derek guy Profile picture
Menswear writer. Editor at @putthison. Bylines at The New York Times, The Financial Times, Politico, Esquire, and Mr. Porter
May 11 17 tweets 10 min read
I think "fun socks" should be used judiciously, as a lot of what's worn today feels more childish than whimsical. IMO, most men should avoid them entirely.

But if you insist on wearing them, here are some suggestions on how to make them look less bad. 🧵 Any time this topic comes up, people invariably bring up George HW Bush, who was known to wear fun socks later in life. While I wasn't a fan of those socks, I agree that Bush was well-dressed. I also think when you reach a certain age, you have license to wear whatever you want Image
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May 1 17 tweets 13 min read
I respectfully disagree. This sort of outfit can be beautiful, but it has to be done well.

IMO, the problem with Vance's outfit — along with many others — is that the work has been influenced by fashion designers, rather than tailors.

Let me show you. 🧵 Most people think of black tie as the most formal kind of menswear, but technically speaking, it's semi-formal evening attire. Historically, men wore this kind of outfit to dinner or evening shows, such as going to the opera or ballet. Or celebrations such as NYE parties. Image
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Apr 30 4 tweets 8 min read
If you're interested in bespoke tailoring and based in the United States, I have some trunk show announcements to share with you. Since Twitter recently changed their formatting options, I will be doing this as a thread. 🧵 Matthew Gonzalez

There's a long history of cross-border influence and immigration in tailoring, but as far as I know, Matthew Gonzalez is the first American to operate under his own banner on Savile Row. Born and raised in Southern California, he moved to London about twenty years ago to pursue a degree in bespoke tailoring from the London College of Fashion. Thereafter, he climbed the ranks — moving from undercutter at Thom Sweeney to cutter at Dunhill and eventually Huntsman, where he achieved his longtime goal of cutting on Savile Row.

Today, he runs his own firm, where he merges his California sensibility with his training in British bespoke craftsmanship. He recently told me he admires a photo of JFK staring out of a window. The President dressed in a dark worsted suit, white button-up shirt, and dark silk necktie, but everything about the photo looks very casual and relaxed. This, he told me, is what American style means to him.

Gonzalez cuts suits and sport coats inspired by that mid-century American tailoring, although he's adamant about not wanting the clothes to look like historical costumes. Thus, while the jackets have a soft, natural shoulder line, he sticks with front darts and prefers side vents (rather than the dartless front and hook vent characteristic of Ivy Style). The lapels have a moderate width and minimal belly (the curve sometimes distinguishing an older style of British tailoring). The garments are designed so they can be teamed with a dress shirt and tie, or something more casual such as a chambray button-up.

Given Gonzalez's penchant for slightly more relaxed, casual attire, it's no surprise that he also offers made-to-measure suede jackets, wool-cashmere shawl collar cardigans, and denim Western shirts (made without the contrast stitching, so they look more at home with tailoring). He's also one of the few bespoke tailors I've met who "gets it" when it comes to the polo coat, arguably the most iconic of American overcoat styles. Gonzalez tells me he thinks a polo coat should have letter box patch pockets, a half belt, gauntlet cuffs, an inverted back pleat, and a center button vent. But crucially, he also thinks the split-sleeves should be made with a lapped seam. To my eye, this makes the garment more casual and sporty—truer to its original roots—and allows the tailor to shape the sleevehead.

Consider Gonzalez if you share the same sensibilities: a love for classic American tailoring, but a suspicion of styles that are too anachronistic, and a bias towards clothes that feel more relaxed and casual. The point about Gonzalez using a split-sleeve with a lapped seam demonstrates that he takes care of details that may not occur to a client, but will be appreciated years down the road.Image
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Apr 25 25 tweets 14 min read
Summer is around the corner and soon you'll read a bunch of tweets about how every man should have a pair of loafers.

I don't think anyone needs anything, but if you're shopping for a pair, let me show you how to think about loafers. This applies to any wardrobe item. 🧵 Image When it comes to choosing loafers, a simple answer will go something like this: "Such-and-such brand makes the best pairs." Or "Here's a hierarchy of loafers." IMO, such approaches are reductive and often devolve into trend or status pursuits.

Let me show you another approach. Image
Apr 15 23 tweets 13 min read
Someone asked if I could tell them where to buy a pair of good chinos. In this thread, I will tell you, but my answer is not simple. On the upside, I think this is a better approach when shopping for clothes and you can apply it to any kind of item. 🧵 Image A simple answer will go something like this: "Such-and-such makes the highest quality chinos." Or "this brand provides the best value." While potentially useful in some respects, I don't think this gives you the fullest picture.

