derek guy Profile picture
Sep 16, 2025 19 tweets 14 min read Read on X
Style lessons from Robert Redford, one of the most stylish men in the last century. 🧵 Image
A tailored jacket continues to be one of the most flattering things you can wear. However, for it to look good, it has to fit right. That means a jacket that bisects you halfway from your collar to the floor when you're in heeled shoes. Also trouser + suit jacket silhouette flows Image
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It also helps to know how to use this visual language, especially with regard to ideas about formality. For instance, a dark business suit cries out for a tie. If you don't want to wear a tie, try a more casual garment, like a sport coat. Image
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Or work within the langauge of ties. A matte silk rep stripe of foulard tie is great with a suit. For something more casual, consider a knit tie. Black is a surprisingly useful color for knit ties. Image
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In the 1978 film The Candiate, where Redford plays a politician, you can see the full spectrum of tailoring language. Dark worsted suits, esp in pinstripes, call for neckwear. More casual jackets, such as tweed sport coats, can be worn with casual turtlenecks and chambray shirts. Image
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You can also dress your jacket down with jeans. But it helps to make sure you're wearing a sport coat — not a suit jacket. Image
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Turtlenecks are great for the fall. Get a smooth, merino one in a dark color if you plan to wear it under a sport coat. Or go chunky and textured if you want to wear it with casualwear. But the chunkier the knit, the warmer it'll wear, so be aware. Image
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Black tie is aided by some kind of waist-covering, such as a formal waistcoat or cummerbund. This will hide the shirt that might otherwise peek out from beneath a single-breasted coat's buttoning point when it's fastened. It also looks tidier. Image
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For more relaxed eveningwear, try velvet. Image
The 1970s is often written off as the "decade that taste forgot." But Redford shows how to do it well (these are actually 1969, but close enough). Start with big eyewear frames, a leather jacket, bootcut jeans, and roper boots or side-zip boots. Image
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Or you can mix it up with a Western suit and casual shirt. Nina Penlington is a British bespoke tailor who tours the US every few months. She specializes in making Western suits, among more basic business styles. Image
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Speaking of Western style, Redford was a fount for Westernwear inspiration. Consider the Lee 101 over the Levi's Type 3. It has slanted chest pockets that mimic the line of peak lapels. Or consider a puffer jacket from Rocky Mountain Featherbed. Image
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You can also go full gusto. Or get something as basic as a pair of black jeans, a pair of boots, and raw denim Western shirt (although this one is technically just a basic work shirt). Image
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If you live in an area that gets real seasons, consider a heavier coat for winter, such as something made from 32oz Melton wool or shearling. These can be worn with jeans, whipcord trousers, chambray shirts, chunky knits, and boots. Image
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Consider the difference between dress watches and sport watches. A dress watch is simple, often worn on a leather strap. A sport watch will be chunkier, often have various complications, and is typically worn on a metal bracelet. Sometimes a dressy outfit calls for a dress watch Image
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Some will complain that the outfits above were choosen by costumers, as they are from films. But even off-screen, Redford held to these practices. Here he is throughout his life as a dad hanging out with his kids. Image
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If you want to dress more like Redford, start with a navy sport coat, the most versatile tailored garment. It can be worn with jeans, tailored trousers, dress shirts, casual shirts, tie or no tie.

Gray herringbone tweed also works well if you mostly wear blue jeans. Image
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No matter his role or outfit, Redford also often sported a thin little chain, showing the veratility of this accessory. Image
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Rest in peace to a man who has given us much.

Consider watching some of his films this week. My favorites include Butch Cassidy and the Sundance Kid, All the President’s Men, Three Days of the Condor, The Sting, Jeremiah Johnson, and All Is Lost. Image

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More from @dieworkwear

Mar 21
In the 1950s, Irving Penn traveled across London, Paris, and NYC to take portraits of workers in their work clothes. These clothes at the time were not considered glamorous — they would not have shown up on fashion runways — but they demonstrate a simple aesthetic principle 🧵 Image
Consider these outfits. How do you feel about them? Are they charming? Repulsive? Stylish?

If you consider them charming and stylish, as I do, then ask yourself: what makes them charming and stylish? Why are you drawn to the outfits? Image
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As I've mentioned before, I think outfits look better when they have "shape and drape." By shape, I mean the outfit confers a distinctive silhouette. If these men took off their clothes, we can reliably guess their bodies would not be shaped like this: Image
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Read 14 tweets
Feb 20
Let me show you a wardrobe you can build with $1,700 🧵
NAVY SPORT COAT

If you're just dipping your toes into tailored clothing, start with a navy sport coat. This is something you can wear with a button-up shirt and pair of trousers, or something as casual as a t-shirt and some jeans. It's easily the most versatile jacket. Image
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Key is to get something with texture so it doesn't look like an orphaned suit jacket. Spier & Mackay has great semi-affordable tailoring. Their navy hopsack Moro is made from pure wool and a half-canvas to give it shape. Classic proportions and soft natural shoulder

Price: $358 Image
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Read 16 tweets
Feb 16
There's a pervasive belief that we no longer produce clothes in the United States. This is not true. In this thread, I will tell you about some great made-in-USA brands — some that run their own factories, while others are US brands contracting with US factories. 🧵 Image
I should first note this thread focuses on well-made, stylish clothes produced in ethical conditions. For me, producing in the US is not enough. It means nothing if the clothes are ugly, crappy, or produced in sweatshop conditions. My article for The Nation below. Image
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JEANS

Gustin produces MiUSA jeans using raw Japanese denim. "Raw" means the fabric hasn't been pre-distressed, allowing it to naturally fade with use, reflecting your actual body and lifestyle. I like their fuller 1968 Vintage Straight fit. They also do lots of other stuff. Image
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Read 17 tweets
Feb 7
Your suggestions are shit ass.

Let me tell you about backpacks. 🧵 Image
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Let's first establish good vs bad ways to think about style. The first pic is correct — style is a kind of social language and you have to figure out what type of person you are. The second pic is stupid bc it takes style as disconnected objects ("this is in" vs "this is out"). Image
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I should also note here that I'm only talking about style. I'm not here to argue with you about ergonomics, water bottle holders, or whether something accommodates your Dell laptop. I'm am talking about aesthetics.
Read 18 tweets
Feb 5
It's true that Canadian Prime Minister Mark Carney has a rounded back and forward pitched shoulders. But let me show you something. 🧵
Watch these two videos. Then answer these two questions:

— Which of the two men is better dressed?
— How does each come off?
I think Carney is better dressed, partly because his clothes fit better. Notice that his jacket collar always hugs his neck, while Pierre Poilievre's jacket collar never touches him.

Why do Poilievre's jackets fit like this? Image
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Read 11 tweets
Jan 18
The level of craftsmanship that goes into a lot of Japanese menswear simply doesn't exist in the United States. You can do this for many categories — suits, jeans, hats, etc.

In this thread, I will show you just one category: men's shoes 🧵
For this comparison, I will focus on Japanese bespoke shoemaking vs. US ready-to-wear. The level of bespoke craftsmanship shown here simply doesn't exist in the US, so a Japanese bespoke vs. US bespoke comparison would be unfair. US bespoke is mostly about orthopedic work.
So instead, I will focus on the best that the US has to offer: ready-to-wear Alden.

On a basic level, top-end Japanese shoes are better because they are handwelted, whereas Alden shoes are Goodyear welted. The first involves more handwork and can be resoled more often. Image
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Read 24 tweets

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