It was 10:47 PM. The text read, “OMG HELP! Meeting my girlfriend Sarah’s parents tomorrow and need tips on making my boring-ass clothes not look boring.” It was from Marcus, my closet fashionable friend who is always underdressed but continues to date the coolest girls.
He sent along a mirror selfie wearing what I’ll generously describe as a “functional” outfit. Navy blue crew neck sweater, basic jeans, white sneakers. Nothing special about it.
But also not ugly or inappropriate. Just there. “Half tuck your sweater, roll your sleeves to show your watch, and for the love of God, iron it,” I responded. “Also, cuff your jeans once.
Once.
Don’t baggage cuff them. And please clean your mirror before taking ghetto felon murder vibe selfies.” One hour later I received his response. He sent another photo.
Shirt still half tucked. Sleeves still rolled. But rather than your basic_underachieving boyfriend he looked like a vision of menswear purity that could have been posted on an Instagram account captioned “Everyday Sunglasses Guys Should Own.” He killed it with Sarah’s parents.
She still loves him. And he still texts me before any outfit occassion of importance. Moral of the story?
The difference between a basic and a great outfit is often not the clothes you wear, but how you wear them. Ever wondered why every seemingly basic Instagram outfit looks so damn good but is made up of all the same pieces every other guy already owns? I have too.
So I spent way too much time picking apart what makes these setups work and why they look so much better than yours. The result: a compilation of every trick I’ve learned from years of professional Instagram stalking (it’s my job so I have no choice) that stylists use to make even the simplest of outfits look exponentially better in photos AND which of these tricks can actually be applied IRL. Think about your favorite fitted piece of clothing.
How does it fit? Really fit. Most guys’ clothes either don’t quite fit or are too big in all the wrong places.
The second you look at someone’s outfit on Instagram, you know it’s Photoshopped…unless it’s ridiculously well fitted. Not too tight, but not loose. Just on the body the way it was intended to be worn.
The sleeves hit perfectly at the wrist. The shirt is loose enough to be comfortable, but not so loose that it poofs out. Pants break once, no more, no less.
I’m not saying I didn’t wear fitted clothing before I “got into fashion.” But once I started paying attention to how my clothes fit, I realized I had been dressing like a potato sack inhabited by a small skinny person. My shirts would pile up around my armpits and bulge out at the waist. Jeans would balloon at the ankles and legs unbutton.
I looked like a pudgy toddler dressing myself for the first time. When I started buying clothing that fit my actual body shape (not the body shape I imagine I have in my head), everything changed. I even dropped down a jean size at my go-to brand because my pants actually fit me instead of me forcing my legs into toddlers jeans.
Styling Trick #2: One detail should be slightly imperfect Take notice of how most Instagram outfits have one “casual” detail. Half tucked shirt (AKA the “French tuck” Tyler Florence made famous, but allegedly borrowed from fashion icon Tan France), rolled sleeve, unbuttoned top button, you get the idea. This small piece immediately tells the viewer that you tried at some point in getting dressed, but aren’t trying too hard.
It’s intentional unkempt-ness. And it’s why every “style” Instagram you follow has a team of people obsessing over these details off-camera. I would spend forever ironing my dress shirts only to watch my photographer friend David casually push out one of my shirt buttons so it wasn’t perfectly aligned with the others. “It looks too stiff,” he’d tell me. “No one walks around like that.” He’d break one of my shirt buttons, roll my sleeves unevenly, or strategically pull my shirt out on one side.
Suddenly my pre-photo shoot “trying too hard” sack dog getup looked effortlessly sexy in photos. Maybe it was forcing my shirts to be slightly off-center, but everything looked better with one imperfect detail. Instagram Trick #3: Perfect proportions Proportionally speaking, most Instagram wins are a careful balance of fitted and relaxed pieces.
Skinny jeans + boyfriend sweater Slim-fit t-shirt + straight leg pants Tailored blazer + straight leg trousers When I first started really paying attention to my style, my go-to “look” was basically just “everything fitted.” Slim jeans, slim shirt, slim jacket. I looked like a sentient sausage casing. As soon as I started mixing and matching my slim jeans with slightly more relaxed shirts and slim button ups with boyfriend jeans, BAM.
Holy style upgrade, Batman. Suddenly my outfits looked stylish… and more importantly flattering. Similar concept to above: most fitted basic garments come in atleast two colors.
But the guys that stand out on Instagram seem to master what I call color-blocking without even trying. Instead of exact matches, take notes on how most stylish guys stick to similar colors and color schemes. Maybe a blue shirt, grey pants, and light blue sneakers.
I didn’t realize how effective this form of color matching was until I went through an entire month without doing laundry in my twenties. Not drunk, Kanye-style. I just didn’t bother going to the laundromat one week and lived off the same handful of jeans and shirts.
All of them were some variation of blue and grey. Together, they looked way better than my usual “what color didn’t I wear this week?” approach and started paying attention to the little things. Confidence is key.
Literally. Every single time I’ve been on set to have my photo taken, no matter who’s taking them or what I’m wearing I am told some variation of, “act natural,” “you’re going to look great,” and “don’t worry about the camera.” Because if you frown or look unsure of yourself in an outfit, you ruin the look. Confidence is contagious, and sometimes translates into photos.
Same concept applies to real life. I once watched my roommate Trevor walk into a wedding wearing one of those rental suits that 6 other guys were wearing that day. But he walked in looking like he owned the room and clearly was the most stylish guy there.
