derek guy Profile picture
Apr 25 25 tweets 14 min read Read on X
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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In the early 20th century, a Norwegian man named Nils Tveranger traveled to the United States to learn the craft of shoemaking. While there, he was inspired by Indigenous North American moccasins, where the leather has been gathered around the toe, creating a ripple effect. Image
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Upon returning to Norway, he set up shop in Aurland, where he combined the Norwegian teser with the Indigenous North American shoemaking technique to create the Aurland moccasin. Aurland happened to be a popular destination at the time for European and North American fishermen. Image
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While in Aurland, these anglers picked up a pair of Tveranger's slip-ons and brought them home. With time, the style was copied. In 1936, G.H. Bass — then known for selling rugged boots to workers and outdoorsmen — debuted a slip-on they called the Weejun (short for Norwegian). Image
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Since Bass was primarily selling shoes to blue collar workers and outdoorsmen, they originally marketed these as something you could slip-on while "loafing in the field." Hence where we get the term loafer. But by the 1940s and 50s, students started wearing the Weejun. Image
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The loafer's popularity on campuses, especially elite institutions such as Harvard and Princeton, transformed this once rugged style derived from Norwegian peasant footwear into something more patrician. People typically wore them with "loafing" clothes (casualwear, sport coats) Image
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But soon enough, they seeped into business. Men started to team them with more refined clothes, such as business suits. Cary Grant even wore them with a tuxedo! Once Michael Jackson wore them in Thriller, they broke out of their patrician mold and took on new meaning (cool). Image
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Online, you'll often come across people directing you to buy a certain pair of loafers — GH Bass, Alden, Edward Green, etc.

I don't advocate for buying any particular thing. Rather, I encourage you to think about clothes in a certain way (one informed by history and culture).
The right pair of loafers for you — should they be right at all — depends on how small, subtle details fit into an overall aesthetic. We can think of this like how letters combine to form a word, which are then ordered in a certain way to form a sentence. This communicates ideas.
Sleek loafers made from a fine calfskin featuring a subtle apron and fine stitching will read "dressy," whereas a rounder toe loafer made from a thicker Chromexcel pull-up leather and feating contrast stitching, a thick lipped apron, and a stitched heel cup will read "casual." Image
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Even the vamp's length can change how a loafer reads. A loafer with a high vamp (coming up higher on your foot) will look dressier than a loafer with a low vamp, as it makes the foot look sleeker. Mark Cho of The Armoury explains here.

IG markchodotcom
These details determine how the loafers are best worn. A European suit will often demand slightly sleeker loafers because this forms a coherent silhouette and sense of formality. Something very casual, such as a sweater teamed with cords, looks better with causal loafers. Image
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Every pair of loafers will be made from a set of design decisions, which creates a certain "word" that's best used in a certain "sentence" (outfit). Leather, apron, stitching, coloring, vamp, sole, etc all combine towards this effect. Pictured below: dressy, casual, in-between. Image
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Compare these two loafers: Blackstock & Weber vs Edward Green. Both black loafers, but very different.

B&W: Grained leather, round toe, thicker sole, stitched heel cup. Casual.

EG: Smooth leather, sleeker shape, thinner sole, no heel stitching. Dressy. Image
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Blackstock & Weber makes the kind of loafers you'd wear with a casual or streetwear aesthetic. Edward Green makes the kind of loafers you'd wear with a finely tailored sport coat or suit. If you swap these shoes around, the effects would be very different (not necessarily wrong). Image
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Similarly, here are two pairs of black loafers from Carmina. They are identical in terms of quality. But the shape of the shoes and the design of the apron and heel cup make the first dressier, while the second is more casual. Image
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I should note that this thread assumes you already know some basic things. First, I assume you know how to spot quality in footwear. If you're not familiar with these basics, you can find a short explanation here:

Secondly, I assume you know that smooth calfskin is more formal than suede or pebble grain, and black is more formal than dark brown or mid-brown, which in turn are more formal than tan. These are among the most important elements in how a shoe "reads." Image
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Thirdly, I assume you know how shoes fit. Sleek shoes don't necessarily cramp the toes because men's dress shoes fit differently than sneakers. With sneakers, your toes reach the tip of the shoes. This is not so with dress shoes. Easy to see at a Japanese shoe fitting: Image
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The point of this thread is to move beyond the basics — how to determine quality, the way materials and color communicate formality, and how shoes should fit — and get into even finer details, such as stitching, heel cup, and apron (apron is the U-shape stitching below). Image
Which pair of loafers you should buy — again, assuming you should buy loafers at all — depends on how you like to dress. Are you mostly in shorts and t-shirts? Chinos and Shetland sweaters? Sport coats and suits? Do you prefer Italian or American style? Classic or contemporary? Image
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Hierarchies like these, along with declarations like "just go buy Alden," are not useful without a deeper understanding of the semiotical nature of clothing. To determine what kind of shoes (or clothes) to buy, you first have to have an idea of how you want to dress. Image
You can apply this approach to anything — finding the right jacket, jeans, T-shirt, etc. When repeated enough times, you will then have a coherent wardrobe. Here is a similar breakdown I recently did for chinos.

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More from @dieworkwear

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
Mar 21
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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As I've mentioned before, I think outfits look better when they have "shape and drape." By shape, I mean the outfit confers a distinctive silhouette. If these men took off their clothes, we can reliably guess their bodies would not be shaped like this: Image
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Read 14 tweets
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

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