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May the Ray

A lifestyle blog for the dream chasers

Style · June 12, 2021

How to Slay Casual Streetwear with These 15 Outfit Ideas

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This post may contain affiliate links. Read my privacy policy for more.

This post is all about how to put together the best casual streetwear outfit ideas.

There have been so many styles and aesthetics that have come and gone over the years. But the one thing we can all focus on now is how our clothes make us feel. Some people want feel confident, or sexy or cute and modest. We’re a generation that is embracing it all and realizing we can wear whatever we want!

Feeling a little lost on the whole “streetwear” trend? No worries! Just think of your everyday closet favorites: comfy jeans, a classic tee, that trusty hoodie. Streetwear takes those basics and injects them with an extra dose of personality. It’s about turning the ordinary into the extraordinary, all you need are the clothes and the confidence to pull of this aesthetic.

What is Street Fashion Actually About?

Think oversized tees that drape like a boyfriend’s shirt, graphic band tees, and sneakers that add a pop of personality. Streetwear isn’t about following specific trends or wearing specific things, it’s about expressing yourself. And that is what makes it such a fun aesthetic to experiment with! Toss out the rulebook with this one and embrace clothes that are comfortable and confident.

Keep reading for 15 killer streetwear looks that’ll inspire you to create your own unique style statement. So, get ready to break the fashion mold and strut your stuff with confidence!


1. CROPPED PRINT TEE, JEANS AND DOCS

graphic shirt with jeans outfit
instagram: @nicolealyseee

There is nothing more classic than a black printed tee and some jeans! And doc martens always effortlessly give an outfit that extra cool factor!

2. PRINTED TEE, MINI SKIRT & BOOTS

mini skirt and graphic top outfit
instagram: @evthalia

This outfit is really bold if you don’t wear mini-skirts a lot but paired with the tee and boots, it makes for a really cute outfit! (The knotted t-shirt and boots are bringing cute-girl fashion to the street style party!)

3. FLANNEL BLOUSE, CROP TOP & DENIM SHORTS

instagram: @andyanglarill

I love flannel. Please tell me I’m not alone in this obsession! Honestly if you hate flannel, you’ve just never styled it right (jk!)…. An open flannel blouse is a street wear staple, and paired with this crop top and shorts (and the badass boots of course), its a simple and cute outfit!

4. ALL BLACK PRINTED TEE AND PANTS

baggy jeans and graphic shirt outfit
instagram: @marshdiadem

All black outfits are always guaranteed to make you look like a badass. This baggy tee and pants outfit is of course no exception!

5. BAGGY PRINT TSHIRT AND JEANS

oversized top and jeans outfit
instagram: @paulineantxo

I love how early 2000s fashion is making a slow comeback! Bring back the baggy jeans!

6. BLACK JEANS, CROP AND SANDALS

jeans and a crop top outfit
instagram: @josipellicano

These jeans are everything. Street style aesthetic doesn’t always have to be printed tees and tough girl boots!

7. BIKER SHORTS OUTFIT

biker shorts and a denim jacket outfit
instagram: @freyakillin

If you’re bold enough to wear biker shorts outside of the house (confidence at level 100) then this is such a trendy summer outfit.

8. LEATHER JACKET, JEANS AND BOOTS

girl wearing combat boots and a crop top outfit
instagram: @todecrespa

This is for sure an effortlessly chic and trendy outfit, the chunky boots and oversize jacket are just perfect!

9. LITTLE BLACK DRESS & OVERSIZED FLANNEL SHIRT

girl wearing a dress and plaid shirt
instagram: @paudictado

Yes little black dresses have a special place everywhere, even streetwear fashion!

10. OVERSIZE PRINT TEE & SHORTS

girl wearing black shorts and a black top
instagram: @cheyennetb_

Earlier I mentioned how trendy biker shorts can be. Lets scratch that, biker shorts are trendy, biker shorts need to be in…

11. TENNIS SKIRT OUTFIT

girl wearing sneakers, skirt and an oversized t-shirt
instagram: @yenlinhlee

Printed tee over a collared shirt?! It shouldn’t work… but it does. Pair that with the cute pleated mini-skirt and some Nikes and you’ve got a cute outfit!

12. TUCKED PRINT TEE AND JEANS

girl wearing jeans and a t-shirt
instagram: @clara.diefke

Anyone else obsessed with the checkered vans? Those babies are cool. And we love a wide leg jean here, so we’re living for this outfit (and by we I mean me (this is a one man show after all!))…

13. FLANNEL SHIRT AND SHORTS

girl wearing shorts and a crop top
instagram: @stefaniexlee

Like I said before, here at May the Ray, we love a good flannel shirt! They go with literally anything! Just look at this crop top and shorts outfit…

14. LACY CROP TOP AND JEANS

girl wearing red shoes, baggy jeans and a crop top
instagram: @eucarolsoaress

Street style can also be feminine as in a cute lacy top and not just baggy t-shirts! You can also add a little pop of color to your looks with a colorful pair of sneakers.

15. HOODIE + TENNIS SKIRT

girl wearing mini skirt and baggy t-shirt
instagram: @fiorella.del

Pleated mini skirts are the absolute cutest, they always take me back to my high school P.E. days of feeling preppy, sporty and cute!


Street fashion is such a versatile style of fashion. It’s a style that can honestly be anything you make it. That is why it has become such a popular fashion style… Did you love these streetwear style inspirations?

Posted By: ngozamay · In: Style

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About Me

May is a twenty-something year old lifestyle blogger who likes travel, food and spends inordinate amounts of time reading. Her life motto is "try everything at least once!" Read More…

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Hi there! I'm May and welcome to May the Ray, a young adult lifestyle blog where I share tips about lifestyle, food, fashion (+ so much more!), and where I try to inspire people to live life to the fullest!

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