Ever wonder why certain guys always look effortlessly cool walking down the street? They’re stealing notes from celebrity off-duty moments. From A$AP Rocky’s layered hoodies to Harry Styles’ vintage band tees, find 25+ celebrity-approved street style combinations now!
These laid-back yet chic looks featuring oversized fits, statement sneakers, and unexpected accessories prove that the best street style inspiration comes from simple and common pieces when you style them rightly!
1. T-shirt and Dungarees
Blend comfort with cool in this sleek combo that you can style alongside dainty pendants, classic sneakers, and a dark snapback!
2. Oversized Graphic Sweatshirt and Slim-Fit Jeans
Pair your casual jeans with a statement graphic sweatshirt, neck chains, dark sneakers, and wayfarers in this cool hangout fit!
3. Sweatshirt and Skinny Jeans
Try this smart casual street look in dark tones with bold sneakers and dainty chain jewelry for that effortless suave!
4. Striped T-shirt and Chinos
Add a retro touch to your modern street style look with this suspenders and chinos combination! Top the look off in dark sunglasses and chunky sneakers!
5. Hoodie, Puffer Jacket, and Baggy Pants
Rock this relaxed combo for your wintertime outings with matching beanies and thick rimmed sunglasses for a playful touch!
6. Turtleneck Sweater, Ripped Jeans, and Sherpa Coat
Opt for this classy street look for your winter strolls with matching beanies, high ankle sneakers, and Cuban neck chains for a cool front!
7. T-shirt and Joggers
A sleek day-to-night streetwear combo to try on, style this one in high-top sneakers and denim jackets for the perfect laid-back appeal!
8. Vest Top and Shorts
Make your beach or coast visits look extra cool in this sporty combo that you can style in ankle sneakers, dark sunglasses, and layered pendants in silver!
9. T-shirt, Overcoat, and Slim-Fit Jeans
Bring in a classy twist into your hangout looks with this street fit, dark wayfarers, and contrast beanies to style it in! Add in white sneakers for a casual streak!
10. Hoodie and Cargo Pants
Resonate spontaneous energy with this night out look that you can pull off in contrast hues, high top sneakers, and a bold baseball cap!
11. Oversized T-shirt, Solid Jacket, and Regular Fit Jeans
Look undeniably chic in this cool combo and white sneakers! Opt for light-washed jeans with dark wayfarers completing the fit!
12. T-shirt, Baseball Shirt, and Shorts
Try this sporty street look for your summertime hangouts or matches in bold hues with chunky sneakers and a classic cap in dark hues!
13. Hoodie, Flannel Shirt, and Joggers
Make your street look scream effortlessly trendy with this casual combo, platform high top sneakers, and dark beanies!
14. Oversized T-shirt and Shorts
A casual streetwear look to don as you’re out running errands, complete this one in baseball caps, ankle socks, and casual sneakers for a sporty appeal!
15. Hoodie, Varsity Jacket, and Joggers
A sporty athleisure look for winter hangouts! Style this one in contrasting hues like white and black or cream and brown, along with beanies, dainty pendants, and chunky sneakers.
16. T-shirt, Cargo Pants, and Bomber Jacket
Upscale your street looks to statement edgy fits with this combo, leather belts, Cuban chains, and chunky boots in dark hues!
17. Oversized Graphic T-shirt and Tapered Baggy Pants
A funky streetwear fit to rock in bold hues, give this one a playful appeal with vibrant bucket hats, pattern socks, and chunky sneakers!
18. Solid Shirt and Camouflage Baggy Pants
Rock this bold streetwear combo minimally with dark beanies, cord bracelets, and combat boots in black!
19. Sweatshirt and Jogger Pants
Channel a sophisticated grunge energy into your summertime street looks with this monochrome combo alongside ripped arm warmers and chunky shoes!
20. T-shirt, Zipper Hoodie, and Cargo Pants
Channel the perfect balance between classy and urban with this sleek streetwear pick, Cuban chains, funky print sneakers, and an optional beanie!
21. T-shirt, Cargo Pants, and Varsity Jacket
Radiate a laid-back urban energy with this street pick that you can style in platform boots and a Cuban chain!
22. Denim Jacket, Baggy Jeans, and T-shirt
Strike the perfect 2000s throwback street fit in this stellar combo, chain necklaces and chunky sneakers! Try low-waist jeans for retro appeal!
23. Cropped T-shirt and Shorts
Bring in a youthful glam into your casual streetwear looks in this pattern combo, ankle socks, casual sneakers, and dainty charm jewelry!
24. T-shirt, Varsity Bomber Jacket, and Cargo Joggers
Pull off this sporty streetwear combo in neutral hues with ankle sneakers and a dainty pendant in silver for your casual outings!
25. T-shirt, Jacket, and Slim Fit Jeans
Functional and trendy, this one’s your go-to street look to maintain a laid-back appeal naturally! Add in dark beanies and casual sneakers to amp up the vibe!
26. T-shirt, Baggy jeans, and Leather Jacket
Channel the cool ’80s street style air with this solid combo, casual sneakers, and dainty chain jewelry!
