Hello again,
As someone who works in media I often get asked what I think about AI and how it will impact the industry. I honestly don’t spend a lot of time thinking about it, since the industry is doomed anyway and my own interactions with AI leave me feeling so dead inside that I don’t consider it very threatening.
But if I had to answer: I don’t think AI will be able to do things like write a deeply reported magazine feature, author a Best Picture-winning screenplay, or produce a work of art that touches you at your soul. But could AI be a reliable source of decent menswear advice?
Yes, it probably could.
So I decided to put that question to the test this week. I ran a few queries FOB readers have sent me recently by ChatGPT and compared the answers to my own recommendations. What I found will shock you. (Not really.)
First, I asked ChatGPT to write an intro to this article:
In the ever-evolving world of menswear, the quest for style often leads to a myriad of opinions and recommendations. As artificial intelligence steps into the realm of fashion advice, it raises the question: can a machine truly understand the nuances of personal style as well as a seasoned human menswear writer?
In this article, we will explore the contrasting approaches to men’s fashion, comparing AI-generated insights with the curated advice of a human expert. From formal occasions to casual wear, we’ll delve into how both perspectives navigate trends, fit, and individuality, helping you make informed choices that elevate your wardrobe. Join us as we bridge the gap between technology and tradition in the pursuit of sartorial excellence.
ChatGPT vs. Front of Book
Q: I need a suit for a wedding in two weeks. Recommendations? Around $600-$900 seems reasonable as I won’t wear it often.
ChatGPT:
Here are a few recommendations for suits in that price range that are stylish and suitable for a wedding:
1. Indochino: They offer custom suits that start around $399. You can choose your fabric, style, and fit, making it a great option if you want something tailored just for you.
2. SuitSupply: Known for their quality and fit, SuitSupply has a variety of suits in the $500-$800 range. Their styles are modern and versatile, perfect for weddings and other occasions.
3. J.Crew: Their Ludlow suit is a classic option that typically falls within your budget. You can often find sales or promotions, which can bring it closer to your price range.
4. Bonobos: They offer well-fitting suits that come in a range of sizes and styles. Prices usually start around $500, and they have a good selection of colors and patterns.
5. Macy’s or Nordstrom: Both department stores carry a range of brands at different price points. Look for brands like Calvin Klein, Kenneth Cole, or Tommy Hilfiger; you can often find quality suits within your budget.
Make sure to check for any upcoming sales, and if you have time, getting it tailored will make a big difference in fit!
Front of Book:
First, I was pleased to see ChatGPT using the Oxford comma. Second, the answer got me bit worried ChatGPT was coming for me because my recommendation was actually on the list: SuitSupply. I’ll caveat that by saying that my overall recommendation to avoid the situation of having to find a suit with such short notice. Instead, invest in a bespoke or made-to-order suit from a reputable suit maker (for me, that means J. Mueser, P. Johnson, Husbands, or something from The Armoury, for example).
But for many people, that will be too much money for an outfit you won’t wear that often. So for something at a lower price point that you can try on, buy, and alter in less than two weeks, I would go with SuitSupply.
SuitSupply has evolved in recent years from the skinny, early aughts kind of suit (like Indochino and Bonobos still does) into a more modern, fashion-forward brand. The fits are relaxed, with wider lapels, longer jackets, varied fabrics, and complementary polos, knitwear, and sweaters. When I visited the store this summer I was astonished with how much the suiting styles reminded of me of P. Johnson. (A few weeks later I spoke with a P. Johnson employee who told me that SuitSupply orders suits from P. Johnson and has them shipped to SuitSupply’s Soho store, presumably for inspiration.)
When my friend reached out about the wedding suit, I specifically recommended the all season Dark Brown Tailored Fit Milano Suit with a double breasted jacket for $749 (above). That’s a nice price point for a standout and versatile suit that will delivered right to your door. Adjustments can be done in-store and are wedding-ready in a few days.
Q. I need two new pairs of men’s pants, one fashion-forward and fun, one more classic and formal/preppy. I don’t want to spend more than $400 total. Where should I get them?
Chat GPT:
Here are some great options for both fashion-forward and classic pants within your budget:
Fashion-Forward Pair
1. ASOS: They have a wide selection of trendy and unique pants, from colorful chinos to patterned trousers. You can usually find something fun for around $50-$100.
2. Zara: Known for their stylish and modern pieces, Zara often has bold designs and prints. Expect to spend around $70-$120 for a pair of trendy pants.
Classic and Formal/Preppy Pair
1. Banana Republic: Their chinos or dress pants offer a polished look. You can often find good options for $100-$150, especially during sales.
