A couple of years ago, I bought a vest from a stall at Barras. It was genuine vintage weave style stuff; proper old school ribbed cotton. I should have realised when the guy insisted I was buying a large because there were big guys in Scotland in the 70s, you know? But I didn’t and it fitted like a damp apology. If your sleeves ended at your elbows AND you somehow had less muscle definition you could maybe get away with it. Pinched at the neck after a week.
Baggy at the waist after two.

Didn’t survive three washes before it was something to clean a bike chain with. And yes, eventually I used it for that exact purpose.
The thing about vest sizing that no one tells you is that the label isn’t exact. It’s a rough guide someone made up once and everyone’s been using as atemplate ever since.
So working out your actual vest size is all down to two details people consistently get wrong, and consistently wrong. How to measure yourself for a vest, which everyone thinks they know but mostly don’t. And how it fits once it’s actually on you and doing what vests should; covering your upper half while you move, sweat, and live. Rather than just sitting flat on your bed looking like a thing that won’t give you grief.
Chest measurements aren’t as straightforward as you’d think
I thought I knew my vest size forever because once upon a time I bought a shirt and saw what it said down the back. Stuck with me like Some Gospel. Except it doesn’t work like that, I learned the hard way by buying three exact same vests, only to discover ONE FITS ME WHILE THE OTHERS ARE LIKE I STUCK WHEELS ON AN AGED GILBERT SOLOMON
Different brands cut their vests differently, even when the label is screaming the same size at you. You need to measure under the arms, across the biggest part of your chest, tight enough to get a number but not so tight you start cutting off circulation. And writing that number down, because trust me when I say you’ll forget it if you rely on memory alone.
The worst bit is that your vest chest size isn’t the same as your shirt size. Sounds like it should be but it’s not. Shirts have structural bits like buttons and collar giving it shape vests can only assume you’ve got there with footwear alone. Vest fit is 90% about the fabric stretching how it’s meant to and the cut of the armhole. My mate’s been buying vests one size larger than his shirt size since he was twelve, swears it’s the only way he gets them to fit right. So naturally, after knowing him for years I’ve started copying him.
The other mistake is what happened to me at Barras. Think of vest as two different eras wear the same name. Old school cotton, and I mean old like your grandad’s wedding shirt, were cut slimmer through the body. As they were designed to wear under a shirt, not actually show. Everything from the big brands up these last ten to fifteen years has been wider cut to actually be seen as a viable clothing layer. Gym to pub kind of thing.
Want a vintage find that fits? Go slim on the sizing if the labelZ actually say vintage. Not something some poor mark had to haggle on in a factory shit sell last summer. You’ll know the real stuff when you see it, trust me. Check the label, check the stitching. Real cotton from the good old days doesn’t have that fuzzy fake worn look ironed onto it.
How it fits when it’s actually on you is more important than any number
This is going to sound so dumb but hear me out. That chest measurement you just took can be spot on and it still won’t fit correctly when you move around. The reason is that measurements only tell you about a vest that’s flat on your bed and staying fucking still. You won’t spend all day Saturday sat or standing still wearing a vest, trust me I sell enough of them to know. Armholes are where most vests fall down, not the chest. Tight enough and it’ll rub your every time you raise your arm. High chances you’ll be doing that if you wear vests with jackets, which is pretty much all day if you got married last year. Too loose and it creates gaps that showcase your side you probably don’t want to.
Necklines matter too. High and it’s uncomfortable by mid afternoon, come away is so low it basically turns your vest into a top that’s trying too hard. Look at cool but I’m yet to meet someone who rocks that look intentionally.
The real test is wearing it around for longer than you think is necessary. Go home, put it with some jeans you like, then spend a whole day wearing it around doing chores. Reach for a plate off a shelf, then look in the mirror. Nothing teaches you fit better than your own bod. Bend down to tie your shoelaces. If it rides up past your belt either sitting or bending then it’s too small, full stop. No clever way to explain that away later.
Don’t get me started on the fabric verses sizing conundrum. Pure cotton, or close enough to it, will always need a slight bump on size to account for ZERO stretch. Stays put whether you like it or not.

Vest with elastane?
Luck, depending on how much they will give that number you just took above. My drawer is split fifty fifty now Vest jams? Buy a bigger size. It’s happened to all of us.
The moral is work it out yourself. Get your measurements right, then wear the stupid thing before you decide. Put it on, move around, make sure it feels good WHILE you’re doing. That shouldn’t take long. That’s honestly my whole vest sizing rant.