top of page
  • Writer's pictureStefan S.

The Old Money Aficionado

Updated: Jul 27, 2023


You are an Old Money Aficionado.

For you, nothing beats sitting on the Italian Riviera at a coastline café with a cup of coffee in the morning, in your white linen shirt and tan pants.

You have an exhaustive collection of loafers: from brown leather to navy suede, from penny- to bit- and from shiny to matte, as well as all the shirts in the world you might actually want.

Though you are not tied to wearing a suit, you still embrace traditional fashion and despise the dreaded fast fashion. Thus you are free like a bird.

Let's be honest, you are probably a younger man that has impeccable taste and knows how to appreciate good quality. You are not satisfied with dressing like the average 99% of men - you know you deserve something more. So, while your friends are saving up money to buy that new pair of Yeezys, you are instead adding a nice Tissot watch to your collection.

During mornings you are either at a café by the seaside, having a croissant on your way to work or walking briskly through the town. At lunchtime, you know this very chic little restaurant that simply makes the best pasta in town. At night, you can be found in the town center, on a terrace, enjoying a fresh Mojito or a Hugo.

"The joy of dressing is an art." —John Galliano


5 Rules Every Old Money Aficionado Should Know

1. Socks Or No Socks? The Tricky Question

The story goes like this:

  • If you are wearing loafers: You can wear socks if you want. It's optional. Loafers can be worn both ways. HOWEVER, never wear loafers sockless with a suit. I would personally advise against wearing loafers with suits altogether.

  • If you are wearing dress shoes: Never, Ever, Ever wear them sockless. Ever.

2. Never Mix Leather Colors

This is the no.1 mistake you could make that would get you from "Successful Fashion Icon" to "Boy in a Adult Clothing" in less time that it'd take for you to say "Poor Taste". If you wear black shoes, wear a black belt and a black watch strap. Same goes for brown, blue or whatever other color you could think about wearing.

You know what? I'd even go as far as saying that it's better to not wear a belt and a watch at all than to commit this atrocity.

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. 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. Tuck In Your Shirt

I see a lot of men make this mistake. There are two types of shirts:

  • Those that have a flat bottom line: Under no circumstances should they ever be untucked

  • Those with curvy bottom lines: They can technically be worn untucked. However, I would not recommend it. It looks childish.

For a more mature look, don't forget to tuck that shirt in.


5 Items Every Old Money Aficionado Should Own

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

1. 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".

2. A Dress Watch

It is a common misconception that diver watches shouldn't be paired up with suits. This is wrong. But even though they can be worn underneath a suit jacket, dress watches are still preferable.

3. A White Linen Shirt

It's the Old Money signature shirt that every man should own. Wear it on a yacht and you will feel truly invincible.

4. Brown Leather Loafers

Classy, elegant and lightweight, the loafers will make you stand out from the sea of sneaker lovers out there. The great part is that there are so many different types of loafers to choose from. It's an entire ocean.

5. A Knitted Sweater

If you truly want to look Old Money, grab a knitted sweater and throw it around your shoulder. Best colors to choose from are navy, cream, tan, green and burgundy


5 Great Outfits Every Old Money Aficionado Should Try Out - Inspiration

Want to read more?

Subscribe to to keep reading this exclusive post.


Recent Posts

See All


Rated 0 out of 5 stars.
Couldn’t Load Comments
It looks like there was a technical problem. Try reconnecting or refreshing the page.
bottom of page