Good Looking Loser’s Guide 

-What Not to Wear & Common Style Mistakes-

By: Good Looking Loser & Taylor (w/ Friends)

With respect to DJ Pauly D and friends, these clothes were once somewhat stylish but they aren’t anymore. So don’t be caught dead in them.

Caution tape image courtesy of “Yellow and Black Warning Tape” by FrameAngelwww.freedigitalphotos.com

 … don’t be caught alive in these clothes either.

Forward by Good Looking Loser

Let’s face it- straight guys, even sexually active straight guys, have problems picking out or just spotting clothing that works.

Our fashion IQ’s are low.

To be honest- mine isn’t that super high either, but it’s higher than most guys.

I get compliments on my clothing/style all of the time and I have whole panel of pretty girls [working for me] that talk about fashion as much as we talk about girls.

This is telling because in my early 20′s- I wore a fair amount of clothes from high school including hockey jerseys, Reebok Pumps and Abercrombie & Fitch. I felt out of place when I was at anything other than a college party.

Sometimes- you can read a style guide such as “Good Looking Well-Dressed Loser Wardrobe (L’essential)”with high-quality images and pick out a few items or styles that will work for you.

Sometimes- it’s better to see what DOESN’T WORK and learn why it DOESN’T WORK.

Knowing what NOT TO WEAR and WHY is often half the battle.

Be warned though- you might have ditch some of your clothes, or return them if you bought them at Nordstorm or Kohl’s.

Either way, you’ll be better off and you can be certain that you are doing the right thing and don’t look like a reject from hell.

Girls don’t brag to their friends that they met a “reject from hell.”

Common Mistakes that Guys Make

From what we’ve noticed, 98% of the “mistakes” that guys make on their style and clothing will fall into one (or more) of six categories.

Rather than reflecting “hot,” “cool,” “exciting,” “fun,” “sexy,” and “high-status,” these sub-categories tend to reflect specific undesirable characteristics and allow females make specific negative assumptions.

We discussed these negative characteristics and assumptions at-length over sugar-free hot chocolate, strawberries and heavy whipped cream.

The negative characteristics and assumptions are usually subconscious, but are powerful nonetheless. They ALL lower your perceived social status.

These are just some short comments on these mistakes, this is by no means a comprehensive profile, it can run much deeper.

Keep these elements in mind when evaluating your style, what’s in your closet and whether you should make a purchase.

Over-styled (Mr. Try Hard)

This is prominent in bigger cities because of the desire to stand out. The mindset to “stand out” is good, but the specific clothing selections might not be..

If you are going to break a fashion law- it’s better to get busted for being over-styled once in a while, rather always being under-styled and blending in with the wallpaper and all the other guys that don’t date hot girls.

In general- your clothing looks like it has too much “going on”. Usually it reflects multiple images and that you have a low fashion and social IQ.

The result is a guy that “stands out” for the wrong reasons. Girls assume he is an attention whore but actually he is very insecure. If he is good looking – he will look “try hard”. If he isn’t – he’ll look extra “dorky” and be accused of dressing up as something he’s not.

I don’t want this one to scare you though, all the others are worse and I still encourage you to experiment with your style and look. I’ve been guilty of this one. You should too, at least once before you die. 

OVER-STYLED- This is a case where long hair hurts the look and ages him. The bandana around the neck needs to go. And the belt buckle should be in the center. Also the bracelets are out of date and the belt shouldn’t be brown.

OVER-STYLED- OUT OF DATE-

No Ed Hardy! Especially on your shirt, ankle sweats and hat. This is wayyy too much of a bad thing. It looks so try-hard! And the cheap flip-flops don’t help the look either.

Under-styled (Mr. Insignificant)

This is the opposite of “over-styled,” as you might assume. It is actually the most common mistake according to us.

Think plain. Plain styles. Plain colors. Boring. Average wallpaper.

