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.
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 (!)
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?
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
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
For example: With woven
From there, how far away can you pull your
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.
MINI TIP: Sit down in the fitting room when trying on clothes
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
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.
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.
Keep in mind, this is more trend-forward stuff, but if that’s your jam, I’d start looking here.
Big Guy Style Tip #2: 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.
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.
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.
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
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
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
MINI TIP: Find pants with a bit of stretch!
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
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 #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
- Maybe you manage to put on the medium
shirtbut 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
(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
MINI TIP: Go shopping in the afternoon or evening for the BEST fit
Remember that a well-fitting item of clothing won’t necessarily feel as comfortable as a big, billowy T-
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 #7 (a bonus!): Thicker and heavier fabrics drape better
Think oxford cloth
Because of their weight, these
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-
But let’s say you wear a heavier overshirt or “shacket” over a T-
This is a good example. The model is wearing a sport coat over a dress
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.
Yes, you can dress sharp, even as a bigger guy
And hopefully this article helps you realize that!