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  • Writer's pictureSean

7 Basic Starter Tips for Classic Menswear

Hello all, my name is Sean, and welcome to my blog. This is my first ever blog post, so here's a brief introduction into what I'm about. I love classic menswear and fashion. One of my specific interests is finding deals, and methods for upping my fashion game while still on a tight budget. Hence my moniker "Working Class Dandy". Most people are under the impression that dressing in a classic menswear style is only for well to do or rich people. In fact, a lot of people I meet on the street assume that I am far more well off than I actually am. The truth is, that anybody can dress in this style if they truly want to. Whether you want to dress in this style all the time, every day (like me) or you just need to confidently look good for an upcoming event (such as a wedding, or formal party) I'm here to help! All you need to get started are the general menswear rules, what to look for, and where to look. As for the general rules, that will be the topic of this blog post, so let's get started.


1. Know the difference between a suit and a blazer/sport coat:

A sport coat is the most casual of the 3 types of coat in this style, they usually, but not always have some kind of pattern, non-metallic buttons, and do not come with a matching pair of pants.


A blazer is more formal than a sport coat, but less formal than a suit. It’s similar to a sport coat in that it is a coat by itself without a matching pair of pants, but it is made from a solid colour without any patterns, and metal buttons (silver, gold, or brass).


A suit is the most formal of the three styles and is defined as a jacket and pants made out of the same material, and are made to be worn together, although you can also wear your suit jacket as a separate (but don’t worry about that right now, just focus on the basics). So many people go to a thrift store and find a black jacket, and some random black pants and then say they are wearing a black suit. This is not the case. If a coat and pants are not cut from the same material, it's not a suit. Furthermore, you should not wear a jacket with too close a color to your pants, because then it looks like you are trying to make two separate pieces into a suit, and it ends up making you look a bit sloppy. It's especially obvious when the black coat and black pants are two different shades of black!


2. The button rules:

If you’re wearing a suit style coat, remember if you have it closed with the button, only button the top button, and never the bottom button.



The exception is if it’s a 3 button jacket, then you would button the middle button, and the top button is optional, but still never button the bottom button.

Without the top button buttoned.

With the top button buttoned.


There’s a few different theories as to the origin of this practice, but we don’t need to concern ourselves with that right now, for now just know that these jackets are tailored and cut with that fashion rule in mind, and so if you do button the bottom buttons, they don’t look right, and they don’t drape on the body right. So even though it might seem nonsensical to have a button you aren't supposed to use, they are tailored that way.


3. Sitting and standing guideline: Unless you’re going for an intentionally more casual vibe, the general rule with this style of coat is: if you’re sitting, unbutton your coat, when you stand, button it back up.


4. Guidelines for fitting: When I was young, and didn't know about fashion, I thought if a piece of clothing could go on my body, then that's all I needed for it to "fit". It wasn't until I started learning more about fashion, and tailoring that I realized so many of the articles of clothing were far too large for my body. Fit is of the utmost importance, you can have a $5000 suit, but if it's ill-fitting, it will look bad, no exceptions. Fit is the difference between looking like you know what you're doing, and looking like you're wearing your grandpas clothes as a costume.


Button up shirt sleeves, as long as you are wearing long sleeves, should end at your wrist, and never go past. I've seen so many men wearing dress shirts that are way too big, and the sleeves go down all the way to their thumbs, and it looks terrible!

Correct sleeve length.

Incorrect sleeve length.


You can wear a blazer/sport coat/suit jacket with a short sleeved button up shirt sometimes (or even a more casual shirt than that) depending on the circumstances, the weather, the function you're attending etc. Most of the time, however, you will be wearing these styles of jackets with long sleeve button up shirts, and in that case, you want your shirt sleeve to be showing a little bit under your suit jacket. Usually about an inch to an inch and a half of sleeve is ideal. If your jacket is the same length as your shirt sleeve, to where no sleeve is showing, this can also be okay, but your jacket sleeve should also never go past your wrist, the same as shirt sleeves, if your jacket is going down to your thumb, it's way too long! Don't make this common mistake.

Showing some shirt cuff
Jacket's sleeve is same length as shirt sleeve.

Example of jacket that is too large. Sleeve is way too long.


How long your pants should be is to some degree a personal preference, but there are definitely some concrete rules. One of those is, do NOT let your pants drag on the ground. If your pants are dragging on the ground, they are either too long for your legs, or they are not pulled up high enough. Some dress pants are still made in the tradtional high waisted style, meant to go near or around your navel, but a lot of men no longer wear their pants on their navel, so they put them on the way they put on their regular jeans, and so they end up dragging the ground. Don't be a victim of the dreaded pants puddle. Some people prefer to have their pant legs end just barely touching the top of the shoe or right above the top of the shoe. Some people prefer for the pants to go as high up as above the ankle. Both can look good if you know what you're doing and the rest of your outfit is in a similar style. The above the ankle pants is more of a modern fit, whereas the barely above the shoe pant leg is a more old-school fit. If you're wearing modern fitting pants with an older style fitting jacket, or vice versa, it can sometimes look like a bad match. So, until you feel more confident in putting together an outfit, try to keep more modern fitting pants and jackets together, and also the more classic fitting pants and jackets together.