Many guys are afraid to stand out and think fashion is for girls and gays so their default solution is to dress poorly in order to be themselves.

“Mr. Insignificant” is exactly what it reflects. A basic, boring, under-sexed guy who lives a boring life, works a boring job, tells uninteresting stories and is probably average in bed.

Unless they are good looking, the first impression they make on hot girls is- none.

UNDER-STYLED- It’s important to see that under-styled doesn’t necessarily mean under-dressed. This guy is trying not to be boring, dressed in layers (more on that later) but the look sucks.

Immature (Mr. Abercrombie High School Lifeguard)

This will make guys look too young. If you are young, you will look way too young.

It suggests “boy” instead of man. Inexperienced, probably will run in a fight, probably sucks in bed, penis might not have finished puberty.

I don’t have to explain why that is bad.

IMMATURE- Don’t wear Hollister looking shirts unless you are in high school or a frat. Columbia is a cheap brand too. These guys are good looking, but they’d be more masculine in “big boy” clothing.

Out of Date/Not Current

(Mr. Out of His Sexual Prime)

This guy wears clothing that is out of style OR clothing that is old and never was cool.

The assumption made is that the guy can’t relate to the “in crowd” and he’s an outdated outsider that no one a cool girl would want to be seen with. He and his friends probably can’t relate to cool people.

It’s assumed that more than just his clothes are “behind the times,” he is old news too.

OUT OF DATE, TOO OLD- If this guy were in his 70′s he would be dressed pretty well. But he’s not, so this outfit ages him. The cardigan sweater paired with diarrhea colored corduroy pants don’t give off a sexy vibe. The brown belt is also bad.

Obvious Generics

(Shitty Inexpensive Knock-Offs) Mr. Poser

This is my favorite. I invented the category name and I’ve actually been guilty of it on a few occasions – but never after 2009.

Mr. Poser is a guy who is trying to wear sexy, cool, current clothing but is wearing an obvious cheap replica. You don’t even have to be a fashionita to tell.

In my case, it was a few “fake me out” Affliction shirts that I got from Target back in 2006. It had a few of the typical [formerly cool] Affliction elements- skulls, shields, distressed sleeves- but it was clearly a crappy cheap t-shirt. Even my Mom knew.

There are a lot of assumptions made here- he is poor, he is not too popular, he is a follower but too stupid to do it correctly (haha).

This can be avoided by just wearing the brand names. Remember- you only need a couple of outfits that you like and are cool and current. No need to spend money you don’t have.

Ironically, Mr. Poser is a follower, but a guy who wears brand names isn’t. As long as he doesn’t look like a billboard. But that’s just how it works.

OBVIOUS GENERIC-

This is an obvious Ralph Lauren Polo or Tommy Hilfiger rip off. It looks cheap and the pants look cheap too.

Clothing that Doesn’t Fit (Mr. Idiot)

This is most comment among guys with the LOWEST fashion IQ’s and is sometimes even done intentionally- small shirt on guy with huge muscles or extra long shirt on a guy that telling the world that he’s a thug.

Regardless if it is intentional or unintentional- it always looks awful.

It tends to make the guy look either too young or too old because young teenagers and seniors tend to be the ones that sport clothing that doesn’t fit because they don’t have a current fashion IQ.

More importantly- women make the assumption that the guy doesn’t care how he looks and lives a lifestyle where he doesn’t give a shit or have a strong passion for anything. Even if he’s not, girls assume he is probably deficient in a lot of ways. Regardless if he has a good body or not, it will make his body look worse. As superficial as it may seem- girls, especially attractive girls, would not want to this “slob” around her friends because it will reflect very poorly upon her.

Here are three examples of this-

DOESN’T FIT RIGHT- Deep V-neck Tee (already a bad choice). When the neck hole is super deep it either looks gay (which there is nothing wrong with, but you don’t want to put off a gay vibe if you’re straight) or Jersey Shore “fist pumping”. This shirt is too tight. It accentuates his out-of-shape chest and you can see nipples (Big No, No). It shows his fat-tire/love handles around his waist. There are pull lines around his stomach, which makes the fat on his stomach stand out. And it’s too tight on his arms. Very unflattering.

