Fashion For Big Guys: 5 Tips To Look Great Today (And As You Lose Weight)

by Barron Cuadro  |  in Smart Casual

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 at my heaviest, I was 241 lbs and pushing a 40″ waist (!)

B a long time ago
in my early 20s during the early aughts, 70-80 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
Bonobos Extended Sizes

Bonobos' Extended Sizing: Pants up to a 54" waist; suit jackets will go up to a 54; and tops up to 4XL. There will also be larger belts and ties to complete outfits.

Shop Now

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

When you’re trying clothes on for the first time, sit down! Whatever you’re wearing should be comfortable no matter if you’re sitting or standing.

Pants too tight in the thighs or waist? Shirt pulling apart at the buttons? Sometimes you may not notice these things unless you’re sitting.

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

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

big guys: bonobos extended sizes
Bonobos Extended Sizes

Bonobos' Extended Sizing: Pants up to a 54" waist; suit jackets will go up to a 54; and tops up to 4XL. There will also be larger belts and ties to complete outfits.

Shop Now

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

ASOS: Affordable casual and streetwear looks for big guys

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.

big guys: asos plus sizes for men
Asos Big Guy Sizes

From everyday essentials to standout styles, update your wardrobe with ASOS men's plus-size clothing.


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

Destination XL (DXL)

In addition to carrying their own big guy brands, Destination XL Destination XL (or DXL) also features several major labels like Ralph Lauren, Faherty, and Levi’s. 

So whether you like workwear or preppy styles, DXL is pretty comprehensive. It’s like going to a department store, without having to dig through the back racks, crossing your fingers to find the XL-and-up collection. 

Their own brands focus on comfort and movement, as well as sizes. And, they have loads of suiting.

In fact, they have an exclusive partnership with Brooks Brothers so you’ll get bigger versions of their special fits, like the flattering Regent and close-to-body Milano.

Shop Destination XL (DXL) here →

Large Lad

Large Lad is a family-owned clothing brand based in Canada that’s great for casual pieces and performance wear. They have a wide range of bigger sizes, starting at L and going all the way up to 8XL.

I recommend Large Lad if you want to find stylish athleisure or classic men’s outerwear. They have a nice collection of jackets, parkas, quilted vests, and windbreakers.

They also have some great accessories, like leather belts for the wide-waisted.

If you join their King Club Rewards program, you can earn points per purchase that can be used towards future purchases, which is a nice little customer perk.

Shop Large Lad here →

King Size

With a focus on the tall as well as the large, one of the best parts about the King Size website is that there’s a variety of categories to help you find items you need.

For example, if you hover over Pants & Shorts, you can click on different fabrics, colors, and even occasions. If you hover over Active, you have the option of categorizing based on brands and even features (moisture wicking, shrinkless, and so on).

Shop King Size here →

Big Guy Style Tip #1C: Utilizing Colors and Patterns

Remember, these visual tricks aren’t nearly as important as finding the right fit for your body. However, once you’ve done that, implementing some of these hacks here and there can emphasize the great fit of your clothes and your best features.

First, you can mitigate “problem areas” by wearing darker colors there. Then, try wearing lighter tones to literally highlight features you’re confident about.

So perhaps your thigh and hip area are proportionally bigger, but you have wide, strong shoulders. Go for a lighter shirt and darker pants.

Relatedly, menswear neutrals are your friend, especially for big blocks of color. For example, a pastel pink shirt will draw a lot of attention to the bigness of your frame, while olive green, navy, or gray are generally more flattering.

And finally, vertical lines bring more attention to your longness over your wideness.

This includes shirt patterns, v-neck collars, or even just the buttons that go down the front of your shirt, which creates a consistent visual center and draws attention away from your midsection.

Big Guy Style Tip #2: Follow Big Guys Who Dress Sharp On Instagram and TikTok

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.

And of course, TikTok has plenty of fashion influencers you can follow that emulate different kinds of style, from trendy to essential and classic.

Check out our guide to some really cool TikTok fashion influencers.

Some include Nick Urteaga (Coastal Flicks), who offers great outfit inspo and brand shout-outs, Darijan (Yetti.rice), who has an excellent understanding of his frame and proportions, and DapperDom, for easy casual looks.

Big Guy Style Tip #3: 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
Some well-publicized transformations from Zach Galifankis and John Goodman

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

fat to skinny celeb transformations seth rogen adam richman
Weight and style transformations by Adam Richman and Seth Rogen

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.

