Why You Look Bad in Oversized Clothes

The oversized aesthetic trend seems to be everywhere, but going big is one of the biggest mistakes you can make with your clothing, literally. Just before we get started, it’s important to state that, if you’re intentionally going for oversized clothes, you are free to make that call. After all, we don’t want to stop you from experimenting with your style; but as your fellow classic style enthusiasts, we wanted to explore the fine line between “comfortable and cool” and “big and boxy.”

So, consider the points today as exploring the realities of oversized clothing and why participating in this trend might not be the most flattering for your body type. In other words, we don’t want you to look back a decade from now and go, “Man, what was I thinking?” So, let’s get started with the first issue of oversized clothing.

1. They Don’t Make You Appear Bigger

While fit in menswear can be a bit subjective, there’s a huge difference between the drape of the 1930s and MC Hammer’s parachute pants. You might think oversized clothing will help give the impression of your body having added bulk. In reality, the opposite often happens as the extended seams go past your shoulders and torso, making it appear as if they’re shrinking your frame.

The larger armholes and sleeves will make it appear as if your arms are much smaller since they don’t fill up those holes. You shouldn’t overcorrect this either by going too small and too tight which whould become increasingly uncomfortable over time with your limited range of motion.

You may also appear as if you’re wearing someone else’s clothing. If you’re intentionally cultivating this look, all the more power to you, but if you’re trying to create the classic aesthetic we promote on this channel, this trend won’t be your most effective option. Instead, we recommend looking to the Golden Age of Style for inspiration.

Clothing tailored to classic conventions can help you look bigger in the best way possible, helping to balance out your proportions as a neatly fitted waist and clean line on your pants could also make you appear a little taller; jackets with a full chest and arms will still appear elegant, all while giving extra bulk; and a jacket’s tapering around the waist helps to create that desired V-shape, something that is often desired in the male figure as opposed to just a potato sack, big all-around aesthetic.

2. They Don’t Make you More Masculine

Oversized clothes aren’t inherently more masculine than fitted clothes. One of the biggest hurdles many of his face especially at the start of our style journeys is the perception that well-fitting clothes or even caring about how you look in your clothes is effeminate.

This outdated stereotype, that taking pride in your appearance excludes you from the “real men’s club,” started picking up steam in the 80s and has fortunately become the new norm in many parts of the world. However, this is a recent societal invention, something that couldn’t be farther from the truth. After all, no one ever called Gary Cooper or Humphrey Bogart effeminate for wearing well-tailored clothing. Not to mention, historically, men were often the ones to wear peacock outfits, not women; showing just how malleable these norms truly are.

As we’ve mentioned previously, well-tailored clothing actually accentuates the idealized classic male form and you shouldn’t let others scare you from expressing yourself. In fact, you’ll probably be pleasantly surprised by the compliments you’ll get from wearing a well-fitted suit or jacket from both men and women alike, as Raphael outlines in our other guide.

3. The Look Isn’t Timeless

It is the ultimate cornerstone to consider when following the classic guidelines of being well-dressed, and while some modern fashion trends are advocating for oversized clothing, they won’t last.

Throughout history, oversized clothing has come in and out of fashion as a status symbol and first rose to prominence during the Medieval Era as cloth was far more expensive to manufacture and clothing had to be made entirely by hand, and those well-to-do intentionally ignored the realities of human proportions to show off their wealth, also known as the historical equivalent of a Hypebeast Flex. Common examples included cape sleeves, the exceptionally broad shoulders, typical of the Tudor Period, and pumpkin breaches.

These clothing styles were intentionally exaggerated in order to require additional fabric to show off that the wearer could afford that extra fabric in the first place, and while these more extreme examples have faded away, generous fits have already come in and out of fashion several times over in the last century alone; though, not all of them strayed into oversized territory.

The mid-30s had pants and jackets that were relaxed and looser but without losing their structure, while the late 40s got a little boxy and started to push the line on what we consider well-fitting today, and the 80s and 90s took the 40s drape and exaggerated it into a more extreme version, ultimately appearing dated and even costume-y. We rest our case.

But, seriously, anytime extreme proportions are utilized in clothing, they only work for a very small minority with that body type, and unless you’re in that minority, the harsh truth is that it just looks exactly like what it is: a passing trend.

Instead, we feel that it’s better to follow tried and true principles that have remained the same over decades and develop your own personal style, such as focusing on quality fabrics, classic colors, proportionate fits, and utilizing patterns that best complement your physique so you have more money in the long run and just look better in the process.

4. You’ll Be More Uncomfortable

The whole point of wearing baggier clothing is to be more comfortable, isn’t it? While it’s true that sausage fit skinny jeans and other tight-fit styles can be uncomfortable to wear, baggy clothing will eventually do the same thing even if it’s not immediately noticeable when wearing it. But, how could that be?

