15+ Best Vintage Streetwear Outfits To Rep In 2022


HF Lanzer

Streetwear outfit

Did you say Streetwear + Vintage + Outfit in the same breath, there? Well, you’re our kinda person, as we think this fashion combo is an out and out winner and now we’ve caught your eye, read on to see us putting our money where our mouth is, as we present you with a selection of exciting, sustainable and affordable ideas to make a splash when we now emerge from the heatwave summer of 2022.

OK, so the joy of choosing a vintage streetwear outfit is that you do not need to start from scratch and begin with brand new off the peg garms, but it is easy to mix what you have, match what you long ago discarded and source a few pre-loved bespoke numbers to swiftly put together a winning and unique ensemble. Not a new outfit, but new to you and kind on the planet.

What is Vintage Streetwear?

Vintage streetwear is an area of fashion which encompasses all styles of casual wear worn by people to reflect the popular culture of their day, be it from the 80s, 90s or 00s. It is a broad term, which includes fads and movements throughout the decades, including sports, K-pop, grunge, hip-hop, skater, surf and rap. You name it, chances are there is a streetwear ‘uniform’ accompanying it. And a host of these clothes is still available to snap up today.

Of course, we always define the term vintage as referring to clothing stock manufactured at least 20+ years ago, so we are not looking at the new items being promoted today by influencers and the big brands to replicate the vintage decades. No, there is absolutely no need to look for new anything in this domain.

The purpose of this week’s blog is simply to help you find inspiration for vintage streetwear outfits, which you can then adapt to suit your personality … or copy as best you can! We know, inspo is not always knocking at the door with all the other demands on our lives, so this blog is for you! We’d also recommend browsing on the gram or the web or taking a swerve now to look at our blog How To Develop Your Own Unique Fashion Style about how to find inspo for a new style you’re developing.

We’ve split our inspo into Female and Male sections, but of course, there is no need to be gender-led with this, as to which one you choose. Mix and match and refuse to be pigeonholed is our recommendation. Just be true to yourself.

Mens Streetwear Style

8 Of Our Favourite FEMALE Streetwear Outfits

1. Racing Jackets

Women Streetwear outfit

Vintage racing jackets have hit the mainstream of late and for good reason. Although they might put you back a pretty penny (£100+), they are a staple of any streetwear outfit. This timeless workhorse will continue to earn its keep long past its price tag, so it is well worth looking through the vintage sites to see if you can track one down at a cost within your budget. Then just add jeans! 


2. Cargos & Baggy T-Shirt

Women Streetwear outfit

You can’t go wrong with a pair of vintage baggy cargos and a 90s oversized tee … an outfit match made in heaven.


3. Vintage Sweatshirt & Anything

Women Streetwear outfit

You can chuck a vintage vintage sweatshirt on alongside almost any outfit and it’ll look good. Guaranteed! Pair your vintage sweatshirt with baggy or slimmer jeans or shorts, as a clean way to achieve that streetwear style.


4. Varsity Jackets

Women Streetwear outfit

If a racing jacket comes in over your budget, then look out for its cousin, the vintage varsity jacket, as this mainstay of the fashion scene throughout the decades, will certainly pack a punch and do the trick to finish off your vintage outfit. Just add bottoms of your choosing. 


5. Baby Tees & Baggy Trousers

Women Streetwear outfitYou won’t get much more 90s than the iconic baby tee – graphic, pastel, patterned, tie-dye – and pairing one of these with some baggy bottoms to create that streetwear contrast is an out and out winner.


6. Gilet & Baggy Sweatshirt

Women Streetwear outfit

Moving on slightly to the winter, the ideal candidate here has to be a nicely fitting gilet accompanied with an oversized sweatshirt to hit that 90s streetwear aesthetic bang on. Pairing with really any bottoms you want, as long as they’re not too skinny, and wham bang, your outfit is ready! Just remember, a vintage streetwear outfit is all about keeping it it casual, loose and oversized.


7. Bike Shorts & Baggy Sweatshirt

Women Streetwear outfit

Sporting a classic vintage sweat paired with a contrasting tight-fitting pair of bike shorts and a pair of chunky shoes is perfecto!


8. Vintage Colourblock Windbreaker Jacket

Women Streetwear outfit

Finding a colourful 90s windbreaker jacket and pairing it with pretty much anything, will certainly bring out that streetwear aesthetic in you. Prime options for pairing include a classic pair of baggy jeans or bicycle shorts. Try out some options yourself!

8 Of Our Favourite MALE Streetwear Outfits

1. Collared Shirt Under Sweatshirt

Mens Streetwear Style

Yep, this is as streetwear simple as it sounds! Chucking a collared shirt under a 90s vintage sweat and pairing them with straight legged jeans is as good as it gets in our book … and very little effort required!


2. Hoodie/Sweatshirt & Baggy Jeans

Mens Streetwear Style

This is classic vintage streetwear outfit style. Baggy on baggy is what we’re after, and if you pair that with a cheeky cap and some cool accessories, you’ll be laughing. Oh, before we forget on this one, don’t forget the all important touch of a lil of the tee peeping out cheekily below your sweat/hood.


3. Oversized Tee & Baggy Jeans

Mens Streetwear Style

The same here, as just above, but this time with short length sleeves, perfect for a hotter day or a party vibe …  we actually have a full guide here on how to style an oversized tee, if you are in any doubt.


4. Oversized shirts

Mens Streetwear Style

Now, if you’re feeling a little classier and not sure about all the oversized this and that, then don’t give up on the idea of a vintage streetwear outfit being for you! Streetwear still has the perfect and simple option you’ll love, so give it a go and try an oversized shirt matched with some baggy jeans and you’re on your way to the ball!


5. Vintage Colourblock Windbreaker Jackets

Mens Streetwear Style

Copping a colourblock 90s windbreaker jacket provides you with the essential component of any wardrobe, as this piece can be effectively matched with any of the outfits above to complete your vintage outfit  … defo worth a cop, click, keep moment!


6. Sweatervest + Tee

Mens Streetwear Style

If you saved any of your cricket vests with their old school tank-top style, find them asap! This style of a sweatervest, worn with a clean white tee and some straight jeans, is a streetwear dream.


7. Heavy Top Half

Mens Streetwear Style

Repping an oversized sweat WITH an even more oversized jacket and a pair of your fav shorts can give instant streetwear vibes: see for yourself and take some inspo below.


8. Everything Heavy

Mens Streetwear Style

Now, with this vintage streetwear outfit, we’ve got winter in our sights. These are the months when you might just wanna little added practicality to your vintage streetwear outfit  … and now’s your perfect opportunity to rep the whole fit and stay warm, so yes, we really are talking the oversized tee, the oversized hoodie, the fitting puffer jacket and the baggy jeans here. Outfit complete …


As we draw to a close of our look at vintage streetwear outfits, it really is down to you now as you consider what you prefer as your unique take on a streetwear vibe. But continue to pick and choose, match, adapt and discover, so whichever outfit you do put together over the coming months of 2022, you keep it sustainable, keep it fresh and above all keep it YOU.

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