Let’s skirt around the shirt issue no longer, as we now urge you to befriend a vintage oversized shirt today! You will reap the benefits for years to come, believe us.

man wearing a button down vintage shirtRegular readers of our blogs will be more than a wee bit familiar with the much vaunted vintage oversized look we love to showcase in our Mystery Box range as well as across many of our individual items dropping to our site, be they hoodies, windbreakers, cargos or coats. But the humble shirt has perhaps not been a top pick to sing and dance about, as it has somewhat meekly allowed itself to be overshadowed by its brash, infinitely versatile and perennially popular friend, the T Shirt (three blogs and counting!).

Why, the shirt has even allowed itself to be neatly sidelined by its could-be companion piece the oversized jacket, which managed to cheekily grab a whole expose to itself How To Wear An Oversized Jacket With Style. But no, enough is enough, and we are banging the drum today for the oversized vintage shirt, in all its glorious variations of texture, cloth, style, colour, pattern, fastenings, sleeve length and price. Grab yourself a classic Denim, Aloha or Oxford variety now, and join us on this epic voyage into the styling of an oversized vintage shirt.  


women wearing a shirt with a sweater vest

Basics of Styling Oversized Shirts

Not Too Baggy!

The key here is slightly oversized but not too baggy – we defo don’t want muscle or slim fit shirts showing off every toned body contour, but nor do we want you to lose yourself within extraneous folds of an uber-baggy number! Take a look in on our blog Oversized Outfits - Everything You Need To Know to help firm up your ideas on the non-tight look.

Undo Those Buttons

To ensure a casual look to your oversized vintage shirt style, we say, loosen a few of those there top buttons to expose some skin. This adds instant interest to your look – view it as a sort of quickfire way to add a layer with minimal effort. And of course, this also allows for a sneak peek of a tantalising accessory necklace lurking below. The icing on the proverbial gateau.

Accessorise Your Neckline

As mentioned above, adding a simple chain, with or without an accompanying pendant, really amplifies your vintage oversized shirt, either with top button(s) undone or with your chosen oversized shirt neckline naturally exposing your neck detail. Don’t forget, shirts come in many variations, with the neckline being no exception to the choices available, so don’t just stop at classic collared, when there are so many others besides.

Roll Up Your Sleeves / Loosen Your Cufflinks

To make your chosen oversized vintage shirt look extra casual, it’s always good to roll up your sleeves, just one or two turns, to send out the message that you are ready for what lies ahead! Likewise, just unbuttoning the cuffs, leaving a relaxed appearance to all who look on you. Subtle simplicity at its finest, but so effective.

Oversized Vintage Shirt Outfit Inspo For Guys

  1. Smart But Casual

There’s the conundrum, you say?! Why, not at all, we respond! Go for a minimalist look in your vintage shirt by choosing a garment uncluttered by logos and stitching details to start with. A classic Oxford shirt lends an instant clean vibe which is desirable for any everyday occasion of a casual nature. And, as with anything holding Oxon credentials, this shirt also exudes smart. So, within one shirt choice, the smart casual vibe is cleverly combined in one.


casual smart shirt outfit

  1. Tank Top / White Tee Underneath

Slipping on a classic white tee base layer first turns your oversized vintage shirt into a cunning overshirt. Easy. Equally, throwing a sleeveless sweater vests over the top of your vintage shirt is another awesome way to add dimension and depth to your oversized shirt look. Try this out with a classic flannel number or head into another sphere by tracking yourself down a one-off dress shirt. Who said, you couldn’t mix up ideas to produce a truly unique look? Not us!


white tshirt underneath shirt outfit

  1. Shortish Shorts + Baggy Shirt

Achieving a contrast by coupling a vintage baggy shirt with a pair of shortish shorts (not too short) gives a really effective look by effortlessly providing the perfect silhouette for this kinda summer fit. Try it out with a short sleeved collared shirt and pop a pair of sunglasses on to give yourself all the appearance of the most intriguing guest at the summer do.


shirt + shirt outfit

  1. Oversized Everywhere

OK, enough of going easy on you, now consider getting yourself out there by pairing your chosen oversized vintage shirt with an equally baggy pair of jeans or chinos for the must-have oversized vintage aesthetic. Vintage baggy through and through. How we all love it! Not convinced? Take a look at our blog: Why Is Oversized Clothing Trendy?