DOESN’T FIT RIGHT- These jeans are too baggy and long, which is why they look scrunched up. Go with more fitted jeans. The shirt looks too baggy around the waist too.

DOESN’T FIT RIGHT- Obviously way too baggy. This style was popular for a while as we all know and it didn’t look good then either. Don’t buy clothes that say Sean Jean on the front of them either.

DOESN’T FIT RIGHT- This shirt is obviously too tight. When shirts are this tight they don’t show off your physique, they make you look try hard. And pink is okay on guys but not in tight, deep V-necks with white accents. This looks feminine.

Bad Looking Shirts:

• BAD BASIC T-SHIRTS:

UNDER-STYLED – OBVIOUS GENERIC- Basic Hanes T-shirt. Don’t wear shirts that look like cheap clothes from Walmart. This shirt looks like it is a cheap Hanes T-shirt. The fabric is too thick, too crisp and the sleeves are too loose and slightly too long. Also maroon isn’t a current color, which doesn’t help.

OVER-STYLED – DOESN’T FIT RIGHT- Basic black deep crew-neck Tee. This guy is trying too hard to be sexy. Leave the deep crew-necks for the women, they look too try-hard on guys. The shirt is also too tight, especially the sleeves.

OVER-STYLED- He is trying to have a cool “I don’t care” grungy style but he’s trying too hard. The shirt is too tattered because of all of the holes. And the neck is bordering on too deep V territory, which isn’t good. It needs too look a little cleaner with less holes.

• BAD GRAPHIC TEES:

OVER-STYLED – OUT OF DATE – IMMATURE-  These guys are trying too hard to be edgy. The big cursive writing is too try-hard and cheap looking. The sculls and the big 8 with the diamond graphics are out of date, immature and try-hard. And side note- The long hair and mustache need to be chopped off!

OUT OF DATE – IMMATURE – OVER-STYLED- No Ed Hardy! It’s out. It looks like you are trying way too hard and you’re not current.

OBVIOUS GENERIC – OVER-STYLED – OUT OF DATE- This is an obvious Affliction rip-off shirt. Affliction was very trendy a few years ago, but now it’s out. So don’t wear it. It looks like your trying hard to be cool and you’re not current, which translates to girls as being a loser (and not a Good Looking Loser), just a loser.

OBVIOUS GENERIC – UNDER-STYLED- You can tell this shirt is from Walmart. It is an obvious generic college shirt. It makes you look like you aren’t cool and you might be cheap.

IMMATURE- Abercrombie & Fitch is for high school age. Once you graduate high school you should ditch the Abercrombie & Fitch!

• BAD BUTTON-DOWN SHIRTS:

  

  OUT OF DATE- This is pretty self-explanatory. Not only is the print out of date it’s hideous, the colors are bad and there are flowers on it. Please don’t be caught dead in a shirt like this.

  

  OVER-STYLED- I can’t even say this shirt is out of date because I don’t think it was ever ‘in date’. Camo is hard to pull-off and this is definitely an example of how NOT to wear it. Someone thought this would be cool and it’s not. The camo is so misplaced and it looks like you’re trying too hard when you clearly have no sense of style. Take out the camo and this shirt would be fine with some accessories.

  

  UNDER-STYLED- This shirt wouldn’t be bad if it was accompanied with some accessories like a nice watch and a necklace or stud earrings. The jeans are good. But this is an example of how button-downs can make you look like too much of a “nice guy” and make you blend into the crowd. This guy’s haircut isn’t helping the look either. He needs to shorten it and get it cut into an actual style.

