90s Oversized Shirts: Style Guide & Look-book!

90s oversized shirts header

90s¬†oversized shirts have made a comeback and are currently grabbing attention everywhere! This trend is all about going big or going home with shirts that are several sizes larger than what you would normally wear. The look has been spotted on the runway, in street fashion, and even among celebrities. Let’s start you off with a colour palette and mood-board inspired by this re-emerging fashion phenomenon:

A moodboard and colour palette showing off 90s oversized shirts

90s Oversized shirts offer¬†versatility¬†‚Äď they can be paired with leggings, shorts, jeans or even worn as a dress. They also make for comfortable and breezy summer wear. In addition, the sheer volume of fabric gives an instant laid-back vibe that many find appealing.

What sets the 90s oversized fashion apart is its boxy shape and casual appeal, but modern versions can feature unique prints or bold colors to add personality. Think bright floral patterns or graphic designs.

If you’re looking to¬†rock this trend, then you’ll enjoy our comprehensive style guide that will give you ideas & looks to inspire you! We have a total of ten different 90s oversized outfits for you to explore and we hope you find them both inspirational and educational when it comes to pulling off 90s oversized shirts!

Table of Contents

How to Style 90s Oversized Shirts

To style oversized shirts from the 90s, you need to get creative with how you wear them. Bring a fresh twist to your wardrobe with tucked in, belted and layered styling options that will give you a classic 90s oversized outfit look. Each of these solutions offers a unique way to make a statement while still keeping up with the vintage trend.

Get Inspired with our Outfit suggestions below and read on to see various celebs rocking the looks and ideas to how to make the look your own!

five different 90s oversized shirt outfits with a casual vibe
five different 90s oversized shirt outfits with a streetwear vibe

The Slip Dress with Tied 90s Shirt Look

One of the ways to add layers and shape to your overall look is to tie up your 90s Oversized top at the waist.  This look can transform a standard slip dress and tee shirt combo into a more iconic and fashionable outfit.

A 90s oversized shirt outfit with a slip dress and t-shirt plus choker

To accessorize, find a matching choker to complement your slip dress and of course keep the underlying t-shirt in a neutral black or white color that doesn’t cling to your body but also keeps your shape. If Drew Barrymore used to rock it, you can too!

Adding a watch with a similar color palette to your choker can give you the finishing touch for a perfect retro look!

The 90s Oversized Shirt, Shorts & Summer Look

To create a unique and edgy look with oversized 90s shirts in the summer, use multiple layers to make a bold statement. By incorporating this style into your wardrobe, you’ll be able to play with different looks while staying true to the loose-fitting trend of the era. This type of look comes to you straight from the catwalks!

A 90s oversized shirt outfit with denim shorts and a white crop top plus sunglasses

In the style above we’ve paired the oversized shirt with a basic crop top, tight jean shorts and matching¬†90s sunglasses. This lets you¬†layer¬†up and down through the course of the day and keeps you look stylish throughout!

We love this look because you can pair it with some iconic 90s sneakers or keep it simple with flip-flops or sandals!

The Dungarees & 90s Flannel Look

Is there anything cooler and more retro than 90s Dungarees? For this amazing look, embrace your inner Salt-N-Pepa. You can wear the dungarees done up with either one or both straps and let’s be honest… the baggier the better!

If you’re in sunnier climates then you may consider swapping out your dungarees for some¬†90s overall shorts¬†instead, the aesthetic will be largely similar and you can still style it with the outfit below:

A 90s oversized shirt outfit with dungarees and a white vest

For the under layer we like to keep it simple with a sleevless¬†90s vest¬†or crop top and wrap the 90s oversized shirt around the waist. You can also wear it over the top of the outfit like we’ve shown in both our inspirational pictures above!

No accessories strictly needed here but if you’re feeling really nostalgic, you can match the whole outfit with a¬†90s hat, it’ll make you even more fashionable and keep your head out the sun, win-win!

