Growing up I never paid for clothes to be tailored. In fact, I didn’t even know you could tailor regular clothes. Tailoring was something people did for crazy-expensive suits or wedding dresses.
Clothes should fit off the rack shouldn’t they? Wrong. Let me explain.
One day I learned how. I was shopping with my friend Mike and watched him transform right in front of my eyes.

We went from baggy sweatshirt style shirts and trousers that dragged on the ground to custom-looking clothing after dropping $87 at his tailor shop.
I couldn’t believe how much of a difference it made. Some guys can spend $20 on a shirt and look like they spent $200. How?
Most guys don’t have the body frame that stores use to stock clothes. Mike is six-foot-four, has actual shoulder muscles (unlike me) and legs-for-days. Whenever he walked into any store there were only 2 options: trousers and shirts that were too short or ones that fit in his waist but hung off his body everywhere else. “I’ll just wear the trousers.” he laughed while we were shopping for his sisters wedding.
We spent our entire Saturday at Nordstrom letting him try on suit after suit. Jackets would either fit perfectly in his chest, but be cropped in his arms. Or they would cover everything and make him look 3 sizes too big. “I’ll just wear the trousers.” Mike said. “Yeah no shit, that’s not happening.” I replied.
I wasn’t about to spend $900 on a suit that didn’t fit him perfectly, but there had to be something we could do. We found a suit that fit him perfectly in the shoulders (Tailor Park told me that’s the most important place to fit because you can’t have your shoulders altered) and Mike stood on a box while we pinned the rest. Mr.
Park walked around him eyeing every angle, marking where his trousers fell, took in his waist, and shortened sleeves. He was like Navy seal with a needle and thread. When Mike put that jacket back on two weeks later his face said it all. “Holy shit, I have a waist!” The jacket actually fit his torso instead of looking like a big grandma coat.
His trousers hit his dress shoes perfectly instead of bunching around his ankles. His sleeves weren’t too long, giving just the right amount of shirt cuff. It was a completely different suit. [youtube https: //www.youtube.com/watch?v=RZa9ADYjbN8] We ended up buying that jacket and he went to his sisters wedding wearing it.
His sister-in-law even pulled me aside at one point to ask me about it. “What happened to Mike? He looks… intentional.” If that isn’t the best compliment to make you realise tailoring isn’t luxury, I don’t know what is. My grandpa got it.
He was a butcher his whole life. He didn’t make much money, but could walk into a bar wearing a tee and jeans and look better than most guys spending 10 times what him. He knew that just going to a store and picking out clothes was only step 1.
Having them actually fit you was step number two. Why has everyone else forgotten this step? Growing up I knew no other guys that had their clothes tailored.
It’s like most guys my age just accept that “if a shirt or pair of trousers don’t fit… you move on.” But that logic doesn’t make sense once you see how clothes are supposed to fit. They are designed with the “average person” in mind. Someone who has no shoulder muscles and the waist of Chris Bosh.
Models even have their clothes tailored before they step on set for photo shoots. The idea that anything should fit you perfect off the rack is laughable. I didn’t know this until I was way older and frustrated shopping for clothes that didn’t fit me.
I’d ask myself why I always looked sloppy compared to other guys. Then it hit me, they weren’t necessarily buying better clothes. They were just getting them tailored.
SO WHAT SHOULD YOU GET TAILORED? I learned the hard way by trying everything and spending way too much money. I ruined that vintage leather jacket I mentioned before by having it “slimmed” in college.
But I learned what alterations changed everything and what you shouldn’t waste your money on. Lets start with shirts. Shirts are the most important item of clothing to get tailored.
Why? Because they’re on you every day. Standard men’s shirts are cut straight down from the shoulders.
This creates a huge flap of fabric when you tuck it in. It makes you look like a floating pasta boat wearing a shirt. Mr.
Park calls it “the reverse muffin top” and hates when guys don’t get this done. For about $20 they’ll take the excess fabric from the sides and create these 2 little darted lines in the back that make your shirt actually fit your body. I get every dress shirt I own darted in the back.
Hell my girlfriend was the first person to notice when I started doing it. “Wow your shirts actually fit you.” YOU LIVE UNDER A ROCK IF YOU DON’T GET THIS DONE. Sleeves are also important on shirts. Most guy’s sleeves are too long.
