Have you ever seen someone walking down the street and just thought: Wow, they look so cool? This list is basically the formula for that.
From casual weekends to more polished moments, I’ve got you covered with some of my absolute favorite street style inspiration.
1. Black Blazer and White T-Shirt
Is there anything more timeless than this combination? You really can’t go wrong here. A black blazer layered over a white t-shirt is the very definition of effortless style.
I love this look paired with some light-wash jeans and a black belt to keep things casual but still so put-together.
2. Puffer Jacket and Turtleneck Top
Some trends just prove they are here to stay, and this look is honestly such a wardrobe staple. A puffer jacket over a turtleneck top gives you a cozy and totally stylish silhouette.
Just add some wide-leg jeans and white sneakers to keep the whole vibe casual and ready for the street.
3. Charcoal Gray Oversized Blazer and Burgundy Leather Wide-Leg Pants
If you’re hoping for a look that will make people stop and stare, this bold combo is definitely for you.
I’m obsessed with how a charcoal gray oversized blazer looks paired with burgundy leather wide-leg pants for a seriously striking contrast. Adding sneakers keeps the whole outfit grounded in that street style zone.
4. Oversized Blazer and Matching Mini Skirt
Let’s just forget the rules for a second. This outfit is all the proof you need that mixing formal with casual can be done so effortlessly.
An oversized blazer with its matching mini skirt makes for such a cohesive look. Then, throw on some knee-high boots for a little bit of edge. A leather handbag is the perfect finishing touch for this street-chic ensemble.
5. Crewneck Sweatshirt and Biker Shorts
For those days when your schedule is totally packed but looking put-together is still a priority, this combo is what you should reach for.
A crewneck sweatshirt paired with some biker shorts hits that perfect sweet spot between athleisure and street chic. I’d add sneakers and black sunglasses to finish off this cool look.
6. Polo Shirt and Jeans
Some outfits just have that timeless appeal, and I have to say, this one is no exception. A polo shirt combined with jeans creates such a clean and classic vibe.
All you need to do is add a belt and some sneakers to round out this essential street style outfit.
7. Checked Long Coat
Who said you have to pick between being warm and looking stylish? This look delivers on both.
A checked long coat gives any outfit an instant touch of sophistication, while a pair of black ankle boots provides a sleek finish.
This combination is ideal for that transitional weather, letting you layer up or down whenever you need to.
8. Tank Top and Plaid Maxi Skirt
Dressing for comfort doesn’t have to mean giving up on style. A simple tank top styled with a plaid maxi skirt offers a really interesting blend of casual and dressy vibes.
You can top it all off with a leather jacket for an extra bit of street cred.
9. Dark Halter Crop Top
Loving the whole Y2K fashion trend but want to give it your own spin? This outfit totally does that.
A dark halter crop top paired with dark wash wide-leg jeans results in a sleek silhouette. The platform sandals add some height and a little retro flair to this street-ready look.
10. Button-Front Plaid Jacket and Wide-Brim Fedora Hat
With a couple of simple swaps, you can elevate a basic outfit into a full street style statement.
I love how a button-front plaid jacket paired with a wide-brim fedora hat adds instant personality. Pleated wide-leg pants and some ballet flats keep this look grounded but still so fashionable.
11. Brown Leather Trench Coat
There is really nothing quite like a well-styled trench coat outfit. A brown leather trench coat brings a luxe touch to some light-wash denim jeans.
I think a pair of black pointed-toe heels really elevates the look, making it perfect for a night out or a fashion-forward day exploring the city.
12. Tank Top and Checked Wide-Leg Pants
For anyone who appreciates being comfortable but with a modern twist, this outfit is a total home run.
Pair a simple tank top with some checked wide-leg pants for a look that feels both relaxed and totally chic.
The unexpected choice of Crocs adds such a playful touch, which proves that street style is all about showing your personality.
13. Beige Oversized Blazer and Cream Striped Turtleneck Sweater
If you want a look that feels both classic and fresh at the same time, you should try this combination.