Big Guy Style Tip #4: 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!
  • Are your shoes suddenly looser? I went from a size 10 to a size 9 after losing 80 lbs… yes, your feet lose weight, too

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.

Also worth the read: Yes, You Can Dress Stylishly As A Larger Man – Here’s How (via Mr. Porter)

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.

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 #5: 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.

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 built in. My favorite pair of jeans for guys with bigger legs is the Levi’s 541 Athletic Taper. I even filmed an entire video on the 541!

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!

BONUS Big Guy Style Tip #6: 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!)

testing how your shirt fits while sitting down

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.

BONUS Big Guy Style Tip #7: 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!
These shirts are from Asos

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
All these clothes are from Bonobos

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.

You can pull off this classic look super easily! I believe in you.

If I were you, I’d start by checking out Bonobos’ extended sizes below. Not only should they have something that fits you, they also have a generous return and exchange policy, so you won’t be stuck with stuff that doesn’t fit.

Bonobos Extended Sizes

Bonobos' Extended Sizing: Pants up to a 54" waist; suit jackets will go up to a 54; and tops up to 4XL. There will also be larger belts and ties to complete outfits.

Shop Now

Now, if you’re in a situation in which you have to wear lighter fabrics, say it’s just way too hot out, it’s all about the drape. Again, a heavier cotton t-shirt will drape better than a thinly-woven one.

However, if you can find a lightly-woven shirt that has great structure around the shoulders, that allows the silhouette to hang more cleanly. A linen button-down is a good example.

Basically, you want pieces that still have a clean shape and won’t highlight lumps and bumps.

A silk twill collared shirt is another good example, and can even be layered with a linen blazer for smart casual situations. The shirt is light but sturdy, while the blazer contains your sides with straight, strong lines.

Top 5 Essentials for Any Big Guy’s Wardrobe

Here are a few pieces to level up any lean rotation:

1. A short-sleeve button-down

Instead of a regular crew-neck t-shirt, go for a cotton button-down that creates a visual center and provides architecture around your shoulders.

Nautica Oxford Sport Shirt

"Made from a soft stretch​ cotton blend, this short-sleeve shirt ​from Nautica belongs in every guy's weekday lineup."

Shop DXL

This Nautica shirt from DXL is also made with elastane which means it’s as easy to move in as a less firmly-built t-shirt.

2. Stretch chinos

Chinos are a menswear essential, but are especially flattering on bigger guys because they bring straight-structured lines to casual pants. Stretch chinos are practical everyday wear and can be dressed up or down.

Bonobos Extended Sizes

Bonobos' Extended Sizing: Pants up to a 54" waist; suit jackets will go up to a 54; and tops up to 4XL. There will also be larger belts and ties to complete outfits.

Shop Now

We’ve mentioned Bonobos’ Extended Sizes a bit earlier in this post, but that’s where I’d suggest looking at stretch chinos. That’s basically their bread and butter, so you know they have tons of variety.

3. V-neck cardigan

Whether you go for a lightweight jersey or a fleece, a cardigan is an excellent complementary layer.

Polo Ralph Lauren V-Neck Fleece Cardigan

"This cotton-blend V-neck sweater from Polo Ralph Lauren ​combines the polished look of a cardigan with the warmth of a signature Ralph Lauren fleece."

Shop DXL

In addition to the slimming effect of the buttons and the v-neck, you can wear it over a patterned shirt and under a suit jacket to create three smaller sections on your body compared to one giant color or pattern block.

4. At least two perfectly-fitted suits

Again, going for the perfect fit will make all the difference.

The reason I say two suits is, if the dress code allows, try and go for a broken suit over a full suit, with darker pants and a lighter jacket.

For example, a charcoal jacket with dark navy pants, or a navy jacket with black pants.

For this, again I suggest browsing Bonobos’ offering here.

5. A well-structured coat

A properly-architectured jacket made with the right materials can be really flattering.

Remy Leather Trim Wool Coat

"Professional enough for work and stylish enough for a night out, this beautifully designed coat in a luxurious​ wool/​cashmere blend will keep you warm in style for​ years to come."

Shop DXL

This Remy jacket is a luxurious cashmere and wool blend, meaning it drapes strongly but not stiffly.

The leather accents are also nice touches, making it elegant enough for dressier occasions while unstuffy enough to level up casual outfits.

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

And hopefully this article helps you realize that!

If you have any questions or comments, DM me on Instagram!

What’s changed?
02/22/2024Updates to text, added video embeds, updated links
12/04/2012Original publish date