Top 3 Stylish Streetwear Looks for Fall

Streetwear centers on comfortable clothing and accessories like jeans, T-shirts, baseball caps, and sneakers.

I often get inquiries about comfy and casual styles, so it’s time to showcase some standout streetwear looks to elevate your Fall wardrobe. If you search for fashion trends on Google, there’s no doubt this one will rank in the top 5. You’re likely seeing it all over your social media feeds daily. And let’s not overlook the “Rich Mom” trend—it absolutely belongs in the streetwear category!

To truly elevate your look, there’s a definitive way to wear these styles. You definitely don’t want to appear like a teenage boy who just rolled out of bed; instead, styling is essential. Your hair should be styled, accessories are crucial, and slim sneakers are a must. Beyond athleisure, this is my go-to look, as it combines both comfort and chic sophistication effortlessly.

I’ve highlighted my top 3 ways to wear this trend below.

Over-sized trenches with trousers exude style and confidence. Layer a simple T-shirt or sweater beneath for a chic touch. Finish the look with stylish sneakers and a baseball hat, and you’ll absolutely own it! Petite ladies, embrace this trend fearlessly—this style is for everyone, and you can definitely pull it off!

I scoured Amazon to find my favorite trenches, trousers, sneakers, and baseball caps.

“As an Amazon Associate, I earn from qualifying purchases.”

Oversized Wool Blend Trench
Chocolate Brown Belted Trench
Double Breasted Long Trench
Windproof Long Trench
Single Breasted Windproof Trench
High Waisted Wide Leg Trousers
Casual Wide Leg Trouser
Burgundy Trouser
Carhartt Baseball Cap
Roxy Baseball Cap
Yankees Ball Cap
Samba Messi Shoe
Veja Volley Sneaker

Wide leg denim continues to trend (yay 90’s), and can be worn with a T-shirt and blazer, a cropped button down, or my favorite addition to the season- a cool sweater vest with a button up layered underneath.

I’ve highlighted my favorite Amazon finds of wide leg denim, sweater vests, and the best button ups for layering.

Wide leg Black Denim
Cuffed Wide Leg Denim
Mom Jeans
White Button Up
Black Button Down
Cable Knit Sweater Vest
Plaid Geo Vest
Oversized Sweater Vest
Crew Neck Sweater Vest

Another key look this season- a puffer vest layered over the top of your favorite athleisure styles. Think yoga pants, joggers, or full jumpsuits which is what I am loving right now! Jumpsuits are amazing layering pieces. You can also throw a cropped sweatshirt over top for another sporty chic look.

Here are my favorite finds on Amazon to create this look.

Oversized Puffy Vest
Red Puffer Vest
Lightweight Zip Up Vest
Long Puffer Vest
One Piece Bodysuit
Loose Romper
Flare Jumpsuit
Square Neck Jumpsuit
Cropped Sweatshirt
Cropped Hooded Sweatshirt
Cropped Zip Up Sweatshirt
Oversized Cropped Sweatshirt

As you likely already know, I am absolutely passionate about a wardrobe that allows for endless mixing and matching of pieces—every single item can come together to create stunning and diverse looks! Just envision throwing on a fabulous trench over a cropped sweatshirt paired with a jumpsuit. Or picture a cozy puffer vest with a wide-leg denim. And of course, sneakers? They effortlessly elevate any outfit! The beauty of capsule wardrobes lies in the myriad of styles you can explore, so embrace the joy of creativity and make it your own!

Hope you thoroughly enjoyed this article—it was one of my favorites to write. I pour countless hours into diving deep into Amazon, handpicking my favorite items to feature, all for your convenience. So the next time you find yourself saying, “I have nothing to wear,” remember this blog is your treasure trove, brimming with inspiration to help you shine for any season, event, or occasion!

I appreciate your support, and if you want to be notified when I drop a new article, please subscribe. It means the world to me🩷

Xoxo

Jenn

Leave a comment

I created this space as a fashion destination for women who’ve lived a little, laughed a lot, and still love to show up every day with confidence and class.

Here, we embrace personal style over passing trends. Whether you’re rediscovering your fashion groove or simply want to elevate your everyday look, I’m here to help you feel inspired—not overwhelmed—by your closet.

Think of this blog as your go-to for outfit ideas, elevated basics, high-low styling tips, and a little real-life humor along the way. Because fabulous doesn’t fade—it just gets better with age.

Let’s dress like we mean it.