Confusing Men’s Style Rules

“I don’t understand fashion; it’s weird”

“I’m not wearing those old styles”

Many guys make statements like that about menswear.

I admit that there are some old style customs that seem outdated.

But so many guys are still following them

This article will discuss 7 weird style traditions or rules and the history behind them.

#1 Why Do Surgeon Cuffs Have One Button Unbuttoned?


If you have surgeon cuffs it’s incredibly difficult to get the sleeves adjusted. In fact, it’s advised not to tailor surgeon cuffs. The majority of off the rack suits are not designed this way.

For this reason, the surgeon cuff signals that the suit is bespoke. The one button undone is a subtle way of showing you have a custom-made suit.

If you want to take it back further, this style element gets its name from days when there were more physicians on the now iconic Savile Row than tailors.

Once the suit makers moved in, they catered to their clientele by designing jacket their clientele by making jackets with functional sleeve buttons that could be unfastened and rolled back like shirt sleeves.

This feature gave the Doctor the ability to work on a patient without removing his jacket, which is in stark contrast to the purely decorative and non-functional buttons that are attached to most suit jacket or blazer sleeves.

#2 Why Is the Bottom Buttonhole On Dress Shirts Horizontal?


Have you noticed that the bottom buttonhole on your dress shirts are different than the rest of the buttonholes? It’s actually a practical design feature.

The hole is sewn horizontally so that the buttons can endure more stress from pulling/movement than the others without stretching out the shirt or the hole itself.

Think about it – the bottom buttonhole is usually going to be tucked in around your waist or over your butt. That’s area is the epicenter of movement for you and the shirt will be pulled and moved all over the place.

If the hole was vertical like the ones on the chest and torso, the stress from the movement would pop it off. Being horizontally placed gives the button more wiggle room. There’s also more stitching around the lowest buttonhole. It provides stronger reinforcement so that the button stays in place.

The buttonholes on the torso are vertical so the shirt can have the best fit possible. Additionally, the top button in the collar is horizontal for the same reason.

#3 Why Do We Wear Antiquated Accessories?


As we’ve discussed over and over again, accessories are necessary enhancements to the overall look of an outfit.

They can take an ensemble from “eh” to wow. So from a style perspective – they’re necessary to be the sharpest version of yourself. One such example is the pocket square.

Without it your suit or jacket looks plain and boring. The pocket square adds a pop of color to the largest item of your outfit. It helps to break up the monotony of one continuous fabric.

Accessories should also be worn for pragmatic purposes. Items such as watches, Cufflinks and tie clips/pins have uses that go beyond style

Watches must be worn. They tell time and help keep you punctual. Timepieces have evolved with technology (smart watches) and can be an advantage throughout your day.
Cufflinks hold the sleeves of your shirt together and act as a weight to keep the sleeves down.
Tie clips or pins hold your necktie in place. This is excellent for when you’re eating or moving around continuously. They help keep your look crisp.

The added bonus is that each of these items help add to the overall aesthetic. They come in a bevy of different designs and can be customized so that your personality can truly be expresse

#4 Why Do We Use Monograms?


This style of monogramming dress shirts is a tradition was historically practiced as a way to identify a man’s shirt when it was sent to be laundered. Nowadays it comes down to a personal choice. The trick to monograms is to be discreet. Using discretion, you have 3 decisions to make.

Placement – the monogram should not be visible when wearing your jacket. Your initials should be on the sleeve placket or on your chest. When getting a monogram on your jacket, it’s customary to place it under the collar or on the inside flap of the jacket.
Font and Size – the font should be reflective of you and the size of the letters should be small enough that they wouldn’t be easily notice when wearing your shirt with no jacket or sweater.
Color – remember discretion is the name of the game so the color of the thread that you use for the monogram should be the same color (and thread) as your shirt. It’s okay to go a shade darker but not anything that’s a huge contrast.
Monogramming is about personality more than anything, so let you’re shine brightly. Just do so tastefully. You don’t want the letters to be so bold that they take away from your outfit.

#5 Why Do We Match Metals & Leathers But Not Ties & Pocket Squares?


Are there any rules for matching? Yes!

What are they?

The rules for matching solid fabrics is clear so I won’t dive too deep into that. What a lot of gentlemen get confused on is how to match certain details…or even when to match them.


It’s best to match the metals in your outfit as much as possible. You want to avoid the appearance of over accessorizing or having your accessories being unbalanced. If you have gold cufflinks with a stainless steel watch and a gunmetal bracelet, it’s going to look messy and not uniform. Choose one metal and wear on all pieces of jewelry.

Note: if you have a two-toned watch, then pick the more dominant metal and match your other accessories to it. Also, you don’t have to match your wedding ring with the other metals. Some guys do, but it’s not a mandatory thing


All of your leathers should match – or at be as close to matching as possible. The outfit just looks better when the leather from the belt, shoes, and watch strap matches. It creates on smooth palette. When all of them are the same it catches the eye and helps to bring out the details in the shoes or the face of the watch.

Pocket Square and Tie Combo

It’s been tradition not to match these two accessories. When you match them with identical fabrics and patterns, the look can become very busy or noisy. Follow these side guidelines:

Tie and pocket square can have different patterns but the main colors should the same
Solid tie with patterned pocket square; the color of the tie should be expressed the most in the hanky
Patterned tie with solid kerchief (should be the same as the main or boldest color in the tie)
White straight-fold pocket square looks great with any tie and jacket

#6 Why Do Suit Parts Differ From Each Other?


Suit jackets have many different style elements that are important. Most notable are the lapels, pockets, and vents.

There are 3 types of lapels: peak, notch, and shawl. In my estimation, there are two main considerations when knowing which lapel to sport: occasion and body type.

Where you’re going generally dictates what kind of jacket you’re going to wear – and different jackets come with different lapels. As a generalization:

Peak lapels are almost always on double breasted jackets
Notch lapels are on single breasted and modern/slim fit jackets
Shawl collars are the most formal thus found on tuxedos
Now exceptions do exist. For example, it’s not at all uncommon to find peak lapels on single-breasted jackets. The above list are the traditional conventions.

As it relates to body type, peak lapels draw the eyes outward giving you a wider look. You want to take that into consideration if you’re a larger guy.

#7 Why Do You Leave The Bottom Button Undone?


Never button the bottom button of your jacket. 

It’s an old tradition that dates back a few centuries. One school of thought is that since vests and jackets were worn at the same time, you wanted the jacket to peak open a bit so that the best could be seen.

Another perspective is that the bottoms buttoned being unfastened allows for better movement and comfort for the wearer. In fact, modern suits are now constructed with the assumption that the bottom button will not be fastened. As a result, buttoning it will not allow the jacket to fit properly.

This convention applies to double and single breasted jackets.

Vests have jolted into the young man’s wardrobe in recent years but there are rules when wearing waistcoats. One of which is that the bottom button should be open just like a suit jacket.