Anyone can look good. Consult the right blogs. Ask the right sales associate. Drop the right amount of cash and anyone can be king shit for a day. Even the most basic bro looks good at least two times in his miserable Dave-Matthews-loving life. Almost every man who has ever lived has looked or will look relatively dope at their wedding and their funeral. So fret not, if you think you're going to bat .000 your entire life.

And then there are those style Jedis among us who know how to look good for any occasion. These are the men that execute a perfectly sensible and attention-grabbing outfit for meeting the in-laws, poker night, Thanksgiving dinner, and everything in between. You will likely never get to that level, but even these bespoke lords know their limits. There are some times in life when you will not look good and there is nothing you can do about it.

That's right fashionable men and women of America: there are some occasions where you will not be able to stunt. In times like these, no blog can assist you, no accessory can save you, no pocket square can bring that outfit together. The good news is that every one of us has the power to become a man who knows when he has no hope of looking good. Let's talk about those times in life when you will not look good, and how to deal with it.

Image via Awkward Family Photos

Family Portraits

Sometimes a Nobel laureate is born to the illiterate. Sometimes a star athlete is born to the uncoordinated. And sometimes a future baller is born to the basic. Alas, not all of those destined for fashion greatness are raised in families who know how to dress for success. If you are asked to lower yourself a few levels to match the rest of your kin for a group photo, fear not. No one looks good in family portraits.

How to Deal With It: If you find yourself involved in a portrait fiasco, just accept it. Your parents not only pay for the pictures, but they pay for the roof over your head and the food in your stomach. Any attempt at rebellion will just look more embarrassing in retrospect. Swallow your pride and put on the matching suspenders. And remember this moment when you get the urge to force your own child into family portraits several years down the line. Together we can bring an end to this national nightmare.

Image via Tumblr

High School Musical

Damn. They don't make it easy on young artists, do they? While the athletic dudes are decked out in gear that inherently looks cool, plus they get to wear a piece of plastic that makes their dick look bigger, creative kids have to wear tights, make-up, and wigs. The best case scenario is that you are cast as an old Jewish man or a prissy French revolutionary. Otherwise, your choices are generally limited to animals or foppish dandies. 

How to Deal With It: Just be glad you're not in marching band. If you are in marching band, just be glad high school only lasts four years. Once you get into college, you get to bang artistic girls with tattoos and mild drug addictions while the guys who made fun of you stay in your hometown, start having kids, and begin unstable, unfulfilling lives. So, I guess I'm here to tell you it gets better. Kind of.

Image via Pinterest

Senior Prom

Any aspiring swag lord in training encounters his first great challenge in his senior year of high school. Yes, you've probably looked terrible for several dances and a few homecomings before, but here the stakes are higher, and the odds are high that you'll look your worst. And it won't even be your fault. In prior years, your date was content to let you wear a Men's Wearhouse tux seven sizes too big or even your dad's navy blazer and your older brother's khakis. Senior year, young ladies tend to pull out all the stops and their dates pay the price. The clueless man, who is so desperate to whisk his date back to the Motel 6 or some random bedroom at the afterparty, bows to their dates' every whim. This can lead to wearing a florescent orange vest or sporting a sparkly bow tie because it "goes with" the dress that old girl found on discount at the Fashion Bug.

How to Deal With It: Young man, you have to make a careful calculation. You want to get laid on prom night. The question is, how badly? If you really want to hit it, obey her wishes, no matter how stupid they make you look. If you see your chances at scoring fading away, push back against any ridiculous requests your date makes in the name of coordination. You might still be able to score a make-out session with someone else if you ditch the neon pink paisley vest.


Halloween is a beautiful night where the women of the world put on costumes designed to make themselves look as attractive as possible and men do their best to look like assholes. I hear your protests already, "But, I spent a month trying to find the perfect color dress shirt to pull off Gus from Breaking Bad." "Yeah, but, people tell me I look like a young Pacino." "No, don't you get it? I dressed as the Communist Party, and my stupid fucking party hat has a hammer and sickle on it." Trust me and everyone else; you look like an asshole. No matter what you're wearing. No matter what current pop culture moment you're referencing. No matter how savagely your offensive costume sticks it to the status quo. You. Look. Dumb.

How to Deal With It: Just don't be the guy who explains his costume to a girl in hopes of wooing her. Before you go out, look in the mirror. Pretend someone just asked you, "So what are you supposed to be?" If your answer is longer than one sentence, change.


Your First Internship

Before I begin, let me say to any interns assisting with this piece, you look good baby, I'm not talking about you. So please don't skip over any of my "your/you're" fuck-ups in an act of retaliatory grammar checking.

