***Reposted from Cliff’s List as my second submission to their website.***

I have to apologize in advance. I’m going to start this style journey like I imagine an abusive parent would; by telling you what you’re doing wrong. 

Last week, I wrote a bit of an introduction of myself and the reasons behind improving your style. It was lovely and lighthearted and I’m sure you enjoyed it. If you haven’t read it, click here to read it and catch up with us. If you didn’t like it, click here to read it again, because you probably read it incorrectly the first time.

Like I said, I’m going to have to apologize, because this week is devoted to pointing out exactly what you’ve been doing wrong. This isn’t to make you feel badly or to permanently scar you in any way, it’s to make sure you understand the mistakes you’ve made so that you don’t make them ever again. Before we stock up your closet with the most beautiful of golden garments, we gotta separate the wheat from the chaff and clean that sucker out! I will try to sugarcoat it as much as possible so you don’t end up leaving hurt and afraid, but I am going to be honest with you: There are problems with your wardrobe.

For those of you that have this under control, we’ll be getting more and more specific as the weeks go on, so don’t give up just yet. For the rest of you; there are two major things wrong with your wardrobe and they can be sorted into two categories, the first of which we’ll address this week:

#1: Fit. You probably don’t know how clothes fit.

Forgive me for being blunt, but like 99.9999999999% of guys don’t wear clothes that fit. Whether you are trying to hide the recently-developed ponch by wearing a shirt that’s two sizes larger than it should, you’re stuck in clothes that your nearly blind mother buys you, or you’re going through a Thrift Store phase that provides you with the ideal garments in the wrong sizes, you aren’t functioning at 100%.

This one’s really easy for me to write about, because I was very firmly planted in that last category for a very long time. I’d go to the Salvation Army and find amazing Versace shirts and Gucci blazers for $6 each and wear them with pride. They were an amazing steal, but they simply didn’t fit well. I wouldn’t end up looking like Robert Plant or Freddie Mercury (70’s Freddie Mercury, thank you), I’d just look like someone improperly squeezed into outrageous clothing. It was not long after I realized I really enjoyed clothing that I began to understand that ill-fitting clothing changes your appearance. I always thought I’d look like me with different clothes on when, in fact, it made me look like I had a completely different body shape. 

Here are the facts, starting from the bottom up.

Step 1: Put your pants on.

A.Your trousers should stop 1/4 from the ground with your shoes on. If they drag on the ground, they will tear and look miserable. Also, if your pants bunch up at the ground, they’ll make you look stumpier.
B. The inseam of your trousers is the length of  your pants from the hem (bottom) to just below your crotch. Your pants should not be baggy. Again, it makes you look shorter and stumpier than you are.
C. The waist of your pants should not bunch when you tighten your belt. 
D. Your pants should not hurt when you put them on. In a perfect world, you wouldn’t have to suck your gut in to close the clasp, either.

If any of these are in conflict, you should take them to a tailor (especially in the case of A, C, and D), trash them, or donate them to the local goodwill. 

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E. When tucked in, your shirt should stay in your pants (NOT YOUR UNDERWEAR) when sitting and standing up repeatedly, if it comes out entirely, it is too short.
F. If untucked, your shirt should only reach to the first joint of your thumb (the joint closest two your wrist – is that a knuckle??) and should not extend below your crotch.
G. Your shirt cuffs should stick out between 1/4 inch and 1/2 inch from the cuff of your blazer. They should be loose around your wrist, but not so loose that they approach your thumb’s first joint.
H. Your neck should button up with room for one finger between the collar and your skin. Too loose can make you look like a bobblyhead, too tight will cause death.
I. The seam where the sleeve meets the body of the shirt should be right on the top of your shoulder. Any longer and it will make your shoulders look droopy, and any shorter and it will make the shirt bunch up weird. The same goes for t-shirts. This is the most important piece of advice I can give you regarding shirts and is the number one problem I see men suffering from. 
J. Extra fabric can look horrible. They make skinny men look frumpy and bigger men look even bigger! Interestingly enough, skinny men AND bigger men can be made to look much more svelte and athletic when their shirts fit properly, as it isn’t the mass of the body, but the proportions, that create a good looking outline. The same goes for t-shirts. When the proportions are wrong, it makes you look bigger/smaller than you are.

Again, a tailor will be your best friend in the cases of F (who will move the button) and J (who will take the sides in). These are cheap and easy fixes. The rest are signs that your shirt doesn’t fit properly and should be tossed or donated.

K. Regarding blazers and suitjackets, the rules of the shoulders and body of the jacket (whether the button is too tight or there is too much space between you and the jacket) apply, but the sleeves should be shorter, revealing the appropriate amount of sleeve.
L. A blazer’s length is easily defined by the tail reaching your first KNUCKLE of your thumb (so, the second joint, the one closest to the tip of your thumb). Again, a long jacket will make you look short, and a short jacket will make you look like… fat guyyy in a litttleee coattt.

These are the biggest problems I see on most men walking around in all different parts of the world. They’re guidelines that will help the lost and confused, so if you know a lot about style, please spare my your specific objections. If you’re really serious about changing your situation, go straight up to your closet and find out what fits and what doesn’t.

Here’s the cold, hard, truth: Don’t save clothes because you think you’ll fit into them after you lose some weight or because the might come back into style one day. This is silly. You’re already reading an article about improving your style, so donate the old stuff to good will and get excited about buying new clothes (ESPECIALLY if you’re losing weight). If you have sentimental t-shirts or sweatshirts that are in bad shape or that don’t fit anymore, think about stretching their logo across a board and framing them like this. It’s a great way to accept you won’t be wearing them again, free up closet space, and still keep them for their sentimental value.

I assure you that the fit of your clothes is the most important element of your personal style. Trends have come and gone because a person can cut a nice figure in almost ANYTHING as long as it fits. Unfortunately, years of growing out of our clothes has caused us to take fit as a general concept, rather than a precise measurement and, the truth is, now that you’re an adult, you won’t be doing a lot more growth, so we can now refine how you look down to the tiniest detail.

If you took this seriously, your closet should be thinning out and next week we’ll go through the last of it by finding out what is classic and stylish and what is trendy and terrible. Then, we can start gathering the essentials necessary to build a great, stylish, and versatile wardrobe.

As always, feel free to email me at Gareth@ArtOfThePlayboy.com with questions you need addressed, follow me on Twitter and Facebook for updates and tips from Art Of The Playboy and my Instagram for inspiration, and check out my past articles at ArtOfThePlayboy.com.

Hope this helps,

-GRMJ