How To Wear Vintage Streetwear In 2023


HF Lanzer

 vintage streetwear clothing being worn

Two factors to get to grips with here. Firstly, an understanding of the term ‘vintage’ as far as clothing is concerned (well, that’s sorted, as we covered this in What is Vintage Clothing?) and secondly, a grasp on the ubiquitous fashion style bandied about and known as ‘streetwear’.

So, combining the two, you can see that vintage streetwear lies within the realm of all the casual fashion trends repped back through the vintage years, be it from the 70s, 80s, 90s or 00s. Streetwear is a broad term, we grant you, as it includes youth fads and movements favoured throughout these decades, such as punk, new wave, hip-hop, grunge, heavy metal, skater, surf, rap, workwear … you name the fashion, chances are there was a streetwear ‘uniform’ accompanying it. And the best thing about all this, is that there is now a host of these era clothes still in circulation and sitting ready for streetwear fans to snap up and carry off themselves.

Of course, we always define the term vintage as referring to clothing manufactured at least 20 years ago, so we are not looking here at the new retro styled items being produced and promoted today by influencers, big name celebrities, media icons and the heavily-marketed brands which love to replicate vintage streetwear in their latest collections.

Despite the fact that there are still authentic versions around. No, there is absolutely no need to look for new anything in this domain. It’s all out there already and the old streetwear really is the gold streetwear!

Three Key Elements Of Vintage Streetwear

  1. The brands
  2. The colours
  3. The fits

The brands

You shouldn’t be looking for minimalist clothing with subtle and modest logos if you’re wanting to rep a streetwear vibe from the 90s and 00s, which was the time when the big, brassy brand logo was visible for all to see. Together with bold prints and graphics, the streetwear aesthetic really was eye-catching, especially in the hands of our fav 90s brands, such as Tommy HilfigerRalph LaurenNike and Adidas, to name but a few.

vintage branded sweatshirts being worn

The colours

90s and 00s garments often had lots of colours going for them, so check out vintage shell suits bold graphic sweatshirts and wacky fleeces from those eras to give yourself an idea of what to aim for in all things vintage urban. Neutrals can always play a role in any ensemble, simply by their non-controversial nature, but grey and black are a kinda no-no for vintage streetwear, so incorporate them with care!

colourful vintage clothing being worn

The fits

A streetwear fit has to be generous, cosy, comfy and above all … loose fitting. End of! As far as we’re concerned, go big, go baggy, but always keep an eye on the end result and seek to maintain a cool and relaxed form to your baggy vintage streetwear style. Looking for inspo, check out our blog on Oversized Outfits to check you’re on the right track.

oversized vintage clothing being worn

Vital Vintage Streetwear Attire

The T-Shirts

If you’re just starting to add vintage streetwear to your wardrobe, we’d strongly recommend the urban tee as your first port of call – we believe this short-sleeved beauty is the most fun,  versatile and affordable item you can incorporate into your outfit. In fact, we rate the glorious vintage tee so highly, we even wrote a handy blog on the joys of this streetwear classic, How To Wear Oversized T Shirts. When dabbling with T Shirt style, set off to look for designs displaying areas of personal interest, such as movies, cars, sports, bands, games – 90s graphic tees will not let you down.

vintage t-shirts clothing being worn

The Pants

Next up, is the need to source a pair of vintage jeans or cargos, ideally going for that faded, worn-in look. Failing that, you can try to ‘vintagify’ an existing pair yourself, by putting it in every wash, lightly bleaching or spotting with bleach, adding wear and tear with the help of a sharp object or pumice stone/sandpaper to provide DIY ageing support. Or, you can play a longer game by wearing the bottoms out yourself, while also unpicking the hem in places and leaving to fray slightly. The fit can be pretty much anything, other than skinny, so experiment with straight, slim or baggy. If you’re opting for cargos, bear in mind that a baggy pair of these really can provide the icing on the cake of any streetwear outfit.

