How to Dress Classically Masculine

5 style lessons from icons of classic masculinity like James Bond, Cary Grant, and Don Draper.

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Timestamps
0:00 Intro
0:48 Rule 1
1:48 Rule 2
3:09 Rule 3
4:52 Rule 4
5:45 Rule 5
7:33 Conclusion

[b.johnathanwarriorinagarde]

Let's bring back fountain pens as well.

[iammaximus]

“A well dressed person,
Is a sign of Good Manners.”

#tomford

[bdcochran]

1. I am older and retired. As a young man, I went to Brooks Brothers. It has a custom tailoring unit. See a style on the rack. Get fitted in all dimensions, choose the material, options like functional buttons on cuff or whether you want a vest. Went and bought multiple and identical paris of British businessman's shoes. The quality of what I bought is that I still have some and they appear brand new.

Eventually, I followed one of the tailors who left Brooks Brothers and who opened up a shop in San Marino, CA.
I bought Dress for Success and bought the first of a number of tuxedos and wear them.

I partially raised a brother in law. He started at the bottom in the construction industry. Doesn't have a college degree. When he got to the point in construction that he had a trailer, I had him put a Brooks Brothers suit and dress shoes in the trailer so that he could go to meetings. It is years later. Tomorrow he is taking the train to Washington DC and doing business.

[Mr._Martinez]

Your videos are so nicely articulated my friend.

[MrFenris]

My favorite accessory is a watch. I collect watches, and I love the idea of matching my wristwatch with my outfit. Whether it's a day by the pool or a night out with my wife, I love the idea of having the right watch for the occasion.

[djohnson-kucl]

An older gentleman told me all of this can be summed up by one thing, the goal of a gentleman is to make a woman look good. You don't want to upstage her but make her the star. She's the center of attention.

[trinity]

Couldn’t agree more about watches, they show a hint of class that a smart watch is incapable of producing. They also fit the simplicity model you described to a T..

[erikhn]

If you are on a budget, don’t feel ashamed to buy second hand. Apart from sustainability, you can actually buy classy quality clothes - even brand new. So many people go on holiday and get carried away in fashion shops in e.g Milano, Paris, NY or London, spending all to much money. And when they get home, they compensate by selling it to a fraction of the original price. Don’t just by anything because it’s a good offer. Like buying new stuff, you must know, what you are after and must be selective with your purchases. But then you can get far using this road in combination with buying new stuff when needed.

[jibeneyto]

Cufflinks are terribly underrated. Using shirts without link cuffs is a missed opportunity.

[MM-vvmt]

I inherited my father's late 1960s Omega Seamaster Cosmic wristwatch with a fine steel shark mesh Milano bracelet and paid $300 to have Omega in NYC clean it and replace the scratched crystal. Like many former military men and engineers of his generation, he always wore his watch with the face on the inside of his wrist; I do likewise in homage to him. Evidently, there is a practical reason for this: it prevents the crystal from reflecting the sunlight which could attract unwanted enemy attention on the battlefield, and it also protects the crystal from getting damaged. I think it also shows off the bracelet to great effect. I've had women remark about how I wear my watch differently than most men. Details are everything in fine style!

[weiyuan]

2 videos less than 24 hours apart? We’re getting treated like kings haha

[peterblum]

Quality boots are definitely my tip. They immediately elevate any outfit. They are far better for your feet than cheap boots. And they will last for decades with occasional resoles; in the end, a good $400 pair of boots ends up being much cheaper than a $150 pair that you will throw out in a year or two. My wife said to me decades ago: “I judge people by their shoes. It saves time.”

[nilesroberts]

First, I'm 65, divorced with 20 & 13 year-old daughters, 5'5" with trim build, working full-time as a physician with retirement not in the cards, and live in a small city on the West Coast. My favorite accessory is my late father's 31mm Movado watch which he purchased ~1938 (though a 34mm Longines Master Collection watch with the lunar phase in on my wish list). I also have an A2 ("bomber") jacket. I usually wear a hat, either an Irish flat cap, or a brown Stetson cowboy hat (the "Bozeman"). Leather shoes or boots nearly always.

[alecvesely]

My favorite accessory is a Timex Marlin, new model, with gold accents and a honey colored strap. I have many more expensive watches than this, but this dressy, affordable timepiece from a legacy American company keeps finding its way back to my wrist.

[douglasdietz]

Great channel 👍 Finally classy advice from a classy young man. Keep up the good work.

[ifish]

I watch a lot of YouTube. This is one of the best videos I’ve seen in a long time. Great presentation. Thanks.

[d-resmin]

My favorite accessories are anything I can wear on my lapel. I used to wear printed tees to express what's important to me. When I started dressing nicely, I found that lapel pins were a more mature expression of these things. On top of that, people ask about them and it can get some conversations going. My collection includes a French flag (sister in France, a cross (religious symbol), dove with the word scholarship (area of ministry I serve in), autism ribbon (I'm on the spectrum, a submarine (my dad served on a submarine in the navy), a Texas flag cut into the shape of the state (where I live), a pink cherry blossom (my favorite boutonniere, and the fleur-de-lis (sister in France and friends in New Orleans).

[NigelDeForrest-Pearce-cvek]

Excellent and Outstanding Advice!!! Thank You!!!

[billziegmond]

The Seiko classic looking watch is my main accessory. On special occasions I will wear a diamond ring that was my fathers. More to remember him and his style than to show off. It's a simple ring nothing flashy that says look at me. I always have a pocket square when I wear a suit. Thanks Grams for teaching me her majesty's etiquette.

[Philobiblion]

Excellent vid. I recently traded in my cheap Casios for a Citizen diver that is powered by ambient light of any source (unlike Seiko). It is practical, keeps almost as good time as the Casios, is discreet, but makes a quiet statement, and only cost $300. Plus, nobody in a hurry is going to cut my hand off to get this watch. In the year I've had it, only one person has commented, an attractive and nicely put together lady in my age group (I'm 75 ). She said 'that is a handsome and sporty wristwatch'.