Run Star Motion CX Platform Sneaker.

Converse sneakers
Photo sourced from Converse

The sneaker has a pretty funky look that incorporates its thick sneaker treads into the actual style of the shoe. You’ll no longer have to worry about choosing between style and practicality and instead, you can have both.

Another great sneaker style that is also mindful of messy fall weather is leather shoes. Leather, of course, is not new to the world of fashion and has always been very popular when it comes to fall boots, jackets, gloves, and other accessories. However, sneakers aren’t often thought to be a part of the leather trend. This season, you can make the point splurging a little to find that perfect, fall sneaker. High-fashion brands like Amiri mimic the Nike Dunk sneaker silhouette in their leather Black Skei sneaker.  But, you can also find leather versions of common, everyday sneakers like Converse’s high-tops, Vans’ classic slip ons, and more.

Don’t Be Afraid of Bold Outerwear 

Now, would it really be the fall season if we didn’t talk about outwear. Jackets and coats are my personal favorites when it comes to fashion and in the fall especially, you can showcase a bold jacket along with other great streetwear pieces and still be warm.

But the colder and colder it gets, the higher we zip our zippers, and the faster our outerwear becomes one of the very few pieces you can actually see in our outfits. This is why it is important to think big with your outerwear this fall.

The perfect way to take your coats and jackets to the next level is with the use of prints. Whether it's an all-over camouflage puffer coat or one, simple print on a denim jacket, you can instantly bring life to a basic silhouette with the use of print. 

Black jean jacket with Frankenstein on the back
Photo sourced from UO

By going with a printed coat or jacket, you can also bring your own unique twist to layering. In the photo above, you can easily pair this Urban Outfitters Monster print jacket with a basic, black turtleneck, black jeans, and combat boots. This is an outfit we’ve likely all seen in some way or another but because we have the addition of the print, you can wear it in a way that is unique to you.

Similarly, you can take a chance on your outerwear through the use of color. Bold color clothing pieces in general are not unheard of but during the fall season, you typically see people sticking to standard, autumn colors for their outerwear. So, if you are the person to take a chance on color, you’re bound to stand out for your one-of-a-kind style without sacrificing your comfortability. 

Lastly, playing with texture is one of my personal favorite ways to bring style to any streetwear look. It shows attention to detail and subtly makes any piece a statement piece. However with outerwear specifically, incorporating texture allows you to maintain a lot of other practical needs and still show your sense of style. For example, one of my favorite Louis Vuitton pieces, the Monogram “Boyhood” Puffer Jacket takes an everyday, wearable color like gray and adds that extra detail to it through texture. Even aside from designer pieces, more wearable fast fashion brands are starting to incorporate different vinyl, faux fur, and sherpa textures into their clothing this season so be sure to take full advantage where you can. 

The fall season is upon us and whether we like it or not, we will have to adjust our wardrobes to fit the cooler weather. However, in doing so, you shouldn’t have to sacrifice your style. Naturally streetwear as a style contains many pieces that are fit for summer in particular. Thankfully, however, with these styling tips, we can take advantage of the many options of shirts, accessories, sneakers, and outerwear available to ensure we can dress as ourselves in every season.

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