Since 2016


July 20, 2019 8 min read

by Sarah Makhluf

Sarah is a freelance content writer from Boston, MA. She loves traveling, fashion, and the beach.

Oversized clothing has come and gone throughout the last 100 years. Designers are always looking for fresh ways to amp up their collections and stand out from the crowd. While oversized fashion may have been around for almost a century, the trend keeps making its way back into the fashion world.

Is oversized fashion the next big thing? Celebrities like Kanye West created his whole fashion line, Yeezy Supply, around the trend. Pieces from his collection for men and women are cut to be extremely oversized, some even criticizing he went too far with the fashion trend.

While the trend started with women's jackets in the 20s, today, men's fashion has followed suit. From oversized t-shirts, blazers, and leather jackets, designers of men's fashion are quick to jump on board the oversized train.

How exactly did oversized clothing go from shabby to chic? Keep reading to dive into the history of this unique trend, where to find your perfect oversized leather jacket, and learn a few styling tips along the way. While it may not be everyone's cup of tea, more people seem to be jumping on the trend in 2019, and predictions are showing 2020 will be another year for oversized fashion.

The history of "oversized" fashion

You may be surprised to learn just how old the trend of oversized fashion is. History tells us that in Western culture, oversized and baggy clothing came into popularity in the 1920s. By this time, attitudes against women were starting to shift; women were entering the workforce and given the right to vote. Coco Chanel was at the forefront of the fashion revolution for women, offering clothing that was far more mobile and liberating. Relaxed fitting garments began to become more popular as women did not want to be seen as shy and delicate anymore. The famous flapper dress, for example, is a boxy fitting dress made to cover a woman's hips and bust.

Almost a century later, the trend is still making waves in the fashion industry with celebs, bloggers, and Youtubers alike showcasing oversized looks. Especially today, women are wearing men's clothing, and men are more keen on expressing themselves through fashion. Fashion is more gender fluid than ever before, people are more excited to experiment with different looks and trends, and this won't slow down anytime soon.

Oversized leather jacket

What is an oversized jacket

An oversized jacket doesn't mean you're merely purchasing a coat that is two or three sizes too big. These jackets are specially cut to look baggy and exaggerated. The key to oversized clothing is how to find the right one, especially a coat. An oversized leather jacket can add a unique sense of style and flair to anyone's wardrobe. Too much of anything is never a good thing, right? The same goes for your next oversized jacket purchase. It's essential to still choose a size where the jacket won't overtake you.

How to choose an oversized jacket that is still your size

For the most part, standard sizing in men's clothing is XS - 1XL. Remember, an oversized leather jacket should be purchased in your regular size, or maybe even a size down, depending on how oversized the jacket is cut. Don’t feel the need to size up, the jacket may make you look like you're swimming in fabric. The goal is to always remain looking put together and polished, even though your jacket is not form fitted.

How to find the perfect oversized leather jacket?

Finding the perfect oversized jacket doesn't have to be a chore. Check out the list below of the top retailers selling men's oversized outerwear. Follow the tips below to ensure you find the perfect one and what to look out for on your next shopping trip.


Pro Tips:

  • Fit - You shouldn't look like you're about to drown in the jacket. Yes, an oversized jacket is meant to look roomy; there should still be a balance. There should be enough space in the coat for a sweater to fit comfortably.
  • Material - If you're purchasing an oversized leather jacket, be sure to consider the leather quality. Also, which type of animal hide is best for you. The three most common are cowhide, sheepskin, and lambskin. With lambskin being the most expensive and softest, and cowhide being the most cost-effective and durable. Sheepskin falls in the middle price point of the two and is also known to be ultra-soft while still being able to hold well against normal wear.
  • Leather grade - The best leather grade money can buy is full-grain, with top-grain coming up second, and thirdly is genuine leather. The cost of your jacket will be determined by which leather grade you chose, and which animal hide you prefer.

Where to buy an oversized jacket

Neiman Marcus

These popular department stores sell everything under the sun, including some great options for men's oversized jackets. Easily found in malls around America, this is a great place to check out if buying online isn't your thing. They have plenty of in-store options to try on, and a sales associate is usually on hand to offer extra assistance.


This online retail store hails from the UK, but they ship worldwide and offer a vast range of reasonably priced clothing for men and women. Their men's oversized jacket selection is quite impressive for an online store. If you chose to shop with them be aware their sizing is geared toward men in the UK, so be sure to convert to your US size before ordering.


