Should Short Guys Wear Oversized Clothes?

Oversized clothes continue to trend all over the industry, but are they the right choice for short guys? Keep reading for my take on the two-sizes-too-big look.

I’m at an age in which I’ve seen the clothes my peers wore in junior high go in and out of style more than once. I first-hand understand the cyclical nature of fashion, and I’m no longer shocked that nothing stays out of style forever.

Oversized clothes are back. And yes, baggy clothes don’t serve us short gents trying to look taller. And sure, we’re generally trend-resistant here at TMM. Still, oversized clothing is worth exploring. 

You should be allowed to have fun with trends, even if you’re short. Moreover, you just never know. When something goes in and out of style enough times, it may eventually become classic. 

Can Short Guys Wear Oversized Clothes?

First off, short guys can wear whatever they want. But, if your goal is to look taller and perfectly complement your body type, then oversized clothes aren’t the best thing for us smaller folks. Fitted, not tight, classically-cut clothes give shorter guys more presence and don’t drown them.

However, if you’re going to wear oversized clothes, just keep a few things in mind to get the best look out of them. Follow basic clothing structure rules, utilize color, and understand that the best oversized option for a 5’6” guy isn’t the same as that for a 6’2” guy.

Let’s get into the details!

Why Oversized Clothes Don’t Flatter Short Men

By understanding why oversized clothes don’t flatter those with smaller statures, we can more successfully navigate how to wear them.

As mentioned, baggy clothes can drown smaller guys. You get lost in the garment and can also look like a kid wearing dad’s clothes. Both of these phenomena result in you looking even shorter than you are. 

See, baggy clothes create a general silhouette equivalent to a right-side-up triangle. The clothes are weighing you down, bringing you closer to the ground.

Meanwhile, fitted clothes make your shoulders more defined, creating an upside-down triangle (a classic v-shape) and bringing weight and energy to the top of your frame. 

This is all relevant for taller guys, too, but when a 6’5” guy will be weighed down by his clothes, he will still not look short.

Oversized clothes essentially make you look wider and smaller. And based on classic standards for looking good, we don’t want that — and shorter guys have less grace room to play around with looks that widen and shorten them.

How To Wear Oversized Shirts for Short Men

So, how can you wear an oversized top? You can follow general style rules where and when possible. Baggy is the opposite of fit, so standards like “keep the silhouette lines close-to-body” are out the window.

Mind the Shoulder Seems

However, you can still tailor an oversized shirt that fits well on your shoulders. You want the seams to land so that the shoulders of the shirt aren’t sticking out or sticking up. 

This is a key part of pulling off an oversized shirt. Depending on your proportions and the brand and shirt, you may find tops that do this without any tailoring.

Many of these trendier clothes are built to this trend. And at this point, oversized clothes have been back long enough that they’ve likely trickled down to mid-tier brands as well.

With your shoulders in the right place, the rest of the shirt is less likely to overpower your physique.

Pay Attention to Collars and Lapels

This is also the case with jackets. Relatedly, go for thinner lapels, even if the jacket is purposefully oversized.

If your shirt has a collar, go for a style that doesn’t overwhelm your neck. So, opt for an English spread collar over the huge disco-era collars. I know the latter is back in the same way that oversized shirts are. 

So, if you want a bigger collar, just undo enough of the top buttons so that it lays as flat as possible. Again, this is definitely a trendier look, so keep that in mind.

Tuck in Your Shirt

If you can tuck your shirt into your pants, this will make your legs look longer. However, if that’s not part of “the look,” you can elongate yourself by choosing the right colors.

Opt for Monochrome

Monochrome colors are your best bet, especially darker ones. An oversized black, charcoal, or dark navy shirt with pants in a matching color, especially if the shoulders are where they need to be, will have the most minimal effect on your visual height and width.

