So, you’re a bigger guy, and you want to dress well, but you’re not sure where to start.

Maybe you can’t find clothes that fit right, or you just don’t know if something looks good or not.

Sound familiar?

Well, I hear ya, and I know where you’re coming from.

I used to be a big guy myself—I’m 5’9″ and 15 years ago, at my heaviest, I was 241 lbs and pushing a 40″ waist (!)

B a long time ago

Me in my early 20s and 80 lbs heavier than I am today

Luckily (for you), I was always into fashion and my own personal style, so I picked up some tricks along the way that applied to both my bigger self as well as when I was losing weight.

So if you’re looking to dress sharp as a big guy, just follow these tips I’ve laid out for you in this article.

Fashion Tips For Big Guys… in a video?

Damn right!

In the video below, I’m laying out 5 tips to get you started on the right foot. These will apply no matter the kind of style you’re going for.

Hit Play to watch (and subscribe to Effortless Gent’s YouTube channel if you haven’t already!) or if you prefer, continue reading below.

Big Guy Style Tip #1: Understand how clothes should fit YOUR body

So, how exactly should clothes fit on a bigger guy?

You want to use the same fit cues that every guy should use. Your shirts and pants should fit close to your body without being too slim and tight, and also without being too big.

For example: With woven shirts (like collared dress shirts and sport shirts), first make sure the shoulder seam is sitting directly on top of your shoulder bone.

big guys: how a shirt should fit

Shirt and pants from Bonobos

From there, how far away can you pull your shirt from your body? If you can pull it away 2-3″, that should give you enough room to move comfortably and sit down while still pulling off that slimmer, more tailored fit.

For pants to fit, they can be a bit closer to your legs, and you want to make sure there’s little to no break (meaning no excess fabric bunching and pooling at your shoes), and a slight taper from the knee down.

You want to avoid excess volume wherever possible, and having a tailored pant leg with little to no break makes you look slimmer.

Big Guys: How slim pants should fit

Bonobos has plenty of choices for big guys

MINI TIP: Sit down in the fitting room when trying on clothes.

Shirts and pants may look good standing up, but when you sit down, it might be a completely different story.

Maybe the shirt is too tight and you can’t move your arms, or the buttons look like they’re gonna pop.

Maybe the pants are too tight in the thighs when you sit, or the waist is simply uncomfortable.

Clothing should be comfortable when seated, as well as when you’re up and walking around.

By the way, tailoring is everything!

Go to a tailor whenever necessary to achieve the best fit; most likely, clothes won’t fit you well off the rack, so this is the extra step you must take.

And you’re not alone; pretty much everyone (aside from models whom most clothes are designed for) has to do this to achieve a tailored fit with off-the-rack clothing.

Big Guy Style Tip #1B: Find cool brands that make your size, and stick with them

If you watch other men’s style YouTube videos, or simply look at models in magazines or in stores, you might think your clothes should / will fit like theirs.

Well, it won’t.

It’s important to find the clothes and brands that work best for your body type.

Yes, that requires you to do a bit of leg work but once you find the brands and fits that work best, you can stick with that brand for life.

Here are two great suggestions to get you started:

Bonobos: Smart, sharp casual fashion for big guys

big guys: bonobos extended data-lazy-sizes

I love Bonobos for classic smart sharp looks, and it’s a brand I’ve shopped for years.

They recently introduced extended sizes, so basically, their same great clothes but made for bigger guys.

Check Out Bonobos here »

MINI TIP: Go shopping and try on clothing in the afternoon or evening instead of in the morning.

You are your slimmest in the morning and your body expands and gets bigger throughout the day—you rehydrate, you eat meals, you move around, you sweat, etc.

If you shop and try on clothes early in the morning, what feels like a great fit then, may be uncomfortably snug by day’s end.

So, if possible, shop and try on clothes towards the end of the day.

ASOS: Affordable casual and streetwear looks for big guys

big guys: asos plus data-lazy-sizes for men

ASOS sells casual clothing and streetwear fashion in standard sizes as well as bigger sizes. They have a whole plus size shop that sells awesome (and affordable) streetwear.

Keep in mind, this is more trend-forward stuff, but if that’s your jam, I’d start looking here.

Check Out Asos here »

Big Guy Style Tip #2: Buy affordably (for now)

Trust me, I’m all about buying investment-worthy pieces that look and feel great, that you enjoy wearing, that have great brand reputation and recognition, and are a pleasurable experience to own overall.


Your body changes a lot as you lose weight, so assuming you are on that journey of dropping the pounds, it’s a good idea to buy affordably first.

fat to skinny celeb transformations zach galifianakis john goodman

Save the investment-worthy pieces for when you are at your ideal weight or body composition.

And once you hit your goal, treat yo’self! Grab those higher-quality Lean Wardrobe pieces, knowing that you won’t be having to replace them any time soon.

fat to skinny celeb transformations seth rogen adam richman

Side Note: Follow big guys who dress sharp on Instagram

Of course, Instagram can be a huge source of inspiration when you’re trying to figure out how to dress. Follow these stylish bigger guys on Instagram and pay attention to how clothes fit on them.

great instagram accounts to follow for bigger guys - carpe_dmg ethandesu thefattorialist thebigsartorialist

From L to R: Carpe_DMG, ethandesu, thefattorialist, thebigsartorialist

Big Guy Style Tip #3: Replace your most frequently worn items first!

As you lose weight, your body shrinks, and you’ll need to replace some things.

Otherwise, if you don’t, you’re wearing clothes that are too big for you! And you won’t look like you lost weight at all.

You want to show off all your hard work, right?

So the big tip here is, as you lose weight, to replace the stuff you wear most frequently, first.