It creates bad proportions and adds to that overall sloppy look, especially when you wear jackets with them. Hemming those suckers up will make all your shirts look 10x better. I learned this tip on jeans when I started getting my pant legs tailored.
Every guy thinks they need to hem their jeans to match their shoes. They don’t. Jeans should hit your shoe whatever the hell you want them to.
Get them hemmed to your desired length. Same goes for altering the rise if your trousers are gaping at your back waist. You know how your trousers always kinda autumn down a little and you’re constantly tightening them?
FIX THAT. Along with hemming, this was the best change I started making. My trousers actually stayed up!
Another big one is taking the legs in on trousers that are too baggy at your ankles. These were my dads dress trousers he found in his donation pile. Too ‘90s dad fit on him so he was about to toss them.
I took them to Mr. Park and had him taper the legs. $25 later I had the nicest pair of dress trousers that I wore all summer. I could talk about trousers all day but lets talk about jackets.
Jackets and blazers are where tailoring can really make your clothes look expensive. I won’t lie to you, if the shoulders don’t fit on a jacket there is no fixing it. Other than that you can alter every other thing about a jacket to your liking.
Pretty much all the same rules for shirts apply to jackets. Get those sleeves hemmed so they end about ¼ inch above your shirt cuff. It drives me crazy how many guys get this wrong.
Taking in the waist on a jacket is my favourite alteration. A jacket that fits your waist looks like it’s custom tailored. I found this blazer at a thrift store in Boston.
Awesome looking italian wool, but way too big everywhere on me. $75 in alterations later (shortened sleeves, took in waist, fixed buttons) I had a $600 looking blazer that cost me $115. Will this work with everything? Of course not.
Don’t spend more on tailoring something than the jacket is worth. Unless it’s something you love and will wear often. Also, don’t go to your local dry cleaners to get something tailored.
The people that just do alterations at the dry cleaners down the street don’t know how to properly reconstruct a garment like Mr. Park. Speaking of Mr.
Park, lets talk about your tailor. I had to try about 4 different tailors until I found Mr. Park and I swear by him.
He looks like your grandfather that works at the hardware store in the back of his shop. He doesn’t even have a real “waiting room”, just 2 fold up chairs. But guys bring him clothes that are straight from Designers!
What Mr. Park taught me was how to spot a good tailor. Step 1: Try them out with something small.
See if they ask you how you wear your shirts. Do you wear dress shoes or trainers with them? Do you like break on your trousers?
Good tailors aren’t going to just do what you want, they are going to give you their professional opinion on what looks best. Also, my tailor doesn’t sugar coat me. He sat across from me, chewed me out if he caught me wearing dirty clothes to his shop, and still sends me my clothes right away when I drop them off.
All of his customers are guys that have been with him for years that he “trusts” with his life work. He once told me I should just start handing random clothes out to his customers because he knows they will do a good job. Trust me I know it sounds weird, but once you start building that relationship with a tailor you’ll understand.
Instead of throwing away clothes that don’t fit you perfectly, you can alter them to fit your body. That oversized pullover Oxford that was too big everywhere? $25 to tailor, now my favourite shirt. Want jeans that look & feel like they were made specifically for you?
Get the thighs slimmed out! Shopping will change when you start tailoring clothes. That sales section in your favourite store?
GOLD MINE when you know you can tailor things to fit you. Huge discount on that designer jacket because it’s size large and comes down too far in the torso? Buy it if the shoulders fit!
You can tailor the rest. I see guys walk past clothes they would look great in all the time just because they need altered. We’ve been brainwashed to think clothing should fit when we buy it, but that’s not true.
Challenge yourself to go through your closet and find something that doesn’t fit you that you love. Maybe it’s a shirt that’s too boxy around your torso. Maybe it’s trousers that are too long in the legs.
Something small, spend $20-$30 to have it tailored and watch that become your favourite item you own.

When Mr. Park retired last year he sat me down and told me, “Kids these days don’t understand clothes.
They buy em, toss em, buy more. But you Jordan, you get it. You bring all your friends over.
Let them learn. This is good.”. I think he’s onto something.
If every guy started tailoring their clothes instead of complaining there’s not stuff that fits off the rack we could all look better. Don’t take my word for it. Go buy one thing and get it tailored.
You’ll become that guy.