The Classy Dukes of Hazzard Look

The knotted 90s oversized shirt was made iconic by classic 90s show the Dukes of Hazzard but we’ve elevated¬†the Daisy Duke look¬†by replacing the show’s tight denim shorts with a¬†90s strappy mini dress¬†and an under layer of a white t-shirt:

A 90s oversized shirt outfit with a slip dress and t-shirt over the top

Accessorizing this look is elegant and simple to do; find a matching (or somewhat matching) scrunchy for your hair and you’ve nailed it! There really is nothing else required for this look although a cheeky pair of small¬†90s hoop earrings¬†would not look out of place!

Tucked In & Belted Oversized 90s Shirts

A 90s tucked in shirt can transform your look. I mean if Julia Roberts and the cast of Friends can pull it off, why can’t you! We recommend folding the shirt neatly, making sure it hugs your body to avoid bulkiness so that you have a polished finish. Baggy fitting or wide-legged jeans / shorts can balance out the leanness of the shirt.

A 90s oversized shirt outfit with baggy jeans and a belt

You can thinly belt your oversized 90s shirt to accentuate your curves, or to hide the fact that you’ve been living on pizza and beer for the past month! We’d recommend accessorizing further with a claw hair clip to properly complete your 90s look!

The Urban & Oversized Look

Seen on Catwalks any on various celebrities too, this unstoppable look catches attention with baggy joggers, a plain crop top and a statement 90s oversize shirt. This outfit is designed to really accentuate the 90s shirt and so it merits finding a special one that you absolutely love! 

An oversized 90s shirt with streetwear joggers and a bucket hat

If you’re cool enough to attempt the Rhianna look (top right) then you can whip out your best sunglasses, tuck in your shirt and throw on your best silver necklace.

Our preference is to adorn a Bucket Hat colour-matched to the joggers and letting the shirt hang untucked and easy breezy!

Daisy Duke meets the Fresh Prince

We owe this look entirely to the character Ashley Banks from the Fresh Prince of Bel Air! It’s an understated and easy way to introduce a 90s oversized shirt into your rotation of looks!¬†

We suggest taking your 90s shirt and making use of the tie-up belly style and then pairing a simple pair of straight leg (or even tight) 90s jeans.

A 90s oversized shirt tied at the waist with jeans and a vest

An under layer of a white vest will help to accentuate the shirt itself and if you throw in a matching scrunchie then you’ve completed the look! We’ve gone for earthy colors in this example but a style like this affords you a broad set of choices!¬†

Clueless Inspired 90s Oversize Shirts

Can we start anywhere else with this look than to possibly the best¬†90s movie¬†ever: Clueless! We’ve modernised the look of course, we couldn’t have a host of potential outfits without embracing the casual fitness look that we all love to rock on a daily basis!

Our under layer of lycra shorts and strappy croppy top paired with a simple white tee shirt give you both comfort and style but the it’s the wrapped 90s oversize shirt that really brings the outfit to life! With a style like this, you really want bold colours and what better inspiration than Alicia Silverstone?

A Jennifer Anniston 90s oversized shirt look

This look is completed by a simple black cap, thank you Jennifer Anniston for bring this look to life for us! The whole outfit ends up giving us the perfect combination of the greatest movie and the best tv show to grace our screens in the 90s!

Double Denim with 90s Oversize Shirts

Does Double Denim even need an introduction? Such was its iconic status in the 90s that you couldn’t leave the house without seeing someone rocking it!

We’ve kept this look as true to its roots as we possibly could with a scrunched/tied white tee and then matching jeans and denim overshirt.

A double denim 90s oversized shirt outfit

One of the great things about classic looks like this is adding a modern touch with accessories. The bum bag used to be much ridiculed but now its re-emergence makes this pairing a great fit, go for a plain black leather one and a necklace too.

There you have it, a throwback to double denim in a trendy new way!