A beige oversized blazer paired with a cream striped turtleneck sweater creates a really sophisticated base. Black wide-leg trousers and white sneakers bring in some contrast, and a black baseball cap keeps it all casual.
14. Dark Bomber Jacket and White Hoodie
Want to know the secret to getting street style right? It really comes down to the layering.
A dark bomber jacket over a white hoodie creates that classic street vibe. Adding some black wide-leg pants and chunky loafers gives it an edgy touch, which makes this outfit work for a ton of different urban settings.
15. Cropped Cardigan and Crew Neck T-Shirt
For people who value comfort but still want a trendy twist, this look is such a great find. A cropped cardigan layered over a crew neck t-shirt feels like a fresh take on layering.
Just finish it off with some wide-leg jeans and black loafers for an effortlessly cool street style moment.
16. Light Puffer Jacket and White Wide-Leg Pants
Why go for something ordinary when you can make a real statement? A light puffer jacket styled with white wide-leg pants creates a fresh, monochromatic outfit.
A brown belt adds a little definition, and white sneakers keep the entire look grounded in that street style aesthetic.
17. Knit Sweater and Collared Shirt
It’s honestly amazing what just a couple of key pieces can do to completely transform your style. Layering a knit sweater over a collared shirt gives off a preppy-meets-street kind of energy.
I love that dark wide-leg jeans and loafers ground the look, making it a perfect go-to for casual Fridays or brunch on the weekend.
18. Striped Turtleneck Sweater and Silk Maxi Skirt
This look feels inspired by high fashion but has a street twist, which is such a fresh take on layering. A striped turtleneck sweater tucked into a silk maxi skirt is a totally unexpected pairing that just works.
Two-tone flats and some black sunglasses are the finishing touches for this eclectic street style outfit.
19. Plaid Cropped Jacket and White Wide-Leg Jeans
Let’s be real—the timeless appeal of plaid and denim just can’t be beat. A plaid cropped jacket worn with white wide-leg jeans creates a fresh and modern silhouette.
I am loving how the red pointed-toe slingback heels add a pop of color, while a white headscarf brings in a touch of vintage charm to this street-savvy outfit.
20. Black Puffer Jacket and Ombre Scarf
If effortless style is the goal, then I think this outfit is your answer. A black puffer jacket paired with an ombre scarf adds so much visual interest to the wide-leg gray jeans.
The look is completed with black chunky boots, which are perfect for walking around city streets in style.
21. Black Oversized Blazer and White Crew Neck T-Shirt
When your plans require both comfort and style, this outfit has you covered. A black oversized blazer thrown over a white crew neck t-shirt offers a perfect blend of casual and polished vibes.
A black belt and some knee-high boots add structure to this versatile street look.
22. Button-Up Jacket and Matching Wide-Leg Trousers
With a little bit of coordination and a whole lot of personality, this outfit is one you have to try.
A button-up jacket with matching wide-leg trousers gives you such a cohesive look. Layer a white button-down shirt underneath and then slip on some brown clogs for a fun, unexpected twist.
23. Oversized Button-Up Shirt and Tank Top
One of the simplest ways to make a statement is just by playing with proportions. An oversized button-up shirt layered on top of a tank top creates a relaxed yet totally put-together outfit.
Keeping it in the street style zone, just add cargo jeans and sneakers.
24. Long Coat and Turtleneck Sweater
This outfit is a total winner for those days you want to look stylish without putting in a ton of effort.
A long coat layered over a turtleneck sweater creates a really sleek silhouette. The wide-leg trousers and white sneakers keep the whole look feeling contemporary and street-appropriate.
25. Faux Fur Long Coat and Knit Sweater
Looking to elevate your everyday style? You can start with this cozy yet chic combination. A faux fur long coat layered over a knit sweater adds so much texture and warmth.
I love that the wide-leg jeans and leopard print slip-on shoes bring a dose of fun into this street-ready outfit.