Vintage Baggy Style

Two of our favourite words: ‘Baggy’ + ‘Vintage’. And would you adam and eve it, but they’re trending right here, right now in our post-pandemic 2022 days. As we speak. And we’re embracing this infinitely adaptable, yet mahussively stylish fashion wave which crashes in among us at surprisingly regular intervals. Not only does it give us all the opportunity to express ourselves in a comfortable, loungy manner, but it also allows for a significant element of creativity and flair (well, yes, also flare as far as baggy trousers are concerned!) to be incorporated into our outfits. The end result: a truly authentic and unique YOU, especially when vintage apparel is the key player.


Vintage baggy style

Of course, you can always go baggy, baggy, saggylicious all over, but we are looking for a slightly more nuanced approach here in our idea of what makes an effective oversized outfit for our current times. Maybe an underlayer turtle or crew neck can serve as the foundation for a baggy college sweat, or a smart shirt first, with a generously roomy jacket on top. The contradiction is definitely attainable with a little bit of effort and know-how from, you the wearer: relaxed, but still maintaining an element of crisp.

Step aboard with our blog, and you’ll soon be repping the look enjoyed by many earlier generations in their eras, such as 60s hippies, 70s new romantics, 80s rockers, 90s hip-hoppers, 00s rappers and Y2K boy bands – all these groups incorporated an element of the oversized into their outfits, while they revelled in the self-expression available, once the shackles of restrictive formal clothing are removed.

What is an oversized outfit?

Let’s look at what we are actually talking about as far as the loose (no pun intended) term ‘oversized’ is concerned when it comes to discussing trendy outfits. The kind and giving oversized partner or older (i.e. bigger!) sibling sweatshirt or joggers can be as slouchy and generously proportioned all over the place as you like, but some oversized items, such as t-shirt, hoodies and shirts do well with a little gentle guiding towards the style we’re aiming to capture: think of these pieces as your collection of carefully curated casual cool clothes, rather than the instant credentials provided by multiple XXXXXX on the label.

So, we are looking for clothes which are certainly larger than your normal size and lacking any trace of a descriptor such as ‘fitted’, ‘tapered’, ‘tailored’ or horror of horrors ‘slim fit’, but which will still appear to have enough shape and form to them to avoid an unwanted and rapid descent into slobwear. Our recommended starting point for this, has to be the vintage rails which are crammed full of quality cotton and wool pre-loved gems, which will tick all the boxes in the search for your array of oversized clothes.


Vintage baggy style

Why should you rep the oversized style?

The oversized style is a relaxed, welcoming one which is certainly great to adopt. Anxiety levels can be lowered as the clothes look after themselves and do not put any additional stress and discomfort on the wearer. To sum up, the key features and advantages of wearing oversized outfits include:

  1. Super comfy – think Fila fleeces, Kappa popper tracksuit bottoms and Harley Davidson T-shirts
  2. Trendy, hence look stylish – think Yves Saint Laurent shirts, Timberland hoodies and Nike puffer jackets
  3. They don’t make you feel constrained – think Carhartt cargo trousers, Adidas winter coats and Champion long-sleeved tees
  4. Easy to style – think Ralph Lauren zip-through hoodies, Polo Sport rugby shirts and Ellesse crop tops.

Why choose vintage?

Oversized was trending in the 90s and early 00s, so the pieces available now within the retro movement were the original oversized garms worn by those earlier generations! It’s hard to argue against vintage garms being the first port of call when it comes to styling an oversized outfit: the material is better quality on the whole; every item is sustainable, thus avoiding further damage to the environment; each item is now a ‘one of one’ number, so not available as a standard look for the masses; the items have been through the lifecycle of wash, wear, wash again, so there are no shrinkage issues to take into account once you have lovingly curated your outfit. A new oversized outfit can sadly go from oversized to skinny with one quick wash, whereas vintage gives you an outfit to last!


Vintage baggy style

How to rep the oversized style

If you’re looking to rep an oversized t-shirts, we have a full blog about this here that explains this look in considerable detail. On this page, we are concentrating our attention on the finer points of  how to rep an oversized outfit in general.

1. Stay near your size

  • As we advised earlier, don’t rely simply on XXXXXX on the label for your oversized look, but choose clothes slightly larger than your normal fit, watching out for ‘oversized’ in the product titles. Make sure the items still fit in crucial places, such as your shoulders and waist.
  • Like everything fashion-related, it is a matter of trial and error in front of the mirror, so experiment first with one or two sizes larger, using items borrowed from friends or family, and make a note of the ideal measurements once you find a fit you are happy with.
  • Remember, there are no rights or wrongs here, but it is more a matter of you finding the size which suits your personality and the look you are aiming to rep, top and bottom.
  • Size indicators given on labels are not always that useful, especially where vintage clothes are concerned, so please check the actual measurements carefully each time.