Interns always look stupid. The unofficial uniform of the intern is a baggy-ass dress shirt their mom got them from Kohl's because lord knows they can't afford to buy their own clothes, a tie with diagonal stripes so broad they could double as construction warnings, and pleated khakis that their older brother used to wear before he got a real job.

And that, sadly, is the ideal situation. The worst is when interns try to "make an impression." This means they either show up to a casual office in their grandfather's three-piece suit, or they take "casual" to mean they can finally put their high school wardrobe from Journeys and American Eagle to good use once again. 

How to Deal With It: Accept that office dress codes are hard to decipher. The correct business attire may take you months to decode. Make adjustments as you see fit, and be prepared to fail. In a few years in the working world, I've noticed the following professional wardrobe guidelines, and I'm sure there are thousands more. Entrepreneurs wear jeans and a blazer. Executives wear suits. Writers wear button-up shirts with the sleeves rolled up. Artists wear whatever the fuck they want, unless they want to wear a tie, because artists never wear ties. Film crew wear shirts from previous films they've worked on. Techies wear wrinkled, dirty anime t-shirts.  Advertisers and marketers wear button-up shirts with the sleeves rolled down and no tie. High-end salesmen wear a button-up shirt with a tie. Low-end salesmen wear the company t-shirt or apron. And fashion people the most absurd shit imaginable.

It's daunting, but in due time you'll crack the code and find yourself in a position to mock interns who don't have a clue about dressing appropriately in the workplace.

Being a Groomsman

The purpose of groomsmen and bridesmaids, in addition to attending to any bitch work that needs done and sleeping with each other after the reception, is to make the bride and groom look good. These days, the entire purpose of a wedding is so Aunt Mabel can say that ya boy Steve looks "so handsome" when he stands in front of that altar, and for the guests to pop off a few 'Grams. You're going to be dressed in oversized pants and an ugly cummerbund to help make sure that's how it goes down. You probably won't have to endure the kind of unspeakable fashion cruelty that a bride can perpetrate on a bridesmaid, but you are going to look pretty stupid. And you are going to have to take a bunch of pictures wherein you do all manner of cutesy bullshit at the behest of the females present. It comes with the territory. Just be thankful that you aren't a bridesmaid. 

How to Deal With It: Keep your head down, smile, and remember that the reception is only hours away. Yes, you look like an idiot, but once all of the ladies have 15 gin and tonics in their system, your rented tux and peach vest are going to start looking pretty sexy. If you don't get laid, may I recommend killing a thirty pack of Budweiser in the Holiday Inn pool after the reception? The happy couple probably won't be too pissed off if they end up paying for any damages you incur. They already doubled their debt so they could throw a party in a converted barn with mason jars, linen table clothes, and strings of white Christmas lights. What's another few hundred bucks on the old credit card?

The Gym

Here's the only style rule you need for the gym: the harder you try to look good, the worse you look. Think back to the most heinous gym outfits you've seen. That guy in the spandex body suit; that guy with the self-cut tank top that barely covers his nipples; the guy wearing street clothes in the weight room, etc.

All of these guys looked in the mirror and thought, "Damn I look good. Today is the day the girl on the treadmill notices me." Here's the sad truth brother: She is never going to notice you. She is going to stand there on the elliptical reading Eat, Pray, Love, flipping through Redbook, or watching the local news wishing she knew how to change the channel and do her best to ignore the world around her. And you, you're the world around her. The last thing a woman wants to do is talk to you, and spending $300 on Under Armor so you look like a spandex-clad clown is not going to change that.

How to Deal With It: Dress cheaply and comfortably, and focus on your form instead of peacocking around the gym in your Tough Mudder T-shirt. The gym is where you get results, not where you show them off.

When You're A Dad

Let me be clear: It is possible to dress well after you have children. But it's impossible to dress well when you are fulfilling dad duties. What, exactly, are these fatherly responsibilities? These include, but are not limited to, meeting your daughter's prom date, coaching your kid's soccer team, taking them to the mall, and going on shitty family vacations. However, the primary duty of a father is to embarrass their children. This, apparently, trumps any working knowledge of fashion they may have gathered up to that point in life.

How to Deal With It: Thankfully, I don't yet know what it's like to be a father, and I certainly don't understand the secrets of dadcore style. I would suggest finding the worst dressed dad on your block, the guy with like seven Margaritaville hats or the guy who wears velour jump suits to run errands or the guy who wears thick wools socks with sandals. Find this man and seek his counsel. Only then will the secrets of fatherhood fashion be rightfully passed down to the next generation. Please, young fathers, keep the flame of embarrassment alive. You're our only hope.

There you have it. This may not help you dress any better, but at least you'll be prepared when you dress your worst.

Brenden Gallagher is writer in Los Angeles whose Halloween costumes are just as shitty as yours. Send photographic evidence of your personal fashion low points his way at @muddycreekU.