• Bad Plaid Shirts:  

OBVIOUS GENERIC – UNDER-STYLED- This shirt looks cheap. It shouldn’t be buttoned up so high because it makes him look even more dorky. The jeans also look cheap, which makes the whole outfit look cheap. You could maybe pull this shirt off as looking good if you undid the top button, put on some nice, dark, fitted jeans, earrings and  did your hair in a current style.

OVER-STYLED- This shirt would be fine without the white top-stitching. When it comes to plaid keep it fairly simple. The plaid pattern has enough going on that adding much more on the shirt cheapens it. It also makes you look like you’re trying a little too hard to be cool.

OVER-STYLED – OBVIOUS GENERIC- Another example of how adding too much to plaid cheapens it. Plaid should not have graphics. It looks cheap and try-hard. And this is another shitty Affliction knock-off graphic.

OUT OF DATE- This shirt is an ugly shade of brown first and foremost. This style of 1970′s cowboy plaid is out of date. It is cowboy or rodeo plaid because of the pointed shoulder panels, the style of pocket and the solid accents.

Bad Looking Pants:

• BAD JEANS

  

  IMMATURE – DOESN’T FIT RIGHT-Skinny jeans are hard for guys to pull off. And they are a little immature looking. Only thin guys can pull off skinny jeans bigger guys shouldn’t even try. And even on these skinny guys it makes their legs look tiny in proportion to their body. You want more of a balanced legs to upper body proportion. Also the 80′s stone wash on the right is immature and looks try-hard.

  

  OUT OF DATE - Stay away from Wrangler jeans. They are out of date and make you look dorky and aged. This is also a bad cut. They are too narrow at the ankle, which accentuates this guy’s bigger thighs.  They are also too long which is making them scrunched up from the knee down.

  

  OUT OF DATE – OVER-STYLED- True Religion jeans with the big stitching is out as of 2012. And they look try-hard. These jeans also have too much fading.

  

  OVER-STYLED – IMMATURE – OBVIOUS GENERICS- Jeans don’t need graphics. And none of your clothes need dragons. The big dragon trend has long been over. These are immature and look like you have to overcompensate with a big dragon patch for being ugly.

• Bad Khaki Pants

   

  

  TOO OLD- Dockers type pants age you. They channel a dad or a grandpa and girls don’t want to fuck their dad or grandpa.

OUT OF DATE – IMMATURE- These khakis are out of date, not flattering and boring. The pockets on the side are out of date and make the pants look to young. The crotch is a little too long and the fit is slightly too baggy.

OUT OF DATE – IMMATURE-These cargo khakis are out of style. They are too wrinkled. They have too many pockets. and the drawstrings at the bottom are not good. They also make you look too young.

• BAD DRESS PANTS (SLACKS) 

  

  OUT OF DATE – TOO OLD-These slacks are out of date because they are a little too ballooned at the top. They will also age you because they are old man slacks. And when it comes to black and brown clothing- go with black it’s sexier.

OUT OF DATE- These dress pants would not be bad if they were not corduroy and they were not brown. The fit and cut are quite good. Corduroy is out of style so keep it out of your closet.

IMMATURE – OUT OF DATE- OBVIOUS GENERICS- Dress pants should not be too loose or baggy. They should also not look cheap and crappy. They should be fitted. Baggy pants are out of style and they make you look immature. The waistbands are too wide. And these colors are not the best either.

• BAD SHORTS

  

  OUT-OF-DATE- If you have any fashion IQ you know not to wear jean shorts. These are out of style and make him look dorky.

  

  OUT OF STYLE – IMMATURE-The over-worked, worn-out cargo shorts are out. They used to be very popular but not anymore. These shorts are way too long. Shorts should touch your knees but not go below. The pockets are too big and bulging. And There is too much top-stitching. If you do cargo shorts keep it more simple (less going on) and balanced (no ‘big’ areas). Avoid dark brown and wide-leg.