vintage pants being worn

The Tops

Your next vital vintage vehicle is the all conquering hoodie, zip-through or sweatshirt – fortunately for everyone, these items count among the most popular sold online, so it really is buyer’s choice. Check out Best Online Vintage Stores 2022 if you’re unsure where to turn first, given the huge number of retailers out there. A smart way to target your search is to go for a brand you particularly like in banging 90s colours (not black or grey, remember!) with a cool logo and a looser than average fit – then sit back and enjoy watching your vintage streetwear collection building.

vintage sweatshirts being worn

The Footwear

As for footwear, we’d recommend any shoe or trainer that was popular back in the 90s and 00s or one in a similar style, so we’re thinking here Converse 70s, Jordan dunks/1s and the classic Air Force 1s. Nike and Adidas were the biggest brands on the market, but other names such as Fila and Reebok, had some killer shoes to look out for. Browsing the vintage marketplaces or visiting charity shops could be your best bet to find the perfect pair in your size, as they really can be rare.

vintage sneakers being worn

The Accessories

Once you’ve got the basics sorted, it’s time to venture forth and discover some more adventurous pieces, including caps, bags, belts and stand-out pieces that would work well with the vintage streetwear clothes you have selected to feature in your outfits.

vintage accessories being worn

Finding Your Vintage Streetwear Look

We’ve given you an insight on what vintage streetwear is all about and what you should be looking for ... so now it’s time to get hands-on with the assistance of decent inspo to guide you further. Taking ideas from celeb feeds and reels on social media platforms, blogs, videos, interviews and posts are all great ways to start embracing vintage streetwear as your look – the great thing with vintage is the fact that it provides an astoundingly varied and rich collection of clothing items. Due to this factor, you are perfectly poised to gain ideas from someone and then set off solo to find a piece that is vaguely similar while still remaining so unique that no one else will look the same as you. So, just keep those eyes peeled and ensure you always aim to make your streetwear look your own, How To Have A Unique Fashion Style.

vintage clothing being worn

Vintage Streetwear Outfit Ideas

You can see a selection of our favourite vintage streetwear styles on our blog 15+ Best Vintage Streetwear Outfit Ideas For You To Adopt, which covers all the different styles and general inspo for you to get some ideas for your own wardobe!

Where To Source Vintage Streetwear

The surge in online vintage clothing websites, as witnessed over the past few years, coupled with the ever-trusty physical stalwarts selling second-hand winter coatssweatshirts and track tops, to name but a few, has led to vintage clothing becoming a veritable obsession. And a highly affordable one to boot! Check out our blogs Where to Buy Affordable Vintage Clothing, Where to Buy Baggy Clothes and Where To Find And Style Vintage Aesthetic Clothes for some more quick ideas on how to shop streetwear-aligned vintage clothing. Or take a look at these handy suggestions of places to turn to:

1. Online Vintage Stores

The best place would be online vintage stores who specialise especially in vintage streetwear and handpick all of their items. Vintage streetwear is a niche in vintage and is tough to find by yourself in charity shops and carboot sales ect. Some of the best online retailers would be:

2. Depop/Vinted

Depop and Vinted are two go-to apps to start your hunt for vintage streetwear. Here, individuals sell their used clothes, and a lot of the time, you can find vintage streetwear which is way cheaper than that offered at a vintage store. Don’t be too timid to message the seller and offer a lower price, if you come across an amazing streetwear jacket or hoodie.3.

3. eBay

By searching for ‘vintage clothing’ on eBay, you will automatically find a wide variety of awesome vintage clothes being sold which all come under the streetwear umbrella. Filter specifically for ‘streetwear’ or other relevant terms,  such as ‘baggy’, ‘urban’ or ‘Y2K’ and see what you can track down to Buy Now or join in the buzz of an Auction bid.  


Vintage + Streetwear = Our Kinda Outfit! Streetwear is a way of dressing which is so non-prescriptive in its approach, that everyone can successfully rep it, while still retaining their very ownsome unique dress style. Given the huge selection of vintage clothing from the past 20+ years  available today, streetwear fashion is also a reasonably priced and highly sustainable choice among the ‘what to wear and show you care’ clothing styles repped today!

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