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  • Writer's pictureStefan S.

The Classic Gentleman

Updated: Jul 27, 2023


You are a Classic Gentleman.

You have a burning passion for men's fashion and everything it entails: from ties to pocket squares, from cufflinks to tie clips and from signet rings to dress shoes - you want to know all there is to know about everything.

At this point, fashion is no longer just something you wear, it's something you experience, something you live. You want to know all there is to know about different suit fabrics such as wool or tweed and are interested in vintage items such as old pocket watches and signet rings.

Fashion makes you feel superior. It make you feel like a lone wolf, looking at civilization from the edge of a cliff, ready to unleash your next move.

One of your favorite past time activities... well, other than shopping for new accessories and suits, is watching all kinds of movies. But you are not simply watching them. No, you are analyzing the outfits people are wearing and getting inspiration for your next shopping spree.

During mornings you are either having a coffee at your favorite country club, reading a book in the park or driving your convertible to your workplace. At lunchtime, you prefer to have a home cooked three course meal and at night you dine in style before watching "Roman Holiday" or "The Godfather".

"Elegance is not standing out, but being remembered." —Giorgio Armani


5 Rules Every Classic Gentleman Should Know

1. Never match tie and pocket squares completely.

Both the tie and the pocket square have three main characteristics (tie also has length and girth but that's besides the point): color, pattern and material. These three attributes will be present in every single tie or pocket square you will ever own.

And since I just know there will be a know-it-all out there that will comment this, let me get it out of the way from the start: Yes, black and white are not technically colors and some ties/pocket squares will lack a pattern, but even the lack of either color or pattern is still an attribute worth mentioning.

So what do I mean never match them completely? While purists will tell you that none of the characteristics should match, I personally believe it's alright for one or in some cases even two attributes to match, but never all three. This is basically because you never want to make it look as though the tie and pocket square are part of a set. That will make them look cheap and it will make you look like you don't know what you're doing.

2. Always Pay Attention To The Suit Jacket Button Etiquette

The rules are simple:

  • If you're wearing a two button jacket, never unbutton the lower button

  • If you're wearing a three button jacket, fastening the first button is optional, and fasting the lower one is, yet again, not allowed

  • If you're wearing a double breasted jacket, always fasten all buttons, except for the lowest outer one, which is optional.

Furthermore, you should also know that:

  • When sitting down, ALWAYS unbutton every single button, UNLESS you're wearing a double breasted suit, in which case you don't have to unbutton anything.

3. Always Align Your Front

Three things must always be aligned in order for your outfit to look presentable. You placket, your belt frame and your pants' fly piece. If any of the three is misaligned, your whole outfit will look out of place.

4. To Wear Or Not To Wear A Belt: That Is The Question

Well, though that might be the question, the answer is quite simple. I see a lot of people promoting belt-less suit pants nowadays and I simply can't wrap my head around it. A good, sleek belt that goes well with your leather shoes will always bring your outfit to the next level, so why would you forgo it?

There is, however, one suit that should never, EVER, be accompanied by a belt, and that is the three piece suit. It's a rule that shan't be broken. Opt instead for a nice pair of qualitative suspenders.

5. Never Over-accessorize!

Look, I know it's tempting. I know you take pleasure in wearing accessories, because, after all, they are just as important as the outfit itself.

An outfit is made of three components:

  • The Clothes

  • The Accessories

  • The Shoes

But where some men go wrong is when they take that extra step and go from suave and subtle James Bond to shiny bling-bling SoundCloud rapper. You've heard that it's better to overdress than to underdress, but now let me do you one better:

It's better to under-accessorize than to over-accessorize


5 Items Every Classic Gentleman Should Own

These are the 5 items we at the Gentlemen's Order recommend every Classic Gentleman to possess in order to elevate their outfits and style:

1. A Tweed Suit

Polyester and Woolen suits are everywhere, but do you know what classical, dapper suit is very rarely seen nowadays? Tweed suits. Wear one and you will either feel like Prof. Keating in Dead Poets Society or like a member of the Peaky F***ing Blinders (Pardon My French)

2. A Pocket Watch

Just think about it. You turn up at your city's classiest event of the year in a tailored three piece suit. Someone asks you the time. Do you look at your wrist like an average Bob, or do you take this bad boy out of your vest pocket? That's what I thought.

3. A Boutonnière

Next time you have a formal event like a wedding for example, make them an offer they can't refuse with a dashing boutonniere. I'd personally recommend a red rose.

4. A Signet Ring

This is the easiest way to go from "Guy in a suit" to "Italian Mafioso" faster than you can say "Family Crest".

5. A Fedora

This one is definitely not easy to pull off, thus I recommend it only to the most advanced fashion experts. There is a fine line between dapper gentleman of the last century and shy quiet kid in the back of the class. And believe me it's one you do not want to cross.


5 Great Outfits Every Classic Gentleman Should Try Out - Inspiration

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