I remember it like it was yesterday. I was leaving to grab dinner with my then-girlfriend’s father when he gave me what was, up until that point in my life, the worst style critique of all time. I want to be very clear here – this was not the downtown chic type of critique where Patrick from accounting breaks down your thrift store ensemble using ultra fancy words you don’t understand.
This came from my girlfriend’s dad, a dentist from the Midwest who probably spoke twelve words a day if he was really pushing it. So when he gave me his assessment before we left the house, I listened: “You clothes are nice. But they don’t fit you.” There are few things more soul crushing than realising the man with zero interest in clothes obviously sees right through your carefully crafted self-image as a stylish dude.
And worst of all? He was totally right.
Sure, the clothes I was wearing weren’t horrible – I was wearing some solid jeans, a decent button-down, and nice enough shoes – but they just didn’t fit.
My jeans were too long and rested awkwardly in bunches above my shoes. My shirt was stretched too tall and too wide and made me look like I stole it from my brother. Nothing was “wrong” per se with my outfit that night, but nothing was “right” either.
There were a few moments in my life that made me really start to think about clothes and how we wear them. That was one of them. It occurred to me sitting there while he fixed my shirt that most dudes aren’t poorly dressed because they don’t have nice things.
They’re poorly dressed because they don’t wear the nice things they own correctly. The guys I’ve met who dress the best; money has absolutely nothing to do with it. What they do have in common are little tricks; small adjustments they make that cost absolutely nothing but can mean the difference between looking put together and looking… well, not.
If you spend any amount of time reading/style tweeting with me, you know I typically write about clothes ranging from affordable to pretty damn expensive. But today, I wanted to shine a light on style adjustments that won’t cost you a penny. Whether you rock a $5,000 Italian suit or got your clothes at the local thrift store, these styling techniques can help you improve your look from head-to-toe.
Let’s dive in. The most important zero-dollar style adjustment there is? Getting your pant length right.
There’s nothing that looks more “I don’t know what I’m doing” than trousers that bunch too high around your ankles or show off 3 inches of your sock when you’re standing. The right length? They should hit slightly above your shoe and create a small horizontal crease as they break over your shoe.
But they shouldn’t stack up like a puff pastry. If your trousers are too long – and let’s face it, most guys’ trousers are in America – you have a few free options: Pinrolling is the chic way of tucking your trousers inside your shoes. To do it right, fold your trousers inside along the original pant seam, then make a small roll up toward your ankle.
It should take about 15 seconds and looks great with everything jean or casual chino related. If you’re rocking dress trousers, the timeless military tuck remains the king. Simply fold the excess fabric toward the back of your leg and create a new crease along your existing trouser crease.
Then buckle down with your belt and let that belt tension keep everything looksput together.quiteIn south properly tucked at the waist. Speaking of tucked shirts, not all tucks are created equal. There are tons of instances where you shouldn’t fully tuck in your shirt, but when you do decide to tuck, do it right.
Tucking your shirt all the way in is formal. Leaving it excessively untucked looks sloppy. The solution is something I like to call the strategic or partial front-tuck, aka the “French tuck.” Tuck the front half of your shirt into your trousers, but leave the sides and back untucked.
It creates intention and looks great with everything from t-shirts to button-downs. The key is to make it look effortless rather than calculated – taking no more than two seconds. We’re big on shirtsleeve rolling around these parts, but not all rolls are created equal.
Let’s say you’re wearing a long-sleeve shirt and want to roll up your sleeves. Instead of lazily pushing them up and calling it a day, take 15 seconds to create a nice forearm roll. To do this, unbutton your cuff and flip your sleeve all the way back once, then roll your sleeve up 2-3 times until your cuff ends just below your elbow.
It looks intentional instead of sloppy and actually stays put all day. Same rules apply if you’re wearing a t-shirt or polo. Take your thumb and index finger and pinch the bottom edge of your shirt about half an inch.
Fold that excess fabric underneath itself. It creates a much more tailored sleeve and prevents shirts from ballooning out at the bottom if you’re a skinny-arm kind of guy. One of my favourite money-free style adjustments is called the contrast shift.
Contrast, put very simply, is how dark or light your clothes are relative to each other. Most guys wear high contrast clothing combos (dark jeans, light shirt) regardless of their colouring. But by dressing in lower or higher contrast depending on your features, you can instantly look more put together.