90s Oversize Shirts as a Dress

Dig out the biggest, most oversize shirt you can for this bad boy. You want it at least thigh level or below, that will give you the kind of look we’re going for here. For modesty’s sake, we’d recommend some Lycra shorts underneath, we don’t want any Mairlyn Monroes here!

90s Oversized shirts styling guide with an oversized shirt as a dress

This look is completed by the addition of some simple hair clips, a black belt to thin the waist and pulled up white sports socks (we love Nike or Adidas as a pairing here). A pair of box fresh white trainers would really finish this look perfectly.

General Styling tips for 90s Oversize Shirts

We hope you enjoyed our suggested outfits, we think there’s plenty of inspiration there but if you want a few more generalised tips about styling then look no further!

90s Oversized Shirts with Belts

As we’ve seen in our outfits, one way to enhance your look is by adding a belt. Secured around your waist you can get a more tailored and flattering shape.

A wide or chunky belt can create a statement look whereas a simple thin one can add elegance. You can wear it slightly higher if you want to accentuate your waistline or lower if you prefer a relaxed style. 

The belt also gives you the chance to style your Shirt in a number of ways. Tuck in the front or leave it out for an effortless look.

Layering Oversized 90s Shirts

Almost all of our looks utilized layering to create a unique and edgy look with our oversized 90s shirts. Primarily we encourage you to use under layers like plain white t-shirts, crop tops or vests so that your shirt was the main start of your look.

Accessorizing with 90s Oversized Shirts

To accessorize your 90s oversized shirts, use jewelry, hair clips, under-layers and sunglasses to freshen up your looks! These upcoming sub-sections will give you the edge to complete that head-turning 90s look. 

By adding the right jewelry, you can elevate your outfit and make it more sophisticated. Everything from chokers, to necklaces, hoop earrings to bracelets, there’s an endless supply of jewelry opportunities.

The right pair of sunglasses can give you confidence and take a mundane outfit into a totally cool and trendy one. 


For those looking to enhance their 90s oversized shirts, consider adding complementary accessories to complete the desired look.

  • Statement Earrings: Elevate your style with bold earrings that match your outfit.
  • Cuff Bracelets: Enhance your wrist with a simple yet elegant touch.
  • Layered Necklaces: Create depth and interest by layering necklaces of varying lengths and styles.

To truly stand out, try adding vintage or unique pieces to your jewelry collection, such as retro brooches or heirloom rings.

Fun fact: According to Harper’s Bazaar, layered necklaces were one of the top accessory trends in 2021.

When it comes to accessorizing with oversized 90s shirts, don’t forget the sunglasses – they’re the perfect way to hide your eye roll when someone asks if you’re wearing a muumuu.


The 90s Oversized shirt trend is not complete without the right eyewear. We recommend playing around with any of these!

  • Oversized sunglasses¬†are a classic accessory for the 90s look.
  • Aviator frames¬†add a touch of edge to the outfit.
  • Colored lenses¬†create a fun and playful vibe.
  • Cat-eye frames¬†bring out femininity in the ensemble.
  • Round shades¬†create an effortlessly cool appearance.

For those seeking a bold statement, opt for angular or geometric frames that offer a unique twist on traditional styles.

To complete the overall look, pair¬†round frames with casual outfits¬†and¬†colored lenses with monochromatic looks.¬†Aviator frames work best with denim jackets¬†while¬†cat-eye glasses¬†complement flowy dresses. When experimenting with eyewear, it’s important to keep personal style in mind to elevate rather than detract from one’s aesthetic.

