derek guy Profile picture
May 16, 2023 13 tweets 6 min read Read on X
HOW TO WEAR A SPORT COAT WITH JEANS

I see this sort of outfit all the time in the city, and it's pretty abysmal. So let's talk about better ways to wear sport coats with jeans 🧵
First, let's recognize why people are doing this. As dress norms have become more relaxed and casual, many men are trying to straddle the line between looking nice and looking overly dressed up. So they are trying to find ways to dress down their tailoring.
The problem with this outfit is that there's no harmony between the upper and lower halves. It's a business suit jacket with a white dress shirt up top, faded jeans and cowboy boots down bottom. This outfit looks like a giant mullet. Ron DeSantis is pictured we...
What you want to do is bridge the gap between the formality of the tailored jacket and the casualness of the jeans the best you can. This means paying attention to details and fine-tuning your outfit so there's less of a gap between the top and bottom halves of your fit. Photo of the knobs on an eq...
To start, know the difference between a suit jacket and a sport coat. A suit jacket can only be worn with jeans if it convincingly passes for a sport coat. You never want to wear a jacket that's obviously part of a suit with jeans.

Generally speaking, a suit jacket can pass for a sport coat if it's made from a more casual fabric, such as tweed, cotton, corduroy, or linen, rather than smooth worsted wools. It also helps to have casual details like patched pockets instead of flapped, and swelled edges Tweed swatches. Sport coats...Cut length of a navy worste...
You also want to wear a more casual shirt, such as a light blue oxford cloth button-down, rather than a dressier spread collar shirt made from white poplin

Despite what u see in fashion ads, u should also forgo the tie when wearing jeans. Combining the two often looks contrived. A man in a light blue oxfor...A man in a spread collar wh...
Next is the cut. Jeans should never fit like tailored trousers, but you also want some harmony between jacket and pants in terms of silhouette. That means avoiding overly slim or low-rise jeans. Aim for a slim-straight leg with moderate rise. A man wears a navy blazer w...
Levis Vintage Clothing's 1947 501s, Orslow 107 and 105, 3sixteen CT-100x, Blackhorse Lane NW3, Full Count 0105, Warehouse 1002, The Armoury, and Drake's are all good models to check out.

While not an ironclad rule, it's also generally easier to wear dark jeans with tailoring. Jason Jules models a tweed ...
Finally, avoid dress sneakers. Go for a classic, but slightly more casual version of a traditional shoe. Suede chukkas and loafers work well. If you must wear sneakers, do a simple all-white shoe, not some wingtip with a sneaker sole.
When put together, you get something like this: a slightly more casual version of a sport coat paired with a casual shirt and classic, but casual shoes. There is coherence between the jacket and pant silhouette. Peter wears a summer sport ...Mark wear a tan linen sport...Simon waers a grey tweed wi...David wears a brown tweed s...
The idea is to avoid all the mistakes you see here: obvious suit jacket + white dress shirt + red tie + low rise, skinny jeans + athletic or dress sneakers. There's no coherence between any of the pieces. Top half is too formal for bottom half. Matt Gaetz wears a grey sui...
Personally, I think most guys should just avoid the combo, as it can take a while to develop your eye for what works. Most guys are better off buying sport coats, not repurposing suit jackets as sport coats, and wearing these with traditional tailored trousers and dress shoes. A man wears a navy sport co...

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More from @dieworkwear

Sep 26
Let me tell you a beautiful story about this couch. 🧵

IG msviciousdesign
Some will recognize these motifs as Mughal paintings, which flourished on the Indian subcontinent sometime between the 16th and 18th century. But menswear nerds will recognize them as something else: Drake's of London.

Left: thrifted couch
Right: Drake's of London scarf Image
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Drake's of London is a menswear label that started in the 1970s, initially with men's accessories, but having since grown to a full line of apparel. They are known for many things, but this print is perhaps their most famous. It appears on scarves, pocket squares, and even ties. Image
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Read 24 tweets
Sep 16
Style lessons from Robert Redford, one of the most stylish men in the last century. 🧵 Image
A tailored jacket continues to be one of the most flattering things you can wear. However, for it to look good, it has to fit right. That means a jacket that bisects you halfway from your collar to the floor when you're in heeled shoes. Also trouser + suit jacket silhouette flows Image
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It also helps to know how to use this visual language, especially with regard to ideas about formality. For instance, a dark business suit cries out for a tie. If you don't want to wear a tie, try a more casual garment, like a sport coat. Image
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Read 19 tweets
Sep 15
Someone yesterday asked me why someone would ask a tailor to make a polo coat in such a way to imitate the look of a machine-made garment.

The answer holds a beautifully little story about the difference between European and American style. 🧵
Let's start with a test. Here are two tan polo coats. One is machine-made. The other is handmade. Can you guess which is which?

Please answer before moving on. Then you can scroll through the answers to see whether most people got it right. Image
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The first coat is machine-made. It's from an American ready-to-wear company called J. Press. The second is handmade. It's from a London bespoke tailoring house called Anderson & Sheppard.

You can spot the difference by how the edges are finished. Image
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Read 19 tweets
Sep 15
I disagree that Obama wore "slick suits."

Let me tell you about Obama's tailoring. 🧵
I've seen people here suggest Obama was a stylish president. I couldn't disagree more. Outfits like these read better in 2025, but during the slim-fit, Euro style craze of his presidency, Obama was routinely panned for his "frumpy dad style." See Vanity Fair. Image
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His style transformation really came post-presidency. I suspect, but don't have proof, that this is partly the influence of his wife, who is quite stylish. Even his suits look better now. See clean shoulder line + shirt collar points reaching lapels + nice four-in-hand dimple. Image
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Read 16 tweets
Sep 9
Although it's rarely expressed in outright terms, people often use a very simple heuristic when solving fashion problems: they wish to look rich, which is often disguised as "respectable."

I will show you why this rarely leads to good outfits. 🧵 Image
In 1902, German sociologist Georg Simmel neatly summed up fashion in an essay titled "On Fashion." Fashion, he asserted was simply a game of imitation in which people copy their "social betters." This causes the upper classes to move on, so as to distinguish themselves. Image
He was right. And his theory explains why Edward VIII, the Duke of Windsor, was the most influential menswear figure in the early 20th century. By virtue of his position and taste, he popularized soft collars, belted trousers, cuffs, Fair Isle sweaters, and all sorts of things. Image
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Read 25 tweets
Sep 6
It's funny to see people imbue traditional men's tailoring with their own prejudices. They assume every man who wore a suit in the far past must be a staunch conservative like them. The truth is much more complicated. 🧵
This bias, of course, stems out of the 1960s and 70s, from which many of our contemporary politics also spring. I don't need to belabor this point because you already know it. The framing is neatly summed up in this Mad Men scene — the rag tag hippie vs man in a suit.
Thus, people assume that men in suits must always be part of the conservative establishment. But this was not always so. The suit was once a working man's garment. When Keir Hardie, founder of the Labour Party, arrived for his first day in Parliament, he wore a suit. Image
Read 17 tweets

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