Light features (light hair and light eyes) look better wearing low contrast colour combinations (navy jeans + white shirt is high contrast, khakis and light blue shirt is considered low). Darker featured guys have higher contrast colouring and can generally get away with darker vs lighter combos. It costs literally nothing to adjust, you simply need to pay attention to which colours you’re pairing together.
Underrated AF money free tip: unbutton your shirts. I can’t tell you how many times I see dudes button their shirts all the way up or completely off. There’s an elegant medium that frames your body and face better.
With casual shirts, leave the top two buttons undone. With dress shirts and jackets, leave the top button undone. It makes all the difference.
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Another personal favourite tip is what I call the rule of asymmetry. Asymmetrical things are more visually interesting and appear more put together than symmetrical ones. You can implement this philosophy with your wardrobe in almost any scenario: leave one side of your shirt untucked while tucking the other side, roll one sleeve slightly higher than the other, push up one side of your collar.
These tiny differences may not seem like much on their own, but our brains register that asymmetry and deem it intentional. Another crazy effective tip? Good old posture.
There truly is nothing – nothing – that will make you look more or less expensive than how you hold yourself. I don’t care if you’re wearing a $2,000 bespoke suit or something you threw on from Costco. If you have rounded shoulders and slump forward, it’s not going to look good.
Stand up straight, shoulders back and down, chest forward, feet shoulder width apart, and chin parallel to the ground. Do this for a couple minutes every day until it becomes habit, and instantly every item of clothing you own will look better. Take your pocket game to the next level and you’ll look more stylish in the process.
Stop stuffing your front pockets with everything you own. Not only will it make your trousers look bad, but it just looks sloppy. Try the following pocket hacks to look instantly sharper: Only wear one thing in your breast pocket.
Sunglasses work nicely or try this trick with a pocket square. Keep your wallet in your back pocket or even your jacket pocket to eliminate that dreaded “pocket tumour” look. If you’re wearing a watch, pay attention to how it’s sitting on your wrist.
Is it just flopping around or are you wearing it properly? The right way? On your wrist bone.
Snug but not too tight. Practise this with your $50 watch from Target and you’ll look instantly more put together. With suits and sport coats, one of my favourite free style adjustments is how many buttons you’re wearing.
Traditionally, we’re taught that jackets with two buttons follow the “sometimes, always, never” rule. Sometimes button top button while standing. Always leave the bottom button off.
Never button your jacket while sitting down. But you can take this one step further. If you want to look slightly more casual, leave your jacket completely unbuttoned.
Conversely, if you want to look instantly sharper, button it up. It costs nothing to try this trick and can completely change how your jacket fits your body. Tilt your belt buckle away from centre and you’ll look sloppy.
I know, I know, who cares about belt buckles being perfectly centred? Well. You should care.
Spend 2 seconds aligning your belt buckle with your trousers and people will think you spent more time (and money) getting dressed. Speaking of tiny details, pay attention to your tie knot. Not only should you have a nice dimple below your knot, but that knot should be centred on your waistline.
Both of these things are simple adjustments that require no money but will elevate your shirt and tie game. Another trick I love is colour echoing. What this means is making sure at least one colour is repeated throughout your outfit in multiple places.
Maybe that watch strap is the same colour as your shirt. Perhaps your socks are the same colour family as your pocket square. It doesn’t matter how or where – you just want to make sure multiple pieces are touching colours.
It creates visual harmony and will make your outfits look more intentional. Same rule applies when dressing casually. Throw a jacket, shirt, and pair of trousers on and you look kinda blah.
But add something “extra” and it instantly elevates your outfit. Call it the third piece rule. It can be as simple as unbuttoning a lightweight jumper and throwing it over your shoulders or tying a bandana in your breast pocket.
It adds detail and style to an otherwise plain outfit. Buy clothes that fit. It can’t be said enough.
Americans wear way too big of clothes.
But that doesn’t mean the stuff hanging in your closet that’s too big should be worn all the time. Identify the clothes that fit you best and wear those throughout the week.
Save the baggy stuff for Sunday hangovers and weekends. There’s a reason we put this tip first. Styling tricks only get you so far if your trousers aren’t the right length or your sleeves are halfway rolled up.
These zero-dollar moves are great, but only if you’re starting off with clothes that fit relatively well to begin with. As you implement these tips, take note of which ones you like and which ones you don’t. Find out what works for you and your style.
And most importantly: have fun with it. You’ll look better tomorrow than you did today. I promise.
