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

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
Dec 18, 2025
A story I found about Haiti:

In 1999, a group of Haitians were tired of political disorder and dreamed of a better life in the United States. So they built a small, 23-foot boat by hand using pine trees, scrap wood, and used nails. They called the boat "Believe in God." 🧵 Image
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In a boat powered by nothing but a sail, they somehow made it from Tortuga Island to the Bahamas (about a 90 mile distance). Then from the Bahamas, they set sail again. But a few days and some hundred miles later, their makeshift boat began to sink. Image
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The men on the boat were so dehydrated this point, one slipped in and out of consciousness, unable to stand. They were all resigned to their death.

Luckily, they were rescued at the last minute by the US Coast Guard. Image
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Read 5 tweets

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