2. Experiment

  • The most important thing for facing the world in your oversized outfit, is to experiment further to discover what you’re comfortable and confident with.
  • Maybe start slow with a simply oversized plain tee, and then move to the bottoms and in no time, you’ll know exactly what you can get away with when it comes to your body and personal style.
  • The term ‘outfit’ can be applied loosely here, as maybe you will just want to go for an oversized top … or bottoms … there is no pressure to go full house if that just is not ‘you’.
  • Be comfortable in your skin, be comfortable in your choice of clothes – our first rule of fashion.

3. Try to avoid completely plain

  • With an oversized item of clothing, you also need to consider the colour (see 6 below) and pattern you’ll be showcasing – it’s the detail which counts, and in this case a small amount of detail can go a long way to distract from the mass of fabric the clothing item itself affords.
  • We’re thinking here of a vintage graphic t-shirts, a discreetly embroidered logo on an old-school Napapijri sweatshirt, a Levi’s denim jacket with sewn detail or a minimalist print, all of which will make your oversized item stand out from the crowd.
  • You don’t have to go full crazy acid wash or tie-dye sweaters here, as that can be over-distracting, but consider looking at geometric and abstract designs to add accent to your outfit.

4. A good rule of thumb

  • If you are wearing baggy up top (shirts, gilet, knitted sweatshirts, etc.) then keep the rest of your outfit quite fitted and/or structured to serve as a neat contrast.
  • If you are wearing baggy on the bottom (pants, jeans, trackies, shorts etc.) then the same rule applies in reverse. A slimmer fit top here can finish the outfit off brilliantly, without distracting from the overall baggy look.
  • However, if you’re feeling ready for it (perhaps you are a risk taker?!),  you can go baggy on baggy and pull it off, as we explain here, but please take care, this look is not as straightforward as it seems.

5. Accessories and shoes

  • Look to statement indie accessories to complement your oversized outfit. Bold necklaces, earrings and bracelets along with a Nike bucket hat, a Burberry scarf, belts and bags can all play a role in the bigger picture here.
  • While your oversized overlayers provide you with a flowing silhouette, accessories are the perfect device to stylise your look and make your individual presence felt.
  • Choose suitable footwear for your oversized outfit. Clearly, we are not recommending going big on the size here, but chunky, bulky retro trainers, high-tops, boots and Timberlands all work amazingly well to round off an oversized ensemble.
  • Again, have fun experimenting in your local thrift store to see which style footwear looks the best with the outfit you have chosen.

6. Colours

  • Why are neutral tones so very popular among fashionistas repping the oversized look today? Well, these more muted and subdued colours are endlessly adaptable and very easy to combine within a flexible wardrobe.
  • Not surprisingly, this is also what makes them a crucial component of a sustainable vintage clothing collection: one tone fits all, rather than a one-off bobby-dazzler which may be too eye-catching for its own good.
  • But, this doesn’t mean you cannot go for vibrant accents – think of yellow, orange, multi-colour, red highlights for starters – these colours will ideally work alongside the plainer shades within your outfit, rather than dominate the end result.

7. Take inspiration

  • Words can only help so much when referring to fashion and ‘how to wear’ a specific type of outfit, so we thought providing you now with lots of different images that we love would help you out a lot more than us just blabbering on and on and ....
  • Taking inspiration is defo the best way to grasp and gain a clear understanding of how to rep the specific fit of ‘oversized’, so here you are:


 Women's inspo

 Over shirt

 Full baggy style

Vintage Baggy Cargos

Vintage Baggy Tee

Vintage Baggy Outfit

Vintage Baggy Puffer

Vintage Baggy Sweater Vest

Vintage Baggy Sweat

Vintage Baggy UnderShirt

Men's inspo


Vintage Baggy Varsity Jacket
Vintage Baggy Jeans
Vintage Baggy Tee

Vintage Baggy Cargos

Vintage Baggy Jacket

Vintage Baggy Hoodie

Vintage Baggy Layers


We really hope you now feel equipped to source and style your perfect vintage oversized outfit, decide how best to accessorise it and will soon be ready to step boldly forth into whichever engagements and activities lie ahead for you. The main thing is that you can constantly update and amend your outfit, so you remain fresh even when wearing basically the same garms – a little casual tweaking here and there will keep all your social contacts and photo messages guessing, as to just how you are next going to appear in your cool oversized outfit. After all, you wouldn’t want to become predictable, would you?!

We’d love to see what style you develop yourself as far as all things oversized outfits are concerned, so please share your style ideas and photos on our Insta and we can all enjoy the diversity of looks you have achieved.

HF Lanzer