Last Tuesday, I was waiting in line at Jackson’s school pickup. I was scrolling Instagram when Mike from the parent teacher association walked past in what was undoubtedly a $200 golf shirt. You know the kind I’m talking about; supreme padre-collar featuring some tiny polo player making eyes at a croquet bird or whatever.
Only Mike’s shirt looked like it was thrifted from his older brother’s closet. Sleeves dragging onto his hands. Shoulders slouching.
Shirt drowning on his frame. I suddenly remembered a conversation I’d had with Lauren’s cousin Dave a few summers ago at a family barbecue.
Dave works at one of those finance companies downtown.
He makes good money but constantly bemoans how he “doesn’t look professional enough” despite obviously spending a small fortune on clothes. I watched him run his fingers through that khaki blazer that must’ve cost more than my car as I thought… Dude, the problem isn’t your budget. You just have no idea how to wear clothes that fit your actual body.
Which made me wonder: Is this a Thing That Dallas suburban dads do? Or are guys everywhere tricking themselves into wearing bad clothes? To find out, I proceeded to harass random professional stylists on LinkedIn.
Yep, that’s how little I value my sanity. But if anyone knows how to make men look good, it’s people who literally dress CEOs and celebrities every day. They must see all the fashion crimes being committed by husbands and fathers out there.
So I asked them. The response I got was staggering. Menswear stylists inundated me with emails and messages blasting my guy brothers for our collective inability to wear a properly fitting pair of trousers.
One female stylist who works primarily with NBA players responded to my message less than an hour later with “OH MY GOD YES” as the subject line. Another stylist who works with tech industry CEOs forwarded me a manifesto on proper trouser length. These were people who had strong opinions about men’s style, and they were eager to share.
I talked to eight stylists over the course of a couple weeks between conference calls and Sophie’s gymnastics practices. Some common themes started to emerge. But what surprised me most wasn’t what they hated… It was what they didn’t hate.
You would think the stylist community would lose their minds over dudes wearing polyester leisure suits from Target. But almost every single one of them told me that spending money on clothes wasn’t the problem. In fact, they barely mentioned price at all.
Instead, they brought up the same stuff every guy should know about wearing clothes that fit well. First and foremost, fit. Not “make sure your clothes fit”, but how every single one of them could not understand what properly fitting clothes actually looked like on a guy.
Megan, a stylist who worked with a bunch of actors I’ve seen but obviously can’t name due to NDAs, said “Men wear their clothes too big. I don’t care if it’s a $5K suit or something from Target, jeans should fit your actual body. If it’s baggy, you look sloppy.” She told me the story of this high-paying executive who would buy $200 designer dress shirts several sizes too big because he “felt more comfortable.” Then complained to her that he always looked wrinkled in photos.
Dude. Cheap shirt or not, you can’t wear that big and look good. The fabric doesn’t magically tighten around your body just because you spent more money.
Believe it or not, I used to be that guy. Back when I first became a dad I was still a few trousers sizes bigger than I am now and feeling super self-conscious about it. So I’d wear everything oversized thinking it would help disguise my “dad bod.” Spoiler alert: it didn’t.
Only made me look bigger and sloppy. It took me years to learn that clothes should fit your actual body shape rather than the shape you wish you were in or were in 10 years ago. Marcus, who styles everything from finance bros to tech entrepreneurs agreed 100%. “My clients come to me broke down because they’re wearing expensive clothes that look cheap on them because NOTHING FITS!
They think because it’s branded that it looks stylish. It’s actually the opposite.” James, who styles celebrities in the entertainment industry, noted an interesting generational trend as well. “Skinny jeans happened and destroyed men’s concept of what ‘fits’ are supposed to look like. I still see guys today trying to wear trousers so slim that they cannot even sit down!” The truth is that properly fitted clothes fit your body snugly without constricting movement or making you look skinny.
If you have to breathe differently when putting your jacket on, that’s too tight. The second biggest mistake? Proportion.
This was a harder concept for me to grasp at first, but basically, it means making sure all aspects of your outfit are complementary and not fighting against each other. Alicia told me about one of her clients who was only 5’8” but loved to wear these giganticXX-wide ties with large knots because he thought it made him look “powerful.” Instead, it just makes him look silly and childish. Shirt and tie print size matter.
Tie width matters. Glasses frames, wristwatch thickness, even the scale of patterns on your dress shirts are important. Carlos, who styles many athletes, had one client who was a professional football player but loved wearing slim fit dress shirts with tiny patterns that looked “suburban dad” on him.
You Might Also Like
They weren’t too small (they fit his arm measurements perfectly), but the patterns were too small for his larger frame. Made me think about my own wardrobe. I’m not a large guy by any stretch but have always leaned on the smaller side.
