derek guy Profile picture
Dec 11, 2023 14 tweets 7 min read Read on X
Let's talk about this because you may get invited to a party this holiday season that calls for "cocktail attire." What is cocktail attire? And how can you do it well? 🧵 Image
The term "cocktail attire" comes from a time when people went out and mingled at cocktail bars. In these physical spaces, there were two groups:

1) People just getting off of work
2) People on their way to another evening event, such as seeing a show Image
As such, cocktail attire refers to the things that people naturally wore during this period, given where they had just come from or where they were heading.

Office workers wore suits.

People on their way to an evening show, such as the opera, wore black tie.
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We don't really live in that world anymore, but if the invite says "cocktail attire," you will never be wrong showing up in a dark business suit or black tie.
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However, in doing so, you should aim to dress elegantly. That means wearing dress shoes instead of sneakers, black calfskin instead of brown suede, dark worsteds instead of rustic materials like brown corduroy. Maybe a bit of velvet. Think: fancy evening attire. Image
Many in these situations will feel tempted to ditch the tie, fearing that they'll look overdressed. If you are wearing a dark business suit, I encourage you to not do this. A dark business suit without a tie is like the night sky without stars. It looks sad and defeated. Image
If you're not going to wear a tie, I encourage you to put more thought into the rest of your outfit. Don't just ditch the tie and assume you look like George Clooney. One solution is to wear a thin merino turtleneck. This looks more thoughtful and stylish.
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Another easy solution is to wear a long-sleeve polo, but not like the ones you see at Lacoste or Fred Perry. You want a polo with a collar band, so that the collar stands up better. This will make it behave more like a dress shirt. @ProperCloth sells some nice MTM ones
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If a suit feels too formal, then try a sport coat. To me, sport coats lack the elegance of a suit, but they're still a great option for evening events. They are also easier to wear without a tie, as the whole ensemble now looks more casual. Image
Since this is an evening affair, consider how to make this look elegant. Something like this black/ white houndstooth from Besnard will look better at night than a brown sporting tweed (which, while wonderful, is better for the afternoon).
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If you have room in your wardrobe, you can also get a wool-mohair suit (60/40 blend is my preference). Mohair is a stiff, slippery fiber that has a slight sheen. I think it looks amazing under artificial light (dim bars and restaurants). Outfit can be conservative or wild
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An easy way to make an outfit look more chic in the evening is to rely on the same color and get your contrast from fiber, texture, or sheen. For example, a navy merino turtleneck can look amazing with a navy suit in hopsack or twill. Again, black shoes in the evening. Image
If you have the personality for it, you can also pull off something a little more colorful. My friend @toneloki73 here is wearing tartan trousers with a velvet jacket and red turtleneck. The whole outfit feels very celebratory, perfect for drinking cocktails. Image
The point here is to use history as a guide. Once you know the origins of cocktail attire, you can get a sense of how you should dress. Then use the parameters to express yourself. Aim to create an elegant party outfit. Make the night feel special.
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More from @dieworkwear

Sep 16
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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Read 19 tweets
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

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