I received a text at exactly 10: 47PM that said: “Hey I need your help! I’m meeting Sarah’s parents tomorrow and I have nothing to wear. How can I make my boring clothes not look boring? ?”.
Marcus. My perennially-underdressed friend with the uncanny ability to continue dating stylish girls despite this glaring flaw. Attached was a mirror selfie of him wearing, without exaggeration, the most aggressively bland outfit ever sent to me via text message.
Navy blue crew neck jumper, plain jeans, white trainers. Not bad dude, not great, just exists ings. “Half tuck your jumper.
Roll up your sleeves to show your watch.
And for fucks sake iron it”, I replied. “ cuff your jeans once. Once people. Not twice.
And stop taking selfies in front of a dirty mirror. It looks like a crime scene.” An hour later I received a new photo from Marcus. Same exact jumper.
Same exact jeans. Same exact trainers. But put together in such a way that he now looked like he belonged on the cover of a magazine titled Everyday Menswear For Men Who Hate Dressing Up.
He aced his meeting with Sarah’s parents. She still loves him. And every time he gets ready to go somewhere where he wants to look “nice” he still texts me for advice.
Moral of the story? Clothes don’t make the boring outfit. How you wear them do.
Trust me when I say I’ve spent way too much time dissecting what it is about certain Instagram outfits that make them look SO damn good despite being made up of pieces most guys already own. I’ve worked in the fashion industry long enough to know every trick a stylist uses to make clients look amazing on camera. And I’ve scrolled through enough Instagram that I know every trick the coolest guys on there are using to build THAT insane aesthetic I’m jealous of.
Now I’m gonna teach you how to use those tricks to actually look good IRL. First up, let’s talk about the most basic, and often overlooked aspect of any truly Instagram-worthy outfit: fit. Fit doesn’t just mean “does it fit you” but HOW it fits you.
Most guys’ clothes are too big or too small in all the wrong places. But any outfit you see on Instagram will be fitted perfectly. Not too slim, not too loose, just how a well tailored piece of clothing should sit on your body.
The sleeve will hit directly at the base of your wrist. The shirt will be loose enough that it doesn’t cling and look like a smoking shirt, but not so loose that it looks like a house dress. Your trousers will hit directly once on your shoe.
I didn’t used to understand this concept when I was first learning how to dress better. I thought as long as I was buying slim fitting clothes I was good. UNTIL I took photos of myself and noticed how awful I looked.
My jeans would pile up at my ankles. My shirts would have shoulders that went beyond my actual shoulder. My sleeves would cover half my hands.
I looked like a toddler dressing up in their parents clothes. It wasn’t until I started doing my own shopping that I realised I actually went down a size at most of my brands. Not because I lost weight, oh no I gained an entire pound since writing my last article.
But because I FINALLY understood how my clothes were supposed to fit me. Which brings me to my next tip: intentional imperfection. Look at any half decent Instagram outfit and I can almost guarantee it has one “casual” element.
The half tucked shirt (also known as the french tuck, shoutout to Tan France), the rolled up sleeve, the slightly unbuttoned shirt. These subtle details tell your audience you know what you’re doing, as opposed to throwing on a shirt and hoping it covers your butt. I actually made my shirt dresser for photoshoots, David, purposely unknot shirts I went out of my way to properly iron. “It looks too perfect”, he’d say. “No one actually walks around that crisp.” He didn’t button the top button on dress shirts, he purposefully rolled up my sleeves unevenly, and tucked my shirt out slightly on one side.
The photos turned out 10x better because my “trying too hard” vibes were washed away and replaced with something that looked natural. Speaking of shirts, my next styling tip is all about proportions. Proportions of the clothing pieces themselves, but also how they fit together.
Any shirt you see on an Instagram guy will always have an element that is purposely NOT fitted. They’ll wear slim jeans with an oversized jumper. A fitted t-shirt with boyfriend jeans.
A fitted blazer with baggier trousers. This technique is what makes basic combinations look anything but basic. I used to think my go-to out should was perfection. “SLEEVES MUST FIT”, I’d say. “TROUSERS MUST BREAK ONCE.” I looked almost robotic in my outfits.
It wasn’t until I started mixing my slim jeans with slightly more boxy shirts, or wore my fitted button ups with relaxed trousers that I suddenly looked stylish while wearing the same exact clothes I had for years. Same goes for colour matching. Rather than trying to match colours exactly, try dressing within the same colour palette.
Stick to 2-3 colours that complement eachother. It’s rare you’ll see a well dressed guy on Instagram with more than 3 colours on. And 9 times out of 10 those colours all come from the same colour family.
Like I said earlier, I stumbled upon this when I couldn’t be bothered to do laundry one month in my twenties. I literally ended up wearing only blues and greys for like two weeks. Not only did my outfits strangely match, it was better than my old “wear something red for a pop of colour” mentality.
Something about matching tones just looks extremely put together. Ok time for the big one. The most important accessory you’ll wear is confidence.
Want to look good in your clothes? Act like you have a reason to be wearing them. Every single photoshoot I’ve ever done, the stylist will say some variation of “look natural, you’re not posing.” “Act like we’re not here.”“ Do whatever you’d normally do.” Photos of people who look awkward in their clothes are automatically deleted no matter how good the outfit actually is.
It’s instilled in us as humans to trust and follow confident people, and if you don’t exude that confidence while wearing an outfit, you’ll never master the art of looking good in it. I watched my amazingly handsome roommate, Trevor, walk into a wedding wearing 1 of 7 men that were wearing the exact same suit as me. But he looked 100x better than anyone else in that room.