For years I wore these bulky, chunky sport watches that definitely didn’t suit my wrist. Lauren would never say anything to me, but damn if looking back through old photos of me wearing those doesn’t make me cringe. Colour was the third thing that came up over and over again.
Apparently most guys choose clothes based on what colours we “like” versus what actually looks good on our skin tone. Diane, a stylist who primarily styles TV and film, relayed a horror story of a client with fair skin and red hair who would always wear bright mint green dress shirts because he liked the way they looked “fresh.” Problem was, they made him appear sickly when filming. Guilty.
When Sophie was about 2 years old so back in 2018, I developed this delusion that I looked good in mustard yellow. I bought a mustard yellow jumper thinking I looked “sophisticated.” Nope. I looked jaundiced.
Lauren wouldn’t outright say anything, but I suddenly stopped seeing that jumper in the laundry hamper. The trick Diane recommended was hold your clothes up to your face under natural lighting. Do your eyes pop?
Does your skin look dull in comparison? If yes, that’s not a colour you should wear. She also said to listen when people say “wow I love that colour on you!” Because that’s helpful info that tells you what colours are actually enhancing your complexion.
Number four was details. Honestly, up until talking to these stylists I didn’t even think about something like shirt cuff finishes or trouser hem styles. Alicia recounted stories of clients who’d spend thousands of dollars on suits but ruin the entire look by wearing shoes with scratches on the toe box or shirt cuffs that frayed beyond the placket. “It’s like building a gorgeous mansion then painting the front door brown.” This definitely hits home for dads because kids love destroying our clothes.
Sophie likes to use my shirts as napkins when she’s eating. Jackson has a special pair of kicking sandals he only wears when he’s near me. But paying attention to wear your shoes look, keeping your shirt collars trimmed, and replacing that falling apart belt isn’t something you should sacrifice at the altar of young children.
Carlos also mentioned dressing appropriately for the occasion. Wearing flash pocket squares with your favourite club sport jacket to pickup your kids from school. Or wearing a smart watch with your favourite pair of jeans to the park.
Don’t get me wrong, I love showing off a nice watch or pocket square. But there’s a time and place for stuff like that. Carlos even had a story about this one athlete client who loved wearing slim dress shirts with big shirts prints even though he had a large body-type.
It looked like he was being choked by his own shirt. Lastly, and several stylists brought this one up, was authenticity. Guys trying to dress in a style that wasn’t authentic to their personality.
Megan told me about this one tech CEO client that would only wear full suit-and-tie because he “should look professional.” Dude looked like he hated his clothes. As soon as they started wearing more casual but equally stylish clothes, he looked a hundred times better. I see it all the time in IT.
Guys who feel the need to dress like Wall Street guys to be respected in the workplace, even though that means wearing clothes that make them feel overly stiff and constrained. On the opposite end of the spectrum, I’ve coached clients who refused to dress past a hoodie and jeans because “corporate clothing wouldn’t fit their personal brand.” Neither of those dudes “look like themselves” because their clothes aren’t reflecting their personality or lifestyle. When I asked the team my big question about what the ONE thing all guys should do to improve how they dress, not a single one of them mentioned buying more clothes.
Marcus told me to invest in a good tailor, not designer brands. Megan stressed knowing your measurements and sticking to those sizes rather than what you wish they were. Alicia told me to pay attention to how clothing makes YOU feel.
If you love how that shirt looks but hates how it feels, you won’t wear it. James suggested really learning how to master the basics before you start buying trendy items that may or may not work for you. As dads, we don’t need trendy pieces we only wear once.
We need stuff we can wear to drop-off, video meetings, AND chasing our kids around at the playground.
Carlos said to dress for your life, not the life you think you should be living. Man, that last one stung.
I used to constantly daydream about having the coolest closet filled to the brim with stylish clothes, but then I’d remember I’m chasing around kids covered in Goldfish crumbs and hand paint 90% of the time. Why worry about getting ruined clothes if I can have clothes that actually fit my life? Practical doesn’t have to be boring, and you don’t need “ Pinterest worthy” outfit photos to look and feel good as a dad.
Trust me, none of these stylists would argue with me about the last point. You can throw as much money at your wardrobe as you want, but if you don’t know how to dress well… You’ll look like Mike from the PTA. It’s more important to invest in tailoring, editing your colours, and mastering the basics than buying clothes that don’t fit right.
And the best part is you don’t need to buy anything new to improve. Get your clothes altered to fit you better, figure out which colours are flattering, pay attention to the damn details. Sometimes the best upgrade you can make to your style is learning how to properly wear the clothes you already own.