Baggy shirts naturally add volume to your midsection; if your shirt contrasts your pants, this will further emphasize that. Monochromes create a fluid effect and add to the verticality of the outfit.

Oversized Shirt Color and Pattern Tips

The next best thing is to wear analogous colors, which we go into in our guide to color combinations that make you look taller. Check it out when you’re done here!

This means you’re choosing similar colors that sit next to each other on the color wheel, which tempers the contrast between your top and your bottoms. Some combinations include blue with gray, black with burgundy, and blue with green.

You also want them to be similar in shade, meaning you’d wear medium gray with medium blue, not light blue with dark gray.

I would generally avoid patterns for oversized fits. But if you must, stick to vertical lines, smaller patterns, and low-contrast compositions.

Stand Up Straight

And, of course, stand with confidence and with a proper, straight posture. When you wear oversized shirts, you’re constantly battling the naturally slouchy and short look that comes with it. 

How To Wear Oversized Pants for Short Men

Remember how having properly-placed shoulders can help you pull off an oversized shirt? That’s the same principle when it comes to where your waist lands with oversized pants.

Try Out High-Waisted Pants

Go for high-waisted pants or at least ones that land just above your natural waist. This adds length to your legs. As I suggested, if the outfit allows, tuck your shirt in.

Ditch the Cuffs

Don’t cuff. Just don’t do it. Well you can, but I definitely wouldn’t. As mentioned, we shorter gents have less space to play around with, so anything you can do to elongate the baggy pants, you do it. Anything that cuts your pants off, you avoid it.

If You’re Think, Try Out Regular/Relaxed Fit Pants

Moreover, if you’re a shorter, thinner guy (like me), keep in mind that some regular-fit pants will give the oversized effect visually while still ensuring all of the structure is where it needs to be. 

I’ve found pants labeled relaxed fit that are higher in the waist and look oversized on me. However, they still have clean, uninterrupted lines. This allowed me to wear “baggy” pants without compromising any visual length.

Basically, what’s oversized for a shorter man isn’t the same thing as what’s oversized for a taller man.

Don’t Go Too Wide

Avoid pants that are too wide and bell-bottom-like. They’ll create that right-side-up triangle shape we don’t want. It will also make you look sloppy.

Just because the pants are baggy doesn’t mean they can’t have a bit of a taper.

Pick Tonal Shoes

And finally, go for tonal shoes. Are you wearing black pants? Find some black shoes. Blue pants? Go for the exact shade of blue on your feet, too. 

At the very least, pick analogous-colored shoes. Again, blue shoes with gray pants of the same volume, burgundy pants with black shoes, and so on.

Oh, and boots that add a bit of height won’t hurt, either.

FAQs

Here are a few quick answers to common questions regarding short men wearing oversized clothes!

Can short men wear oversized clothes?

Though oversized clothes will shorten and widen a smaller guy, you can temper this effect by making sure the shoulders are fitted, wearing high-waisted pants, and going for less contrast. But keep in mind that fitted clothes are the most complementary for short men.

Can short men wear an oversized hoodie?

Oversized hoodies can make short men look bulky. However, if you go for thinner weaves, the proper shoulder fit, and pair it with low-contrast pants, you can minimize potentially unflattering effects.

Oversized Clothes for Short Men: Not Ideal, But Doable

I really want to emphasize that oversized clothing is truly challenging for short men. Nothing is going to give us the visual gravitas that perfectly fitted clothes do. It’s more natural, and therefore more naturally attractive, when there’s strength and structure around your shoulders, then a taper to your legs.

But if you want to have fun with trends, your height shouldn’t stop you from doing it!

It’s just that oversized clothing is an active choice for us smaller men. You can’t just throw it on. You have to make sure the colors are right, that the shoulders are at least where they need to be, and that you’re perpetually standing the right way.

It is possible, though, and I hope this guide was helpful in navigating your way through oversized options!

What questions do you have about pulling off more relaxed fits? Let me know in the comment section!