The biggest issue with oversized clothing is that we’ll have excess fabric which will rub together with each movement you make, meaning that it’s much more likely to pill, causing rashes or impede movements in other ways; not to mention that oversized shoes can cause blisters and can make walking a literal pain.

If there’s one place that you can’t afford to risk being oversized, it would be your shoes, and while some wear and tear on your clothing is normal, the excess amount of fabric in oversized clothing is going to wear out much quicker; plus, you’re bound to have posture issues if your clothing is oversized since you’ll constantly have to stoop or readjust your clothing to make sure that it sits properly, which could lead to bad posture or health problems later down the road if that were to become your default stance; not to mention becoming a health and safety hazard when you inevitably trip over your larger than life pant legs or get whisked away in the breeze by your cape-like T-shirt.

5. Most Materials Don’t Function Well When Oversized

While if you just go with well-fitting clothing, it will have an average lifespan, most materials don’t function well when oversized. While some fabrics might function acceptably within the context of oversized clothing, most of the natural materials that we advocate for here at the Gazette won’t work optimally for this trend.

For example, a Super 120’s wool fabric could work wonderfully for a Neapolitan jacket made with classic proportions, but would be flumsy, feeble, and prone to pilling if it was used to make an 80’s style oversized suit. This is primarily because a fine wool fabric like this can only take so many rubs together before it starts to fall apart, and this will happen even faster if it has more wool fabric to rub up against.

Many of the classic style patterns we love also won’t scale properly when utilized and oversized clothing. Take pin and chalk stripes. The vertical lines are designed to elongate the wearer and make them appear more trim; however, this design will fall apart if the pants are puddling and the sleeves are extended past your wrists since the puddling fabric makes the wear appear shorter and will clash with the intended effect the stripes are designed to have.

6. It’ll Throw Off Your Entire Ensemble

You could wear a jacket made from the nicest vicuña in the world, but if it doesn’t fit right, you’ll never look as good as the guy wearing a cheap jacket that fits him well. Clothing that is too baggy will never look like it was made for you, instead people might assume that your uncle gave it to you instead.

When many here at the Gazette started our style journey, we often wondered why we looked more like Peewee Herman than James Bond in our clothing, and this is usually the biggest culprit behind it since the construction methods and styling are just the frosting, but the fit and the proportions are the cake. If you ever have to compromise between fit or anything else, fit will always be what will set you apart, as even a cheap garment can look great if it fits well.

Many generous garments can be balanced with a proper awareness of proportionality. More generous oversized shoulders balanced by a narrow waist is something that you often saw in the 1950s. A good point of balance can make the entire ensemble appear perfectly sized, even if an individual element might appear oversized. But, without that point of balance, the entire ensemble can be compromised.

A perfect example of this is comparing the 30s to the 80s. The 30s suit was baggier than what we’d see from a contemporary suit today, but all the elements of the jacket, like the lapel gorge, width, length, and shoulders, were designed to complement each other, along with the trousers, which were also proportioned correctly with harmonious elements, like drape, cuff type, and size. Even the design of the dress shirt and accessories— like neckwear, hat, and jewelry were selected to be proportionate to each other.

An 80s suit just exaggerated the width of the suit from the 30s without keeping many of these other elements in mind, leading to oversized garments that just look weird when mixed with a shirt, tie, or other elements of an outfit, showing just how important balance can be. 

7. You’re Lowering Your Confidence

Finally, wearing oversized clothing can affect how you perceive yourself, even if you don’t notice it consciously. Often, while trying to hide your body, you become more self-conscious of yourself while out in public, and this discomfort in your own skin can be something others pick up on, creating a vicious feedback loop that can hurt your quality of life without you even noticing it. It can also make you feel subconsciously a little juvenile. And while there’s nothing wrong with being young at heart, not considering how to address your age can limit your style potential.

By having the confidence to wear well-fitting clothes that present your body in the best way possible, your self-esteem will be boosted, leading to a much more positive loop with others. Who knew that clothing could be so philosophical?

Conclusion: Oversized Clothes Aren’t for Everyone

We hope this guide has helped to differentiate the differences between well-fitted drape and oversized clothing, and how classic style seeks to encourage clothing that isn’t oversized. We think that you’ll find that having an eye for what is and is not proportionate on your frame can be one of the biggest quality-of-life improvements you can make because, while there’s nothing wrong with intentionally embracing oversized clothing if you enjoy it, unintentional oversized clothing is definitely fit that won’t do you many favors.

What’s your take on the oversized clothing trend that we’ve been seeing resurgence?

Outfit Rundown

Today, I’m wearing a green, double-breasted jacket with a tan T-shirt, green trousers, brown dress shoes, brown belt, and a Fort Belvedere pocket square. The pocket square has green and blue accents with a tan trim around the edge. My fragrance for the day is from Roberto Ugolini, and it’s called Blue Suede Shoes.