This thread argues that many clothing rules are based on prejudice or lack of style knowledge. It explains that items like pocket squares, cargo shorts, jewelry, sneakers with suits, and even women’s fashion can be styled well if you know how. Fashion isn’t about strict rules but about having fun and expressing yourself, regardless of what some lists say.
This list is terrible. When people say that men should never wear a particular item of clothing, their view is often shaped by fear and prejudice. It's also often an issue of them not knowing how to style something. I will run through some examples on this list. 🧵
@JohnLeFevre
Here are 40 things a man should never wear:
1. Flips flops unless you’re near a pool or beach.
2. Flamboyant pocket squares. All it says is you pay $1,200 a month for a car you can’t afford.
3. Statement socks. They don’t give you personality or style.
Pocket squares add visual interest to tailored jackets, which is especially useful if you don't wear ties. The best ones have complex, nonrepeating patterns because you can twist them to show specific colors. Always stuff; don't fold them like origami birds.
Cargo Shorts
Yes, there are bad cargo shorts, but there are bad versions of everything. Frat boy cargo shorts are bad, but ones inspired by outdoor gear and military designs are great. Pair them with hardcore tees, chambray shirts, and flannels. Even Kermit co-signs.
Turtlenecks
Layer a wool turtleneck under flannel suits, corduroy or tweed sport coats, or winter outerwear. Thin ones have English professor vibes; chunky ones have Maine Guy vibes. I think the second is easier to style, but it can get very warm indoors.
Pro Sports Jerseys With Another Man's Name on the Back
This is one of the best fits of all time. What do you mean??
Jewelry
Native American jewelry looks great with casual tailoring and workwear. Brands such as Werkstatt Munchen work with brutalist avant-garde. Even Cary Grant wore a thin gold chain with pendants in the ne plus ultra of classic menswear films, North by Northwest.
Baseball Caps
Maybe not with a formal business suit, but fine with casualwear. I've even seen some guys look great wearing a baseball cap with casual tailoring.
Pleated or Cuffed Pants
Both serve a purpose. Pleats give you more room at the thigh and they visually break up the expanse of fabric that can take up your lap. Cuffs help tailored pants hang better. Also looks great on jeans. Again, it's all about knowing how to style things.
Sneakers with Suits
Sneakers look bad with formal suits because there's a big gap in formality (pic 1). But not all suits are formal! You can wear simple white sneakers with cotton, linen, or seersucker suits (pics 2, 3). Or with sport coats, which are less formal still (pic 4)
Hoodies look great with workwear. Think chore coats, trucker jackets, or bombers paired with Dickies, jeans, or carpenter/ painter pants. I like them best in the rugged, stout variety that takes after mid-century originals.
Double-Breasted Suits
There's nothing hard about wearing a DB suit; it's just challenging to find one that fits. There aren't that many in RTW, which limits your options. Many also have high buttoning points, which look worse in a double-breasted than a single-breasted.
However, if you've found one that fits, you can wear it just like a single-breasted suit. Pair it with a dress shirt or a more casual top (e.g., turtlenecks, long-sleeve polos, or even the right T-shirt). If you wear it open, sweep the flappy front to your side with your hand
Skinny jeans look great when they're in an outfit that has a rock-and-roll vibe. They look awful when they're in business casual outfits with tiny sport coats and duck-feet orange dress shoes (pic 4).
Again, it's all about knowing how to style things. @modsiwW has a few great videos on this. Oftentimes, the guy just needs the right pair of boots and something like a leather jacket.
@modsiwW
In defense of skinny jeans….again. https://t.co/1ypzpbo5hI
Oxford is a type of fabric commonly used to make button-down collar shirts. So I'm not sure if the OP meant to write "button-down collars." If so, any American against BD collars should be deported for not knowing this country's history. Even Italians like them.
Backpacks
Backpacks look great with casualwear. I especially like ones inspired by 1970s hiking gear, which can be worn with similarly styled clothes. Don't use backpacks with suits or sport coats, though, because you can ruin the shoulder line.
Bowties Without A Tuxedo
Bowties certainly aren't for everyone, but not everything has to be. They look great with American sack coats, button-down shirts, and alpca cardigans. Also great for eveningwear, such as velvet jackets.
Monkstraps and Tassel Loafers
Two of the most elegant footwear options for men who wear tailoring. I think black calfskin tassel loafers are especially useful, as they can be worn in any situation where you can imagine wearing a black knit tie (so most tailored outfits)
Baggy Clothes
I've written a ton on here about how clothes often look better when they have "shape and drape." That means clothes with a silhouette that's different from just your corporal form. One only needs to look at a Lemaire runway show to appreciate this concept.
But even if your taste runs more conservative, some clothes straight up look worse when they've been slimmed up: duffle coats, trench coats, and Balmacaans among them. Even the Harry Met Sally Aran that went viral last year was largely about a difference in fit.
Graphic T-Shirts
Graphic tees look great with casualwear. Depending on the pieces, the right graphic tee can even worn with tailoring! I prefer vintage graphic tees, but new ones worn long enough eventually become vintage anyway.
Women's Clothing
I don't know how anyone can be so declarative about this statement when Prince and David Bowie were among the most stylish men of the 20th century. Or look at the New York Dolls, Kanye's Pheobe Phio moment, or modern icons like Billy Porter.
Ultimately, these sorts of statements come from a place of fear and prejudice: fear of standing out or being perceived as gay or feminine. As a result, many then end up wearing the blandest possible uniform and maybe a watch that they hope impresses people.
That list is nothing more than barbed wire to fence you into class-based norms about respectability. However, true respectability comes from your character, and it takes more than clothes to be perceived as upper-class. So who cares about such charades? Have fun with clothes.