Zara is known to always be on top of the current trends. This fast-fashion clothing brand caters to men looking for the latest styles without having to break the bank. Their collection of oversized men's outerwear is one of the largest selections we have seen. Shop online or in-store to find the perfect oversized coat.

Urban Outfitters

One of the top places millennials like to shop is 'urban.' Urban Outfitters are sometimes known to push the boundaries of fashion and offer men and women on-trend looks. Their clothing is moderately priced, and the stores can be found in malls and shopping centers across the US. If you are looking for a unique oversized jacket that won't break the bank, be sure to take a look at Urban Outfitters.

Styling an oversized jacket

Custom made oversized jackets

If you haven't had much success finding the perfect jacket in stores, going custom is highly recommended. Having your oversized jacket custom made gives you the freedom to choose the exact material, lining, color, and fit you desire. Where an oversized jacket can be hard to fit, going custom may be your best bet. Custom clothing, in general, is on a considerable rise within the fashion industry and is becoming more easily accessible. If you have a unique size, like big and tall, or maybe you need a more petite size, custom made covers it all. Check out some of the top online shops for all of your custom made leather jacket needs.


Leather Jacket Master

This online store has countless options for custom made leather jackets to choose from. Each of their coats is handcrafted and before ordering customers are asked to select their preferences for their jacket and get a quote on the final price. The quote does have a $10 non-refundable fee, but they promise exceptional customer service and guidance throughout the whole process of getting a jacket custom made.

The Jacket Maker

They make custom leather jackets for men and women at the Jacket Maker. Try shopping their online selection to find the perfect oversized leather jacket. Their process is a breeze as well, the site is user-friendly, and your custom made leather jacket should arrive within a couple of weeks after ordering.

How to measure yourself for an oversized leather jacket

What's important here is to follow the size guide on the site you choose to purchase your oversized leather jacket from. Grab a tape measure and measure your chest width, sleeve length, shoulders from tip to tip, and your back lengthwise. You may need an extra set of hands here to ensure you're getting the exact measurements. Follow the guide to ensure you're purchasing the correct size, or if you're going custom add your precise measurements on the online form. While oversized jackets are not designed to fit perfectly, they should still look somewhat tailored on the body.

PHYSICAL - The Admiral Moto

PHYSICAL - The Suede Double Rider

PHYSICAL - The Technical Bomber

Styling an oversized jacket made specifically for you

Have you found the perfect custom made oversized jacket? Need some tips and tricks to style your oversized coat and still look tailored? Follow the easy guide below to always ensure you look polished and put together in your oversized outerwear. Once you have the perfect fitting jacket, the rest is easy, have fun playing around with different looks to keep your wardrobe exciting. Try picking up some new accessories and shoes to match your new jacket and create countless looks. A custom made oversized leather jacket is something that will be in your wardrobe for years to come, think of it as an investment piece. With proper care and minimal maintenance, a leather jacket can not only last for decades but continue to look as good as new.

  • Keep it simple - Try pairing your oversized jacket with slim-fitting slacks or skinny jeans, wearing baggy pants with a loose-fitting coat could make you look frumpy and not put together. Finding the perfect balance is critical here, so keep it simple on the bottom, wear neutral colors and look for pants with a slim fit or bootleg fit.
  • Accessorize - Adding a belt and a great pair of shoes will compliment your oversized jacket perfectly. Steer away from adding a scarf to this look; it may make you look too top-heavy. Instead, for colder days, try pairing your oversized jacket with a wool beanie.
  • Let the jacket do the talking - Without a doubt, an oversized coat is a statement piece, you don't need to add any more frills to an outfit if you already have your main focal point. Keep the rest of your outfit casual and let your oversized jacket stand out.
  • Don't over layer - Try wearing a plain slim fitted t-shirt under your oversized coat instead of something bulky like a thick sweater. This may create a look that is too boxy and can look unkempt. Aside from that, it will also be uncomfortable if you already have extra material from the jacket, keeping your shirt underneath light will allow you to move around more freely.

We want to hear from you and if these oversized leather jacket outfit ideas were helpful! As someone passionate about fashion writing this article was extra important to me. I think we can all express ourselves through our clothing and use style as a way to showcase our unique personalities. Never be afraid to try something new when it comes to clothing, maybe oversized jackets are out of your comfort zone? If so, that's ok! Next time you're out shopping try one on and see how you feel; you may find your next favorite piece of clothing. Did you like this read? If so, leave us a comment below telling us why, or what your favorite type of leather jacket is. Please pass along this article to friends and family looking to add a little spice in their everyday wardrobes.

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