derek guy Profile picture
Nov 28, 2023 19 tweets 9 min read Read on X
Someone asked, "What's up with the rolled pant legs in each of these outfits?" So here's a thread on the history behind men cuffing pants, the meaning of cuffs, and how to think about when you might want to cuff your pants. This thread covers tailored trousers and jeans. 🧵
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As a consequence of the Second British Empire, much of traditional Western men's dress comes from England. There, men of means had wardrobes cleaved between country and city. County clothes were for sport. City clothes were for business. Hence the phrase, "no brown in town."
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No one really knows when British men started cuffing their pants, as much of menswear history is muddled with lore. But one story suggests it started with King Edward VII, who turned up his pants to prevent the hems from getting dirty in the mud or rain. Image
Regardless of who started doing it, the detail was considered casual. It was more often seen on country suits worn for sport while trudging through the muddy countryside than on slick worsteds worn for business around London's streets. Image
This was until Edward VIII came along. By all accounts, Edward VIII (also known as the Duke of Windsor) was a blithering idiot, but he was also the single most influential figure in men's fashion during the 20th century. When he wore something, others followed. Image
The Duke loved breaking menswear rules and making his outfits more casual (anyone who laments the casualization of men's style in the modern era is unfamiliar with history). The Duke's father, George V, often criticized him for wearing turn-ups while inspecting troops. Image
The Duke didn't care and made cuffs a style signature. Soon, everyone was doing it, including the future members of the Royal family. It also became common to see them on "city suits" made by some of Savile Row's most traditional tailors.
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Americans have always been about making clothes a little more casual. We popularized the single-breasted two-piece suit, the lounge suit as business daywear, penny and tassel loafers with suits, oxford button-down collars, seersucker, patchwork madras, 3 roll 2 sack jackets, etc
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So it's no surprise that Americans adopted cuffs. Flat-front pants with cuffed hems were a signature of a style imported from Britain, championed by Brooks Brothers, and spread across the US through Ivy clothiers. Note RFK's cuffed hem and 2 button sleeve (both casual details) Image
There is a somewhat concurrent history here with jeans. In the early days, jeans were made from unsanforized denim, which is to say that the fabric was not pre-shrunk. This meant that the jeans shrank a little over time with each wash. Image
To prevent jeans from being too short ("high waters"), people cuffed them so the length was adjustable.

Over time, jean production became modernized. Denim was more commonly sanforized. Shuttle looms were replaced by power looms. There was also pre-washing and -distressing. Image
But there were also people—many in Japan—who loved those original pre-1970s Levis jeans. Things made from raw, unsanforized denim that had been woven on old shuttle looms. Collectors looked for a "Big E" on the Levis tab and a selvedge stripe on the inside leg.
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As the cost of vintage jeans went up, people started to make new jeans using these old methods. That's where you get shops such as @selfedge (my favorite denim store). You may ask, "how can jeans cost $300+?" It's because these are made in small batches using niche methods.
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For people who love that vintage look, they may turn up the cuffs to show off the selvedge stripe (pic 1). This admittedly used to be a rarer detail 10-20 years ago than it is today (but it's still cool, IMO). Others wear cuffs bc they take inspiration from vintage looks (pic 2)
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So, how should you think about cuffs in relation to your outfits?

For trousers, adding a cuff can help them hang better, as you have a bit of weight at the end of your pants. They are fine on anything except tuxedos (as this is a casual detail).
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To me, pleated pants almost cry out for cuffs. Flat fronts can go either way (although the Ivy thing to do is cuff). Anything between 1.5" and 2" is fine, although narrow pant legs should be on the smaller side. I like my friend Dick Carroll's guide here (IG dick.carroll) Image
For denim, I think cuffs are good if the outfit feels classic or vintage-inspired. For a more contemporary outfit, such as what you see at Lemaire or Margiela, I think a plain hem or even a stacked leg looks better.
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A graphic designer friend once put it in very useful terms: you can think of cuffs like the serif on a font. A serif can make typography look more traditional, while a sans-serif looks more modern. So traditional tailoring? Cuff. More modern look? Plain hem.
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If you just bought a new pair of pants and you're unsure whether you should get them finished with a cuff or a plain hem, I recommend starting with a cuff. You can always take cuffs out, but you can't put them in. Image

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More from @dieworkwear

May 11
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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There are a few reasons why most outfits look bad with these sorts of socks. First, most men are not at that senior age where these socks become charming.

Second, most of these socks look like something you acquire by sending in a proof-of-purchase from a cereal box. Image
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Read 17 tweets
May 1
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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White tie is true formalwear. It differs from black tie primarily in how it requires a long tailcoat (black tie originated when men cut the tails off their coats to create a more casual garment for dinner). Also requires a white waistcoat, white tie, and wing collar. Image
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Read 17 tweets
Apr 30
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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Taillour

In bespoke tailoring, there's a generally accepted rule that most clients would do well to observe: choose a company based on their house style and stay close to it. The term "house style" refers to the tailor's established methods, which combine to create clothes with a distinguishable fit and feel. Just as you wouldn't order burritos from a ramen chef, you shouldn't ask an English tailor for an Italian jacket (or vice versa).

Taillour is one of the few exceptions. Co-founder and head cutter Fred Nieddu has worked in the bespoke tailoring industry for decades, cutting for firms such as Thom Sweeney and even teaching pattern drafting courses at the London College of Fashion. A good percentage of his current workload involves making clothes for films and TV shows. In fact, you may have seen his creations. He made all the menswear for the Netflix series The Crown, the suits in the film The Phoenician Scheme, and one of the colorful costumes for Wonka. Given this experience, he's more flexible than most tailors regarding what he's willing and able to make.

Still, I think it's always a good idea to stay close to the house style. I think of Taillour's house style as very soft but architectural in its lines. Nieddu uses a full body canvas and only a bit of laptair near the wearer's collar bone to prevent the jacket from sinking. The shoulders are minimally padded, giving the garments a very light feel. While Neapolitan tailors are known for a similar construction, Taillour's jackets have a bit more room and shape. The shoulder line is very straight, and the chest is slightly full. When combined with those characteristically straight lapels and larger jacket collar, I find Taillour's jackets have an angular appearance reminiscent of Apparel Arts drawings.

Consider Nieddu if you want a tailor who's a bit more flexible in terms of what they're willing to make (although, again, I recommend tweaking at the margins, not bringing in a photo of something and asking for it to be copied). He has also made clothes for women, which will be useful if you're looking for someone who can make a women's suit, sport coat, or overcoat.Image
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Read 4 tweets
Apr 25
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
As always, it's helpful to start at the beginning.

There are a few origin stories for loafers, but most lead back to Norway. If menswear lore is to be believed, then the penny loafer comes from a simple slip-on shoe known as the teser, which was once worn by Norwegian peasants. Image
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Read 25 tweets
Apr 15
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.
During the 1898 Spanish-American War, US troops stationed in the Philippines wore sand-colored pants made from a heavy cotton twill woven in China. Since the Philippines had been under Spanish colonial rule at this time, the locals call these "pantalones chinos" (Chinese pants). Image
Read 23 tweets
Apr 4
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
Of course, you can always celebrate in the same clothes you wear to bed. But IMO, this diminishes the moment. Thus, it's nice to special outfits for "It," even if you don't wear them all the time. It's similar to toasting a special glass of champagne and drinking water. Image
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Read 14 tweets

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