Wear a lot of jeans and flannel day to day? Grab new, smaller, affordable versions of those items.

Drowning in your suits? Time for another trip to the tailor!

A rule of thumb is, for every 10-15 (maybe 20) lbs you lose, you go down one shirt size. Of course, this depends on how big you actually are, but for most guys, this is a good estimation to keep in mind.

So if you’re down 25 lbs, there’s a good chance the clothes that fit decently a few months ago are waaay too big on you now.

So replace them!

You’ll feel your best when your clothes fit right and you look sharp… even if you still have a ways to go in your weight loss journey.

MINI TIP: Find pants with a bit of stretch!

Looking sharp doesn’t have to mean being uncomfortable. Find pants with elastane or some other fabric with stretch property to get max comfort while out and about.

Luckily, many brands make pants with stretch properties in them.

My favorite pair of jeans for guys with bigger legs is the Levi’s 541. I even did a whole video on the 541!

Levi's 541 Athletic Taper Jeans Price: $22+ Levi's 541 Athletic Taper Jeans

To clarify, I’m not telling you to replace everything in your closet just because you’re down a shirt size or two. I’m simply saying to replace the stuff that gets the most wear.

Replacing these items are what will make the most difference in your everyday confidence and look.

Big Guy Style Tip #4: Set milestones and treat yo’self when you hit them

This may sound a bit contradictory to tip #2 (buy affordably), but hear me out.

Going through the process of losing weight is an emotional experience. It takes a lot out of you! It’s a ton of hard work!

And because of this, I suggest setting little milestones for yourself, and once you hit those milestones, treat yourself to something nice.

It could simply be a pair of jeans or a button-up shirt that’s, say, double the price of what you’d normally buy. Or maybe a new pair of sneakers you’ve been eyeing.

For example, I remember when I started my own weight loss journey way back in 2005, I wore a size 38″ in pants and XL shirts.

In fact, the 38″ waist started to feel a bit tight, so sometimes I had to size up to a 40″ waist 😩

I’m not that tall (5’9″) so you can imagine how rotund I was.

So one day, it hit me, and I got really serious about losing weight. I was dropping, on average, 5 lbs every two weeks!

After 2.5 months, I was down 25 lbs and I noticed my jeans were way too loose on me, which made me go 😲 because it was surprising and I guess I hadn’t really paid attention until then.

I hit the mall and tried on some new jeans, and I fit in a size 34! You can bet I treated myself that day.

They weren’t expensive jeans (I think I was at Express Men) but the fact that I was buying a size 34″ was a treat in itself.

Whatever it is, set that goal, hit it, and then do something nice for yourself. You deserve it!

Big Guy Style Tip #5: Keep sizing down until you can’t anymore, then start sizing up

The fact of the matter is, most guys (big, small, short, tall) wear their clothes too big.

And as a big guy, the issue with that is multiplied ten-fold; big, loose clothing makes you look bigger! So you want to size down.

Here’s a little trick to finding the right fit—combine this method with tip #1. Let’s say you normally wear an XXL and you think that’s your size.

  • Next time you’re shopping, find a shirt (or pair of pants, or jacket) you like and take a M, L, XL, and XXL into the fitting room.
  • Start with the XXL, and work your way down.
  • Put each item on and keep sizing down until you literally cannot fasten the pants or button the shirt any more.
  • Maybe you manage to put on the medium shirt but your arms look like sausages and you can’t button it closed in the front. Great.
  • Then, start sizing up again one by one to achieve the best fit.

You might end up at a Large, and that fits great. Perfect!

Or maybe it turns out that XL fits just fine, and you’ve been wearing shirts that are too big.

(Don’t forget to test the fit by sitting down in a chair!)

You never would’ve figured this out if you didn’t try on multiple sizes of the same shirt!

Remember that a well-fitting item of clothing won’t necessarily feel as comfortable as a big, billowy T-shirt or baggy sweatpants. That’s because clothes that fit well are closer to your body. You will feel them on your skin!

So always remember when trying on clothes:

  • Just because you feel the cloth on your skin, doesn’t mean it’s too tight.
  • And just because it’s super comfortable—like your baggy sweats and oversized tees—doesn’t mean it fits well or makes you look good.

Keep in mind: Not all sizes are equal across brands. One brand’s Medium size is another brand’s Large. You have to go through this process with each new brand you try.

That’s why I always suggest when you find a brand or brands that work well for you, stick with them and buy all your clothes there.

Big Guy Style Tip #6 (a bonus!): Thicker and heavier fabrics drape better

Think oxford cloth shirts, twill dress shirts, flannels, etc. These shirts are made with a more substantial fabric and drape—or “lay”—better on your body.

Because of their weight, these shirts have structure and they make you look better because they aren’t hugging every luscious curve of yours.

big guys: how a t shirt should fit!

If you’re wearing a tee by itself, it should fit like this. Perfect sleeve length, shoulder seam hits right where it’s supposed to, and there’s a bit more room in the torso so it’s not hugging every curve of your body

So if you wear a T-shirt under a knit sweater, it’s not as easy to hide the parts you’re looking to hide (and let’s be honest, when you’re overweight, you’re always trying to hide something or make it look a bit less conspicuous).

But let’s say you wear a heavier overshirt or “shacket” over a T-shirt, well, that will do a much better job at complementing your shape and hiding any body insecurities you don’t like.

big guys: how structured clothing gives you shape

This is a good example. The model is wearing a sport coat over a dress shirt. The sport coat has more structure and is designed to give you a waist, making you look slimmer. Whole outfit available at Bonobos

Yes, you can dress sharp, even as a bigger guy

And hopefully this article helps you realize that!

Got any questions? Feel free to reach out to me on social media.

Got a question? Hit me up!

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