Celebrities and Fashion Icons Wearing 90s Oversized Shirts

Celebrities and well-known fashion icons are elevating their style game by sporting 90s oversized shirts. Here are five examples of famous personalities who have been caught on camera wearing these iconic shirts:

  • Beyonc√©¬†– The queen of pop music was once spotted flaunting a pinstripe oversized shirt during her street style appearance.
  • Justin Bieber¬†– He elevated his casual look with a long blue oversized shirt while grabbing lunch in Los Angeles.
  • Megan Fox¬†– She paired her distressed denim shorts with an orange oversized shirt during the production of one of her movies.
  • Kendall Jenner¬†– She was seen stepping out in an all-white ensemble that included an oversized white shirt, stole the spotlight instantly.
  • Dua Lipa¬†– The British singer showed off her fun personality by donning an oversized Garfield printed shirt at one of her concerts.
Of course, this list doesn’t even cover the OG 90s celebs that totally made this a fashion trend in the first place:
celebrities wearing 90s oversized shirts

These iconic figures prove that wearing oversized shirts is back in style. Not only does it add a glamorous edge to your casual wardrobe, but it also offers comfort and a carefree style statement.

Taking inspiration from these celebrities, why not update your wardrobe with this laid-back trend? Elevate every outfit and go big or go home! Why settle for a regular-sized shirt when you can look like you raided your dad’s closet with these authentic 90s oversized shirts?

Dos and Don'ts of Wearing 90s Oversized Shirts

To ace the 90s oversized shirts trend, you need to know the dos and don’ts of styling them. In order to rock this look with confidence, start by experimenting with different fabrics. But remember to balance out the proportions for a flattering silhouette. Accessorizing is a must, but it’s important not to overdo it.

Do Experiment classic 90s Patterns

These classic patterns can add a laid-back yet sophisticated vibe to your outfit. Try a cotton oversized shirt in different colours depending on your intended style.

An oversized shirt in bold colors like red or pink can easily transition from day to night and add a touch of elegance to your wardrobe.

Darker shades such as navy or forest green are perfect for fall and winter outfits.

Earth tones like camel or rust for a more subdued look, or go bold with bright colors like yellow or orange.

Check out our trendy suggested looks and patterns below!

patterns used for 90s oversized shirts
examples of 90s oversized shirt styles, colours and patterns

Do Experiment with Different Fabrics

When it comes to wearing 90s oversized shirts, exploring different types of fabrics can help elevate your style while still remaining true to the vintage feel. Here are some tips for experimenting with different fabrics:

  1. Cotton and denim: These classic fabrics can add a laid-back yet sophisticated vibe to your outfit. Try a cotton oversized shirt in white or black for a minimalist look, or go for faded denim to embrace the retro aesthetic.
  2. Silk and satin: For a more polished look, try a silk or satin oversized shirt in that can be worn for casual or formal events.
  3. Flannel: Flannel oversized shirts are perfect as temperatures drop
  4. Corduroy: A corduroy oversized shirt adds texture and dimension to any outfit.
  5. Mesh: For an edgier look, try a mesh oversized shirt over a tank top or bralette. This fabric is perfect for festivals or concerts and can be styled up with chunky jewelry and combat boots.

Remember, combining different textures is key when experimenting with fabrics! Mixing leather boots with flannel shirts, or pairing metallic jewelry with silk tops will add an interesting contrast to your outfit.

It’s also important to note that not all fabrics work well together- avoid mixing too many patterns at once as it can overwhelm the overall look. Instead, opt for one statement piece at a time and build your outfit around it.

Wearing oversized shirts has been popular since the 1990s grunge era when rock bands made them iconic stage attire due to their comfortability and style appeal which revolutionized fashion forever.

Where to Buy Authentic 90s Oversized Shirts

To buy authentic 90s oversized shirts, you need to know where to look. Look no further than vintage and thrift stores, online shops, and marketplaces. In this section of “Go Big or Go Home with 90s Oversized Shirts,” you’ll find solutions on where to buy these iconic wardrobe staples.