An example of somewhere in between classic and modern pants length.

A more modern style pants length. Ends well above the ankle.

More classic style pants legth. Resting on the top of the shoe.

Same pants as above, but if not pulled up to around the navel/natural waist.As you can see, they become too long, and begin to "puddle" around my feet.


5. To wear a tie, or not to wear a tie: In most settings these days, ties are not required (dressing up is usually not required in most instances either to be honest) so unless you're in a setting where a tie should be worn, the choice to wear a tie or not with this style of clothing is up to you and how much clothing you feel like putting on from one day to another. A suit (or similar style jacket) can look just as good without a tie as it does with a tie as long as you're wearing your outfit with confidence, and the rest of your outfit fits well.


Examples of the no tie/open collar look.

The most common practice if you're going tieless, is to keep your collar button unbuttoned, so you have an open collar. If you're just starting out, this would be what I would recommend if you're not wearing a tie.


Example of the no tie/closed collar look.

You can also look good buttoning up your collar without a tie, but it's a more rare look.


Example of undershirt poking through the open collar. Looks a little sloppy.

If you are going without a tie, try to make sure that your undershirt (if you are wearing one) is a lower cut, or a v-neck. Generally speaking, you don't want the top of your undershirt to be visible from the open collar of your button up shirt.


6. Tie guidelines: If you decide you do want to wear a tie, the length is a big stumbling block I see in a lot of people. The tip of your tie should be ending up around the waistband of your pants. If a tie is too short it can look cheesy, and if it's too long, it looks sloppy. Unless you're going for a "Sprezzatura" style look  (i'll discuss sprezzatura in a future post.) you should tuck the tail of the tie into the little band on the back of your tie. All ties should have this, unless it's been torn off in the case of buying a used tie from a thrift shop.

Correct tie length, with tie clip.

Correct tie length, with no tie clip.

A tie clip is optional, but can add that extra little bit of flare to an outfit to help you stand out from other people, and is also useful for keeping your tie from flopping around, which is doubly helpful if you're in a situation where you might be leaning over food and other such things (you don't want your tie dipping into the mashed potatoes). A tie clip is also helpful in the aforementioned case of not having a loop on the backside of your tie to put the tie's tail into.

If you decide to wear a tie clip, it should in most cases, go between the 3rd and 4th button of your shirt, counting the collar button. I wear mine normally right under my 3rd button

The color and style of tie clip is, most of the time, unimportant, but use your best judgement for the scenario you are walking into.

Various styles of tie clips.

I have a lot of fun and unique tie clips, but for instance, if I'm going in for a job interview, I would choose a simple bar style clip that's either a solid silver or gold color.

_________________________________________________________________________ 7. The pocket square: The pocket square is definitely my favorite of all the common menswear accesories. It's also the one that you can have the most fun with. It is not a necessity for classic menswear but it adds so much pop and color to a suit jacket/blazer/sport coat that now I personally don't ever leave the house in one of those styles without a pocket square.

Example of the same suit, with and without a pocket square.


When choosing a pocket square, it is generally advised to not have one that is an exact match to your tie (if you're wearing a tie). It can be confusing for beginners, because many stores sell sets that come with a matching pocket square and tie. There's nothing wrong with buying these sets if you like the patterns, for the record. My advice would simply be to wear the tie and the pocket square on separate occasions. Unless you have no other options. It looks much better to have a pocket square that can compliment your tie, and the rest of your outfit, but also has a bit of contrast to your outfit.

A warm, tweed sport coat looks great with autumnal colored pocket squares.


Similarly a light weight summer style sport coat looks great with floral or more brightly colored pocket squares.

In truth, there's very little limitations. Almost any pocket square can look good with almost any suit jacket/sport coat.


How you put in your pocket square is also up to you, or dependant on the situation you are in.

The easiest and most obvious way, is to just pile it in, and let a bit peak out in a kind of a poof ball shape.


You can also do simple, or very elaborate folds in order to add even more flare to your outfit.


Or if you are in a super formal situation, just a basic square fold, and letting a little bit of the edge peak out over your breast pocket is the usual way to go.


That's it! With these basic and simple guidelines as your foundation, you should be ready to jump into the world of classic menswear with confidence.

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