2. J.Crew: The Dock chinos or other tailored pants are classic and preppy. Prices typically range from $98 to $150, and they have frequent sales.
With careful selection, you should be able to get both pairs within your $400 budget!
Front of Book:
One advantage I have as a human being is I can think outside the parameters of the question. My advice to my friend was that he should consider spending over his budget on higher quality pants that will last longer. My experience has been that paying more for an item from a great brand is an overall better investment that will save you money in the long run.

For dressier pants, I suggested Rota Pantaloni from Italy. All Rota does is make pants and they’ve been doing it since 1962. Their selection ranges from flat front to pleated to easy pants, in fabrics including wool, cashmere, silk, and linen. The site No Man Walks Alone always has an evolving selection of Rota pants (I especially love the Brooklyn double-pleat high-rise wide fit trousers in chocolate brown Brisbane Moss cotton corduroy).
For a more casual pant, I would go with Rubato. Although I’ve never owned a pair myself, menswear nerds are crazy about this brand, especially the made-in-Japan Officer’s Chino. Buck Mason also makes a nice chino at a lower price, and The Armoury by Ring Jacket’s Cotton Army Chino also comes highly recommended.
Q: I would love your take on how to dress formally but stylishly in Hawaii. I’m starting a research job on Tuesday for the City of Honolulu and need to dress somewhat formally, but to be honest I hate the way most of the formal dressers look here. I’m so used to shorts and a T-shirt and flip flops. Now I have to wear an Aloha shirt every day. I guess a linen shirt works too. I'm 5’11”, 155 lbs., with a lean, surfer’s build. What do you recommend?
Chat GPT:
Dressing formally yet stylishly in Hawaii can be a fun challenge! Here are some tips and outfit ideas that will keep you looking polished while still feeling comfortable in the warm climate:
Aloha Shirts
Opt for Tailored Cuts: Look for Aloha shirts that have a tailored fit rather than a boxy one. Brands like Tori Richard or Kahala often have options that look sharp.
Subtle Patterns: Consider shirts with more muted or sophisticated patterns. Solid colors or smaller prints can look more polished than large, vibrant designs.
Linen Shirts
Lightweight and Breathable: A high-quality linen shirt in a light color can be both comfortable and stylish. Look for options from brands like Everlane or Uniqlo.
Collared Styles: A button-down collar adds a touch of formality. Pair it with nice chinos for a smart-casual look.
Trousers
Chinos or Dress Pants: Lightweight chinos in a neutral color (like khaki, navy, or gray) can pair well with both Aloha and linen shirts. Brands like Bonobos or Dockers offer great options.
Tailored Shorts: If the dress code allows, you might consider tailored shorts in a smart fabric. Look for options with a neat hem and a polished look.
Footwear
Loafers or Casual Shoes: Instead of flip-flops, opt for loafers or stylish sneakers. Brands like Clarks or Sperry offer comfortable yet polished options.
Accessories
Lightweight Blazer: If needed, a lightweight blazer can elevate your look. Choose one in a breathable fabric.
Minimalist Watch: A simple watch can add a touch of class without being overly formal.
Final Tips
Color Palette: Stick to a cohesive color palette to make mixing and matching easier.
Fit is Key: Ensure everything fits well, as good fit can elevate even the most casual of styles.
With these pieces, you can create a wardrobe that respects the local culture while keeping your personal style intact. Enjoy your new job in Honolulu!
Front of Book:
Linen, linen, linen.
Linen shirts, a linen blazer, linen pants. Lightweight cotton pants are fine, too, even a light summer wool. For me, this is the platonic fit for dressing well in hot, humid climates, and everything should flow from it:
A well-fitting linen shirt tucked into an elegant, clean pair of chinos or summer dress pants with a few accessories and you’re in business. Slowear makes excellent linen shirts with enough heft in the fabric to wear to work. Rubato, mentioned above, has lovely ivory trousers, and depending on the season James Perse has versatile, lightweight pants that will work for a casual office environment. For shoes, go with a casual loafer, moccasin, or Belgian, like these from Morjas, or a pair of huaraches, if the workplace allows it.
As for the Aloha shirt—if everyone else is wearing one, be different and leave it at home. You’re not from Hawaii, after all, so you don’t have to pretend to be Hawaiian. If all else fails, let Magnum be your guide:
Thanks for your input ChatGPT, and thanks for reading everyone. I’ll be back next week with more from Paris and some of my favorite fall items.
Mitch
Question? Comment? Suggestion? Caught a typo? Email me at mitch.moxley@gmail.com