How To Dress Old Money Style

How does a man dress like "old money"? To build an old money wardrobe for men, you'll want to invest in high-quality, classic pieces that can be mixed and matched to create a polished and refined look. Here is a detailed breakout of the clothing items you'll need.

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Timestamps:
0:00 - How To Dress Old Money Style
1:01 - Rule #1: Quality over Quantity
2:15 - Rule #2: Timeless Elegance Over Trends
3:10 - Rule #3: Focus on the Fit
3:30 - Rule #4: Stick with a Conservative Color Palette
3:49 - Rule #5: Maintain Your Clothing & Accessories
4:37 - Rule #6: Accessorize Wisely
5:19 - Rule #7: Confidence is Key
6:45 - Basic Item #1: Suits
10:56 - Basic Item #2: Dress Shirts
13:48 - Basic Item #3: Blazers & Sports Jackets
15:21 - Basic Item #4: Shoes
18:14 - Basic Item #5: Polo Shirts
19:18 - Basic Item #6: Neck Ties
20:43 - Basic Item #7: Khakis
21:28 - Basic Item #8: Accessories

#menstyle #mensfashion #oldmoney #oldmoneystyle #oldmoneyfashion #mensstyle

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[RealMenRealStyle]

Do you dress old money style? Comment below!

[MichealGumbert]

I went to college and then lived in what is considered an "old-money" town and the one thing that I noticed about the place was the comfort that people seemed to have about dressing up. So when I really started to pay attention to that I noticed that families would have their children dressed up for more than just special occasions to they grew up being comfortable in nice classically stylish clothing but additionally they saw not only adults dressed that way but their friends as well. True old-money people are just comfortable being dressed up and while I know to a degree it does show a certain status in life, the one's I've meant are less concerned about showing that status and more concerned about being respectful of the world by looking good while in it.

[kimberlyperrotis]

As a woman, I think this channel has the best advice for dressing men in a way that’s attractive to us women. Don’t try to look trendy, try to look classic, elegant and timeless! Quality fabrics and fit are high priority, too.

[lntgbmw]

My mother is a professional chef who only works with respectable Italian families, her last job, before retiring, was as one of the Italian "mafia" lawyers. After the man of the family passed away, he left a closet of unworn high-quality clothing and shoes they planned to get rid of. Even though I am financially successful, I could not bare the fact of such waste and requested to send me those pieces. I must say it was a wonderful and unique experience. As a man in my late 20s, I never had a chance to see how men of the last century were choosing their style.

[phillyboy]

Yes, at 69, I still do. My pop taught me how to dress, mom taught me why to dress, great combo. Pop was wearing custom silk suits in the 50’s, always had on a tie and a pocket silk. I like to keep 2 custom made suits and 6 upper end men’s stores suits, I also keep 6 custom dress shirts along with 6 store bought. Pop taught me to always wear what makes me comfortable, never worry about being over dressed. Before I retired, I worked for a Company where the corporate meetings were a joke with how people dressed. My first year, I showed up in suits, slacks and Blazers and an after 6 white jacket and black tux pants for the awards dinner. The next year, almost 50% of the men now wore suits with ties and by the 3rd year, it was close to 75%, and many were now the young bucks. I was happy to teach and they were willing to learn.

[jasonmitchell]

I’ve in my 50s now, and have been dressing this way since high school. Nobody is ever going to fault you for wearing a Brooks Brothers button down and khakis to work. V-neck sweaters never go totally out of style. I have knit ties my Dad wore at Yale in the 1950s that came around again when I was in high school in the 80s, and have made appearances again since then. Beyond Brooks Brothers, there are other brands that hold their value, and are expensive but not prohibitively so. I’d rather have three Hermes ties than thirty ties from Dillards. I bought a Joseph Abboud blazer in my 20s that I wore for more than twenty years. Bottom line: quality and good taste at the start save money and embarrassment all the way through.

[ct]

This is exactly how my father taught me to dress. Stick w classics. Neutral colors. Buy high quality and take care of it. You're right, a high quality, well-tailored suit is about as comfortable as anything you've ever put on.

[shermanbyas]

Simplicity, elegance, timeless. Perfect.