Second Hand & Thrift Stores:

Why Use Vintage and Thrift Stores

Vintage and Thrift Shops¬†are a great place to find authentic 90s oversized shirts. These shops offer a variety of unique clothing pieces that you won’t find anywhere else. Here are five points to help you understand the benefits of shopping at these stores:

  • Affordable:¬†Vintage and thrift shops offer affordable prices, making it easier for you to add more items to your wardrobe without breaking the bank.
  • Sustainable:¬†Shopping at vintage and thrift stores promotes¬†sustainable fashion¬†as it gives clothing a second life, reducing waste in landfills.
  • Rare finds:¬†These shops provide the opportunity to discover¬†rare fashion finds¬†that are often difficult to come by elsewhere.
  • Authenticity:¬†Vintage and thrift stores offer¬†authentic clothing from past decades¬†which adds character and uniqueness to your style.
  • One-of-a-kind:¬†You’ll never have to worry about someone else wearing the same outfit as you when shopping at these stores as they only carry¬†one-of-a-kind items.

It’s important to note that some vintage and thrift stores may require extra effort in terms of searching through racks or sifting through clothing piles but the end results can be rewarding.

If you’re looking for something specific, don’t hesitate to ask the store staff for assistance – they may have items in storage that haven’t made it onto the shop floor yet.

Lastly, keep an open mind while browsing through these stores. Sometimes, an item may not look appealing on a hanger but once worn with the right ensemble, it can become a stylish statement piece.

Online Shops and Marketplaces

As you explore the vast world of 90s oversized shirts, obtaining authentic pieces can be quite a challenge. Luckily, various e-commerce platforms and online marketplaces offer an impressive selection. These include highly curated fashion boutiques as well as vast online retailers.

Among these online shops are vintage stores that specialize in 90s clothing items. Here, you will find second-hand shirts that have maintained their quality and are often more affordable than brand new ones from contemporary outlets. Some social media pages dedicate themselves to selling vintage apparel as well.

To add some flavor to your hunt for the perfect oversized shirt, consider browsing through online auctions like eBay or eBid. These virtual treasure troves might unearth some unexpected gems.

Pro Tip: When shopping for 90s oversized shirts online, be sure to check seller ratings and read customer reviews to ensure authenticity and quality.

Get ready to channel your inner grunge with these tips on how to style your 90s oversized shirt like a pro.

Conclusion: Embrace the Big and Bold Trend of 90s Oversized Shirts

The trend of oversized shirts from the 90s is a great way of revisiting cool looks from our past. They give you a huge chance to to make a statement with a fashion style that is undeniably trendy.

The popularity of oversized shirts has grown due to the nostalgia factor as they provide a trip down memory lane for those who witnessed this trend in the 90s, along with their comfort level. There are endless outfit opportunities for any occasion, ranging from casual outings to more formal settings and as a result, the oversized 90s shirts are a staple for everyone.

Our Lookbook and style guide has hopefully inspired your future looks and we hope you enjoyed our tips and tricks for fashioning your 90s shirts in the best way possible! Don’t forget to¬†stand out and express yourself in a unique way that’s true to your own individuality!

Frequently Asked Questions

What are 90s oversized shirts?

90s oversized shirts are loose-fitting shirts that were popular in the 1990s and have made a comeback in modern fashion.

How do I style oversized shirts?

Oversized shirts are versatile and can be styled in many ways. They can be worn tucked or untucked with shorts, jeans, or even a skirt. Layering is also an option with oversized shirts.

What fabrics are used in making oversized shirts?

Oversized shirts are typically made of cotton, denim, or flannel. Some may also be made of silk or rayon for a more elevated look.

What sizes do oversized shirts come in?

As the name suggests, oversized shirts are typically loose-fitting and come in larger sizes than regular shirts. They can range from small to extra large, but it is recommended to go up a size or two for the desired oversized look.

Can men wear oversized shirts?

Yes, men can definitely wear oversized shirts. They can be styled with jeans or shorts for a casual look or dressed up with slacks and a blazer for a more formal occasion.