   

Bad Looking Shoes

• BAD SNEAKERS

  

  IMMATURE- Athletic shoes that you would wear to the gym shouldn’t be worn with jeans. These shoes are too athletic. And as a rule of thumb- avoid Velcro on your shoes as well.

  

  IMMATURE – OVER-STYLED- High-tops are not sexy.  They are too hi-hop looking for the most part. They make you look too young as well. They are also too sporty to wear with jeans, even though that look is a trend from time to time. It is a trend you don’t need to follow.

  

  OBVIOUS GENERICS- Spend a little more money to get brand name sneakers. Go with brands like Nike or Under Armour. Just get one good pair. These shoes are obvious cheaper versions of New Balance and it’s noticeable.

   

• BAD DRESS SHOES

  

  OVER-STYLED – TOO OLD- These shoes don’t need to be woven. This detail ages you. The brown is bad and they are too pointed.

  

  TOO OLD- These shoes are literally too old. You shouldn’t wear old, worn-out shoes. It makes you look cheap and ages you. The brown and suede are not fashionable either.

• Bad Boots

  

  OUT OF DATE- No Timberland boots. They are out. And they make you look like a construction worker who doesn’t have a lot going for him. Not sexy.

  

  OVER STYLED- No cowboy boots. Riding boots are okay but cowboy boots are too much, unless you live in Texas. They make you look like you’re a try-hard dork.

  

  OUT OF DATE – IMMATURE – OVER- STYLED- 

   

  No combat boots. They are Gothic looking. They are over-worked (too much going on). But mainly they are Gothic looking, which is a depressed teenager look.   

  Bad Looking Jackets

  

  OUT OF DATE – DOESN’T FIT RIGHT – TOO OLD- This blazer is too boxy. Blazers should be more fitted (slightly tapered in at the waist). Don’t wear corduroy or velvet jackets. And this tan color isn’t our first choice for blazers. Black is our first choice. 

  

  OUT OF DATE- Leather jackets are actually very in style right now. But you want a current cut and color. This jacket is too boxy and brown . And the collar is too small and a bland color. Go with black leather that is a current cut and more fitted. 

  

  IMMATURE – OUT OF DATE- This isn’t a bad jacket for younger high school aged kids. It used to be very in style. But it’s too young to be wearing after the age of 19 and it’s out of date now. It’s too wrinkled and there are too many pockets, like the long cargo shorts we showed above.

  

  OVER-STYLED – OUT OF DATE- Fur on a puffy jacket is way too much. Even when puffy jackets are in, I wouldn’t recommend them unless maybe you’re going skiing. They add too much volume and they aren’t fashionable.

  

  UNDER-STYLED – IMMATURE- Again, unless you’re going skiing you don’t need to wear this type of outdoor sports jacket. It looks dorky and communicates that you don’t have good fashion sense. It isn’t sexy.

  Bad Looking Underwear

• BAD UNDERWEAR

  

  OUT OF DATE- Boxers are out of style. They aren’t sexy. They get bunched up under clothing. So make the switch to boxer briefs. Calvin Klein makes some high quality, fashionable boxer briefs.

  

  OUT OF DATE – TOO OLD- Tighty-whities  are out. They are not sexy, they remind girls of their grandpas, especially when the waistband is so wide like these ones. Burn your tighty-whities immediately.

• Bad Socks

  

  IMMATURE – OUT OF DATE- Socks aren’t that big of a deal. They rarely show. But you don’t need to wear socks with sculls or flames on them. These trends are for punk rock kids and will make you look immature and not fashionable. Just keep it simple with socks- black and white work for most occasions.

  

  TOO OLD- Spend a few dollars extra to get socks that will last a while. Don’t wear socks with holes in them. Throw away your holey socks, now. They make you look dirty and cheap. And they may be hidden under your shoes, but you never know when your shoes could come off if you invite a girl back to your place. You don’t want her getting grossed out and turned off because of you holey, nasty socks.