Instead, let's start at the beginning.
Apr 4 14 tweets 8 min read
One day, "It" will happen, by which I mean sudden and unexpected news that you want to celebrate. In such cases, you will want the right outfit. 🧵 What do I mean by "It?" I mean that joyous moments are not always something you can plan for. Perhaps you received a pay raise or got accepted at a waitlisted school. Perhaps a loved one is now cancer-free. Such moments can be sudden and unexpected — and you want to be prepared. Image
Mar 21 14 tweets 10 min read
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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Feb 20 16 tweets 10 min read
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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Feb 16 17 tweets 10 min read
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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Feb 7 18 tweets 12 min read
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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Feb 5 11 tweets 5 min read
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?
Jan 18 24 tweets 13 min read
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.
Dec 18, 2025 5 tweets 4 min read
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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Dec 1, 2025 18 tweets 12 min read
After this post went viral, I called Caroline Groves, a world-class bespoke shoemaker, to discuss how women's shoes are made. I normally don't talk about womenswear, but I found the information interesting, so I thought I would share what I learned here. 🧵 First, who is Caroline Groves?

Footwear is broadly broken into two categories: bespoke and ready-to-wear. In London, bespoke makers, including those for women, are largely focused on traditional styles, such as wingtip derbies and loafers. Emiko Matsuda is great for this. Image
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Nov 29, 2025 24 tweets 15 min read
Earlier today, Roger Stone announced his partnership with a menswear company, where together they've released a collection of tailored clothing items.

Here is my review of those pieces. 🧵 Image The line is mostly comprised of suits and sport coats, supplemented with dress shirts and one pair of odd trousers (tailor-speak for a pair of pants made without a matching jacket). Suits start at $1,540; sport coats are $1,150. One suit is $5,400 bc it's made from Scabal fabric Image
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Nov 24, 2025 20 tweets 11 min read
Here is a guide breaking down what goes into quality men's footwear. This is focused on men's shoes, as women's shoes, depending on the style, will have different construction techniques and thus standards. 🧵 First, let's set a standard. What does it mean for a pair of shoes to be "good quality?" In this thread, I define that standard to be two things:

— Do the shoes age well?
— Can they be easily repaired?

In short, you should want and be able to wear the shoes for a long time. Image
Nov 23, 2025 8 tweets 7 min read
When I was on a menswear forum, one of my most controversial opinions was that certain coats look better when they're worn open, while others look better when they're closed.

For instance, which of these two outfits look better to you? 🧵 Image
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If you shop for an overcoat today, there's a good chance you'll land on a single breasted. As suits and sport coats have receded from daily life, the types of outerwear that men historically wore with them have also slowly disappeared. Image
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Nov 22, 2025 4 tweets 3 min read
The reason why this looks off is bc the coat is built from many layers of material — haircloth, canvas, and padding — which sits on top of another jacket with similar structure. This can make you look a bit like a linebacker. If you find this to be the case, switch to a raglan 🧵 A raglan is defined by its sleeve construction. Most coats have a set-in sleeve, which is to say the sleeve attached to a vertical armhole, much like a shirt. A raglan, by contrast, has a diagonal seam running from the neck to armpit. Historically, this was put on raincoats. Image
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Nov 22, 2025 9 tweets 7 min read
I disagree.

Instead of thinking there's "the best watch," I recommend thinking about your wardrobe and lifestyle. 🧵 If you mainly wear suits and sport coats, then you will want a simple dress watch on a leather strap. Remember that the spirit here is elegance, so the watch should also be elegant. Certain dress chronos can also work, such as the Vacheron Constantin 4072 in pic 4 Image
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Nov 12, 2025 25 tweets 12 min read
Let me show you the difference between a $40 hoodie and a ~$100 hoodie. 🧵 Within the part of the menswear industry that I operate in, Roopa Knitting Mills is widely regarded as one of the best hoodie manufacturers. Founded in 1991 by an Indian immigrant named Nat Thakkar, they do every production step after yarn spinning in Ontario, Canada. Image
Nov 3, 2025 15 tweets 7 min read
Not true. Both Joe Biden and Gavin Newsom wear ready-to-wear or factor-made clothes produced on a block pattern.

I'll show you how I know. 🧵 Image First, what do you notice about this jacket? Image