shirt outfit oversized look

  1. Go Monochrome

Moving on to the hue of the outfit, rather than the silhouette, here your options are as endless as the colours of the rainbow. But before you get carried away in a riot of unruly shades, we are focusing here on a one colour does all look. Less certainly is more with this vibe and getting the tones of the top and bottom half to nearly or completely match is a skill well worth cultivating. We rate denim and experimenting with double denim is certainly a worthy Y2K contender for your starting point here.


monochrome shirt outfit

  1. Pattern Like Crazy

Yes, you knew we could not resist this outlandishly unique look for much longer! Turn a few heads, why don’t you, by chucking on a patterned shirt every once in a while! Our top ideas include these stunners for starters: lumberjack, Hawaiian, striped, cartoon prints, floral, tie-dye, paisley, colour block … let your imagination really run riot with shirty ideas.


patterned shirt outfit

Oversized Vintage Shirt Outfit Inspo For Gals

  1. Front Tuck + Shorts

If you’re after a casual, laissez-faire kinda vibe, simply pair your oversized vintage shirt with denim shorts. Start by front tucking the shirt into your shorts to give yourself a defined waistline, then complete the outfit with a pair of trainers or sandals for a comfortable and chic ensemble that’s perfect for heading out on a day with the group or just cracking on solo with your to-do list.


shirt outfit with tucked in shorts

  1. Belted + Wide-Leg Trousers

Elevate the summer front tuck style from above by adding a dash of sophistication to your oversized shirt plus bottomwear co-ord. Two pieces and a belt say it all! Choose a statement belt to cinch the shirt at your waist as you pair it with wide-leg trousers. Then you’re good to head off with ease and elegance ready to attend more formal events or even a work-facing gathering.


tucked in shirt with jeans outfit

  1. Effortless Boho: Maxi Skirt + Sandals

For a slightly (well, please apply your own take on this qualifier) less conventional ensemble, pair your oversized vintage shirt with a lightweight flowing maxi skirt in earth neutral tones to bring out your boho vibe. Complete the outfit with a pair of sandals or even have ankle boots peeking below to achieve the epitome of out-there-dom! Give this outfit a whirl at your next music festival, summer BBQ event or while on a summer tour with your camera catching the iconic sights of any city.


maxi skirt outfit women

  1. Leggings + Super Baggy

Sporty fans will defo fall for this classic easywear outfit. Leisurewear with a shirt, we salute you! Style your oversized vintage shirt with a pair of leggings and simply pop on a pair of your fave trainers, skate shoes or even high-tops. Job done! The dimensions, both in breadth and length of your shirt here, can be left entirely up to your inclination on the day. Feeling like a cover-up? Choose a super baggy shirt. Feeling a little less freeflow? Just incorporate a belt, reduce the fabric amount and you’re good to go.


shirt outfit with leggings

  1. Sweater Vest

The sweater vest look is not to be confined to the domain of the chaps Chandler Bing, so grab yourself your own number, bearing in mind that an out-there vintage shirt (see Pattern Like Crazy above) might be looking to partner with a more subdued sweater vest. But then again, who are we to limit your individuality in all things style?! Add a sweater vest on top of your oversized vintage shirt to add layering, keep you a lil warmer and end up looking very much THE part.


sweater vest shirt outfit


To sum up, the joy of the vintage aesthetic oversized shirt, is not a newly invented 21st century phenomenon, but has been nestling among us ever since humanoids started favouring a shirt as a functional layer of clothing in their wear. From 60s flowerpower cheesecloth shirts, loosely tied at the waist by the wearer, to the 00s re-emergence of the Henley shirt, shirts have always been part of the fabric of our lives.

Shirts no longer just afford the buttoned-up look our forefathers might have been duty-bound to don for the office back in the day, but now shirts are wondrous items of apparel, which you can adapt to make your own. What goes around, comes around as the saying reminds us, and shirts are an excellent and ecological example of this maxim. Hats off to the shirt in our life! 

  • Follow our socials to be the first to hear what’s happening  
  • Tap here to check out our latest drop of vintage heaters from the 90s–00s


HF Lanzer
Tagged: Style Vintage