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Sep 16 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

Sep 15
Someone yesterday asked me why someone would ask a tailor to make a polo coat in such a way to imitate the look of a machine-made garment.

The answer holds a beautifully little story about the difference between European and American style. 🧵
Let's start with a test. Here are two tan polo coats. One is machine-made. The other is handmade. Can you guess which is which?

Please answer before moving on. Then you can scroll through the answers to see whether most people got it right. Image
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The first coat is machine-made. It's from an American ready-to-wear company called J. Press. The second is handmade. It's from a London bespoke tailoring house called Anderson & Sheppard.

You can spot the difference by how the edges are finished. Image
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Read 19 tweets
Sep 15
I disagree that Obama wore "slick suits."

Let me tell you about Obama's tailoring. 🧵
I've seen people here suggest Obama was a stylish president. I couldn't disagree more. Outfits like these read better in 2025, but during the slim-fit, Euro style craze of his presidency, Obama was routinely panned for his "frumpy dad style." See Vanity Fair. Image
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His style transformation really came post-presidency. I suspect, but don't have proof, that this is partly the influence of his wife, who is quite stylish. Even his suits look better now. See clean shoulder line + shirt collar points reaching lapels + nice four-in-hand dimple. Image
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Read 16 tweets
Sep 9
Although it's rarely expressed in outright terms, people often use a very simple heuristic when solving fashion problems: they wish to look rich, which is often disguised as "respectable."

I will show you why this rarely leads to good outfits. 🧵 Image
In 1902, German sociologist Georg Simmel neatly summed up fashion in an essay titled "On Fashion." Fashion, he asserted was simply a game of imitation in which people copy their "social betters." This causes the upper classes to move on, so as to distinguish themselves. Image
He was right. And his theory explains why Edward VIII, the Duke of Windsor, was the most influential menswear figure in the early 20th century. By virtue of his position and taste, he popularized soft collars, belted trousers, cuffs, Fair Isle sweaters, and all sorts of things. Image
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Read 25 tweets
Sep 6
It's funny to see people imbue traditional men's tailoring with their own prejudices. They assume every man who wore a suit in the far past must be a staunch conservative like them. The truth is much more complicated. 🧵
This bias, of course, stems out of the 1960s and 70s, from which many of our contemporary politics also spring. I don't need to belabor this point because you already know it. The framing is neatly summed up in this Mad Men scene — the rag tag hippie vs man in a suit.
Thus, people assume that men in suits must always be part of the conservative establishment. But this was not always so. The suit was once a working man's garment. When Keir Hardie, founder of the Labour Party, arrived for his first day in Parliament, he wore a suit. Image
Read 17 tweets
Sep 6
Which of these two jackets do you prefer?

There's no "right" or "wrong" answer here, so feel free to go with your gut. I will then give you my views below. 🧵 Image
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In men's tailoring, the area below the jacket's buttoning point is colloquially known as the "quarters" among menswear enthusiasts. Or the "front edge" by actual tailors. These terms refer to the edge of the coat, connecting to lapels. Image
Some suit jackets have very closed quarters, such as you see on the left. In this way, the jacket forms a Y-shaped silhouette.

Other suits have open quarters, such that the front edge sweeps back on the hips, as you see on the right. This forms an X-shaped silhouette. Image
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Read 6 tweets
Aug 30
Here are ways to dress up in the summer if you wear menswear. 🧵
We will start with the most formal and work our way down, so that you can adjust things in ways that make sense for you.

The first and most obvious choice is to wear a soft-shouldered suit rendered in a material such as linen or seersucker. Seersucker can even be tonal (pic 4) Image
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However, when it comes to dressing for the heat, it's important to remember that the fabric's weight and weave are more important than fiber. A 10oz tropical wool — known for its open weave — will wear cooler than a densely woven 14 oz linen because it allows air to pass through Image
Read 23 tweets

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