I asked him what his secret was and he looked at me funny. “Duh,” he said. “I just like how I look in this suit.” He rocked that crappy rental suite because he actually enjoyed wearing it. His confidence came through in his posture, his demeanor, and how he carried himself. And if there’s one styling trick that will always work… it’s that.
Instagram tricks that do NOT work in real life: Instagram Trick #1: Don’t actually wear your clothes Ah yes, the infamous “drape don’t wear” method. Every flattering Instagram pic has a coat draped over the model’s shoulder as if they were half way into putting it on, but never actually bothering. Sure it looks cool in a static photo.
But throw that model into real life and they’d spend the whole time trying to actually wear their jacket like a normal functioning human being. Lesson learned when I did the “coat drape” once at a fashion week show and it fell off after 3 minutes, spilled someone’s champagne, and got stepped on by like 4 different people. Clothing that’s been pinned or clipped behind your back to make something marginally tight look picture perfect.
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Unless you want someone walking around with you all day secretly adjusting your clothes whenever you pose for photos, you’ll never be able to replicate this trick IRL. Solution: Get your clothes tailored. It’s the single most important thing you can do to ensure your clothes fit you to their maximum potential.
You’ll be amazed at how a few adjustments here and there can make even the most basic jeans look like they fit just how you want them to. If you’ve ever stared at your closet in frustration wondering why you only have “basic” clothes but can’t seem to look as put together as your favorites Instagram dudes… add some accessories. They’re the difference between eating plain pasta and eating pasta with actual sauce.
Yep, I was that asshole into his twenties who didn’t think wearing a watch was necessary if you wore accessories. Then I discovered how much of a difference adding something as simple as a bracelet, cool pair of glasses, fun socks, or a sweet belt can do for an “basic” outfit. It doesn’t have to be miles down the Kanye deep end either.
Sometimes one small accessory can tie your whole outfit together. TRICK: Every outfit tells a story. What story are you telling?
When you look at your favorite Instagram stylists, pause for a second and not think about the clothes they’re wearing. Where do you picture them going? What are they doing?
Who are they with? Every single great outfit you see tells a story about the wearer. Sure, you can throw on clothes and hope it works…but why not make it easy on yourself and tell a story your outfit easily conveys?
Shirt’s not too stiff. Jeans are faded but not destroyed. Boots are messy but intentional.
Jacket has personal meaning but doesn’t scream for attention. Done and done. Think of that third piece as the icing on your outfit cake.
Jeans and shirt? Basic. Add a jacket, overshirt, or cool belt and suddenly it looks like you put some thought into it.
That’s why you see so many dudes layer on style Instagram; it instantly makes even basic tee and jeans combos look put together. Pairing jeans and a t-shirt? Throw on an unstructured linen blazer or a chambray shirt to beef it up.
Dates at home? Try an oxford over a plain t-shirt. Going to the bar?
Wear a casual sweater over a collared shirt. Basic shirt and trousers? Throw on a vest and bam, dad style.
Buy a cool watch you actually like wearing. Get a belt that fits you properly and matches most of your pants. Throw on a hat and learn how to actually wear a hat so you don’t look like John Deer retrieved it from the bottom of his tractor.
Spend more time maintaining your clothes than buying new ones. Get your clothes professionally tailored. Hang dry your delicates.
Learn how to properly iron clothes so they actually look fucking ironed when you’re done. Take care of your grooming, too. Trim your nails.
Keep your hair trimmed. Get a weekly blowout if you need to. Pair those bright blue jeans with a white shirt and off-white jacket and suddenly your outfit has a story.
You look intentional. You tried. And it only took seconds and one additional article of clothing to accomplish.
Styling Trick #7: Add a Third Piece Outfits almost always consist of two pieces: a top, and bottom. Throw on a third piece and instantly you’ve gone from wearing clothes to crafting an outfit. That’s why you see so many guys layer on jackets and blazers on style Instagram.
They know that adding one additional component instantly takes your outfit from boring to bangin’. Got a light wash tee and dark wash jeans? Throw on an untucked shirt and see how it changes the entire vibe.
Date night at home? Wear a button up over your tee. Throwing on a blazer to night drink?
Wear an open knit sweater over your button up. TRICK: If you only take away one thing from this article, let it be this. You can have the coolest clothes in the world, but if your outfit doesn’t fit correctly, it will always look basic.
If your jeans aren’t hemmed to your actual leg length, they’ll always look sloppy. Have a shiny new watch? Make sure your shirt is rolled and tucked correctly so the brand doesn’t peek out.
Not spending enough time on your grooming?
No matter how nice your clothes are, you’ll always look basic AF. You can’t always control your hair, facial hair growth, how your shoes get scuffed over time, but you can make sure the pieces you do buy are put together properly.
Everything else will fall into place. I spent $400 on a blazer I loved the other day, only to realize at photos it looked horrible. Low and behold my shirt wasn’t ironed properly, I didn’t steam my blazer after taking it out of the shipping box it came in, and I hadn’t gotten my hair cut in God knows how long.
Same blazer, better grooming and fit = 10x better photo. Put time and intention into how you dress every day. It’ll show.
You’ll feel more confident. And your mom will be proud of you. Now go apologize to your mom for that giant shirt you wore to her wedding. (Hint hint, Marcus)