When I asked him what his secret was he looked at me bewildered. “ Dude I just like how I look in this suit.” He walked with better posture. His hands were relaxed. He carried himself differently than I did wearing the same exact clothes.
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If you don’t actually like what you’re wearing, nobody else will either. Now for some tricks you see on Instagram that just don’t work IRL. DRAPES DON’T WEAR, THEY JUMP.
Okay maybe that’s a bit dramatic. But you know what I’m talking about. The coat thats sitting on the models shoulders and isn’t actually being worn.
Looks great on Instagram. Looks like a HUGE target for jockeys when you’re trying to walk through Times Square. I once draped my jacket over my shoulders at a fashion week show and had it autumn off within 3 minutes.
Knocking over the girlfriend of a very angry Italian guy and his drink all over himself. I had to workout of the crowd to fish it out of the feet of passing strangers while they screamed at me in Italian. Wear your damn jackets people, like garments intended.
SHIRT STYLING CLIPS. What looks like a perfectly fitted shirt on Instagram is actually most likely being clipped to the models back to give the illusion of a good fit. Makes sense why no one can replicate that exact “fits like a glove” vibe.
Unless you want someone constantly following you around and tugging at your shirt from behind you, this styling trick is pretty impossible to recreate. (Hint: Get your clothes tailored instead) Ok now for some real tips when it comes to dressing better IRL: Accessorize. Listen whatever your stance is on men wearing watches I stand firmly in the middle. Watches are cool and all, but they’re only the START of men’s accessories.
One of my favourite things to notice about guys on Instagram is the small details they include that are NON clothing related. Awesome sunglasses. Cool belts.
Sick trainers. But most importantly: personality. Whether it’s a pair of bracelets with vintage band tours hanging from your wrist that have actual significance or a necklace from your grandparents or a nice pocket watch.
Find one cool accessory to include with your outfit that isn’t a watch. As someone who used to think that was the end all be all of men’s accessories I didn’t understand this until way too later in life. I didn’t start getting interested in accessories until I bought a pair of vintage Wayfarers with scratchy lenses that actually changed how I approached my style.
The sunglasses were so comfortable and vintage looking I actually wore them everywhere. It wasn’t until that point that I started exploring more into slightly sexy socks, bracelets with meaning, or a cool watch to finish off an outfit. You don’t have to go full Blunt Force Jewellery with jewellery on every finger.
But one cool extra accessory can go a long way. All of my favourite Instagram outfits tell a story. Where are you going?
What do you plan on doing? Who are you wearing to? Any cool outfit will instantly give you some sort of answer when asking these questions.
And if you have no clue, pretend you’re going to a cool boyscout jamboree or something. The point is your outfit should match the imaginary story you’re going out to accomplish. Exhibit A: my friend Eric’s go to outfit for dates.
Dark wash jeans, olive green button up, desert boots, and a leather watch his grandpa gave him. Everything about this outfit fits the “story” he’s telling which is pretty simple: “I don’t want to wear a suit but I’m also not trying to fuck around.” His shirt is ironed enough to be tidy, but not stiff. His jeans are cleaned and broke correctly but not nearly enough that he cares if they get stained.
His boots are desert boots because he wants to. And that watch he got from his grandpa gives off hints that he comes from a family with actual style. But it’s not so flash-y that he’s trying too hard.
It’s a complete outfit with a complete vision, rather than a bunch of random things thrown together. Include a “third piece”. This one may take some explaining.
When most of us think of an outfit we think of two pieces: a top, and a bottom. But your outfit doesn’t end there. Add something on top of that.
Whether it be an unstructured blazer, a linen overshirt, a denim jacket, or even a nice belt to include as a “third piece” to your outfit and you’ve gone from wearing “clothes” to wearing an outfit. It’s why you see so many guys layer on style Instagram. It instantly takes a basic combination and makes it look more put together.
Here’s another great example from Eric. We were going to a casual dinner and knew we were dressing too similarly to “match” so we both added a third piece to differentiate ourselves. Same exact shirt, trainers, and jeans.
But add something on top to instantly elevate your outfit. The last tip that will 100% help you look better in your clothes: Maintenance. How are your clothes washed?
How are your clothes hung? Are your shoes rubbed? How’s your haircut?
These are all things I inquire when helping a new client. Because yes, your clothes DO make a difference in how you look in your clothes. And when you take as good of care of them as you do picking them, everything else becomes that much easier.
One of my favourite jackets I own still looks bad in photos to this day.
Not because of the jacket, but because I didn’t realise how wrinkled it looked when I unboxed it. I didn’t bother steaming it out before wearing it for photos.
And at the time I hadn’t got my hair cut in months. Didn’t realise how UNtil I fixed those 2 things, my once favourite jacket still looked like crap in photos. Steam your clothes if you have to, keep your hair trimmed, take care of your clothes.
You’ll be surprised how much of a difference it makes. Ok guys that should do it. My biggest tips for taking your boring outfit game to an Instgram worthy level.
Don’t forget: –Fit is everything -Add an intentional flaw -Mix Slim with baggy -Stick to a colour palette -Find one cool accessory -Tell a story -Convince yourself you’re wearing this outfit to the cool boyscout convention -Add a “third piece” -Take care of your damn clothes. Oh and once I told Marcus all of these tips. He sent me this photo.
Lesson learned, don’t be like Marcus.
