derek guy Profile picture
Apr 21, 2025 21 tweets 12 min read Read on X
Rumors are going around that Pete Hegseth might be on his way out. I don’t know if that’s true, but just in case, I want to do a thread on his style. To me, Hegseth’s wardrobe reflects a common pitfall guys fall into when they first start caring about clothes. 🧵 Image
When men start dressing with more intention, they often fall into the trap of cranking every knob to 11—volume, gain, treble, bass. The thinking is: more = better. But like in music, maxing out every setting doesn’t lead to clarity—it leads to noise. Image
We see this in how Hegseth dresses. His belt buckle is USA. Pocket square is USA. Socks are USA. Open up his jacket and what do you see? USA. Image
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If there’s ever a chance to customize, he takes it—monogrammed shirt cuffs, contrast buttonholes, lapel pins galore. No flourish is left behind. Image
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With dark worsted pinstripe suits—the hallmark of conservative business dress—he skips the standard black oxfords and opts for bright tan shoes, simply because they catch the eye. And to drive it home, he throws on yellow socks to match his tie. Image
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The problem is that his clothes don't fit very well, and no amount of flourish or flair will hide this fact. He commonly wears clothes that are slightly too tight, sometimes resulting in a collar gap, as seen here

Trousers are a bit too low rise, sometimes revealing the flash or shirt fabric beneath the coat's buttoning point. Or, at times, his necktie. Image
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No matter your personal style, the most important elements of any outfit are fit and silhouette. Without those, everything else falls flat. Compare the more classic proportions on the left: longer jacket, wider shoulders, lower buttoning point, higher rise pants. Image
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Tailoring is meant to flatter the body, not reproduce its lines. On the left, the llama has a human-like shape, even though that’s not its natural build. Hegseth’s tailoring hews too close to his actual build, which makes things look a bit tight. Image
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Even in plain worsteds and without a single flourish, an outfit can look great if the tailoring is right. The first priority should always be fit and silhouette—everything else is secondary.

Examples below from Atelier Willow and Assisi, both in South Korea Image
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The second step is to think of your outfit as a whole—not just as a collection of pieces that excite you individually. Tan double monks might be fun, but they’re too casual for a charcoal pinstripe suit. Historically, tan shoes were for leisure, not business. Image
Business attire calls for "serious" shoes, typically lace-up oxfords in conservative colors such as black, dark brown, or mid-brown. They signal formality and restraint, which is exactly what conservative business dress is meant to convey. Image
It's admirable that Hegesth likes to wear his patriotism on his sleeve (or all over his body). But everything comes off very ham-handed and with no appreciation for this country's great clothing history. (Also, belt with black tie is .... very inelegant). Image
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I'd like to suggest some more sophisticated choices. Instead of an aggressively cut back spread collar (awful, tacky, too European) with a Windsor knot, he should honor this country's history with a button-down collar worn with a four-in-hand. Image
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The button-down, of course, is that style that Brooks Brothers introduced in the early 20th century and soon became a hallmark of classic American male dress. When cut properly, the collar points are long enough to create a soft, angelic roll. Can be worn with or without a tie. Image
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He should also ditch these suits. In the first pic, we see stiff, padded shoulders. In the second image, we see side vents (the flap at the back). And in the third pic we see machine-made pick stitching—the hard dimples along the lapel's edge. Image
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Those dimples are made to imitate the look of a handsewn European suit. Since the lapel is made from multiple layers of material, European tailors finish the edge with this gentle pick stitch. This results in soft dimples, not hard ones. Can look lovely if done well.
American clothiers typically finish their suit jackets and sport coats with a machine-sewn lapel, but they do a straight line so that there's no contrivance. See how the edge here doesn't have dimples—it's just a straight line of machine sewing. Doesn't try to imitate hand sewing Image
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Classic American tailoring is also distinguished by its soft shoulders, hook vent, and dartless front, which gives the jackets straighter sides. Image
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This is the style that carried American men from the hopping jazz clubs of the Roaring 20s through the Great Depression and onto campuses of a booming postwar America. The style suits any build, which is what makes it so democratic. Image
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As you start to dress with more intention, I encourage you to:

1) Prioritize fit and silhouette
2) Resist the temptation to turn every knob up
3) Think of dress as social language informed by history

IMO outfit on left is more sophisticated and American than one on the right. Image
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More from @dieworkwear

May 26
A lot of attention is paid to craft traditions in Western Europe and North America, such as handsewn Hermes leather goods and bespoke Savile Row suits. But the uneven focus leads some to believe that things made outside of these places are low quality.

This is not true. 🧵 Image
When I was on a menswear forum, there was a guy whose style I greatly admired. Like others on the forum, Niyi Okuboyejo loved men's tailoring. He had a technical understanding of how a jacket should hang from the shoulders. He also knew how to put things together in a classic way Image
At the same time, he also knew how to do things in his own voice and style, but in a way that looked good and not haphazard. Sometimes this was about adding a funky tie; other times, it was playing with materials and silhouette. All of these are still suits and sport coats! Image
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Read 17 tweets
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

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