[jasonvoorhees]

What you said about Thrift Stores...just GO! The ones in or near higher income neighborhoods generally have better stuff. This winter, I got 3 freaking BEAUTIFUL (and timeless) coats, and enough shoes that if I stop now, I still don't have to buy shoes for a few years. The key is that I stop into the store (for me, Veterans of America) at least once per week. By doing this, I can spot the new donations quickly. I know the menswear section so well that it only takes me about 10 minutes to scan it all, and I buy ONLY high-quality pieces that are in like-new condition. Sure, it's true that sometimes I leave empty handed, but I've found it's worth it.

[gergemall]

I’m in my sixties and have always loved the “old money look “ that I review to as the classic look . Quality materials . Brookes Brothers . Ralph Lauren etc . I find deals and sometimes splurge . I have been very sick for three years and lost too much weight. I finally went out a month ago and visited my favorite men’s stores to purchase a new wonderful wardrobe to feel better with clothes that fit. That’s when I found you Antonio . I thank you so much for helping me as I make my comeback. I’m still in Physical Therapy and going to start swimming and getting my muscle tones back’ ❤ love the shoes too ‘.’

[abhimawa]

The old money rules that I know is to attract the least attention with the least hassle (maintenance, reliability, timeless; that’s why they go with tried&true idea) and maximum comfort. Unless you’re the crème de la crème type, it is advisable to blend in nicely & respectably. As for fit, the best thing we can do is to maintain our ideal physique. Having said that, mindful lifestyle (eating, exercise, hygiene) is necessary. Good video btw, Antonio! 👌

[mannyb]

Dressing old money is essentially dressing the way our fathers used do, time-tested styles, classic, tasteful, pleasant to the eye. They spent in quality without breaking the bank but without going cheap either.

[survivalSC]

There is nothing better then an Italian custom suit or sports coat that is tailored to you. When you wear it you know it’s you at your best. Everyone needs that 1 power suite that says I have entered the room

[sprezzatura]

Another advantage to classic style is that your attire is not a distraction. The focus is on you. People should remember you. Not what you are wearing. Even if they pick up on your style subconsciously. Think of your style as the frame surrounding a great painting. Yes the frame should be suitable and dignified, but the focus is on the painting. I detest the current trend of some people to dress like cartoon characters. Sadly it is a byproduct of the attention economy.

[sams]

I’m 31 & I’ve been dressing this way since my late teens. I always found it sort of grounding. I never had a huge budget but looked for high quality pieces in sales. I rarely buy high street now. I used to get called dull (in terms of style) by some but I guess jokes on them. I still have clothes from my early 20s

[ruwanfernando]

This was such a great video Antonio. I look forward to these so much. Not having any surviving male relatives, you've become something of a sage uncle to me and I value the work you put in to make us all a bit better each day. Just wanted to say a big thank you.

[thehighlander]

These clothes are classics in men's attire -- one will never go wrong with any of these pieces because they have always remained stylish. As Ralph Lauren would say, style over fashion. The key theme is understated elegance and comfort within a strict colour palette. As to shoes, the captoe is the most formal -- you will typically see mostly black captoes in the City of London, one of the old world hubs of finance where these clothes are primarily worn.

[kimberlyperrotis]

Antonio, I’ve noticed over the last decade or so that many European men are adding a soft, loose, silk scarf in subtle, manly colors to their plain, more casual outfits. I like this so much better than wearing nothing around the neck with two very plain, solid-color separates, like a sweater and slacks. For occasions where a tie, my preference, might feel too dressy, I recommend that men try this alternative. It’s so much more interesting than, say, just a plain navy sweater and gray trousers, and the colors in the scarf can help tie the colors of the separates together, too. I also really like a white, or other flattering, light color, shirt collar and cuffs showing from under a sweater, that, too adds interest and polish. A scarf wrapped around the neck can also cover chest hair, which can be a good idea. What’s your opinion on this?

[Sandalwoodrk]

The old money look may not fit me very well, but the points from this video that are truly timeless are
Fit is king and
Take good care of your clothes

Clothes can last a lifetime but only if you treat them like they're gonna be with you for the rest of your life

[HMMarcon]

Great video as usual, Antonio!
In the last few years I moved countries and now I'm starting on a sartorial path. I started with a minimal cheap set to live off (some cheap online Made to measure shirts and trousers). Now I'm upgrading it to high quality items and it makes a huge difference and very happy I did not commit to the fast-fashion at any point (they don't seem to fit me anyway).
I also noticed a sharp improvement in productivity since I started dressing up. Each day I feel more comfortable in what I wear and I feel it expresses who I am.
Keep up the great work, we all love to watch and learn!