How do wealthy men dress on the weekends?

[Anonymous]

You're at a coffee shop on Saturday morning. A 35 to 45 year old man walks in with a young child and based on his appearance, you assume he's wealthy. What's he wearing that gives you that impression?

[Anonymous]

It's impossible to tell. I have a friend from college whose husband founded a company that netted the founders tens of millions a piece when it was bought out. He wears champion sweat pants and a faded college hoodie when he isn't working

[Anonymous]

It's not just about his clothing. Hair and facial grooming tells me a lot. What his nails look like. Also glasses, if he wears glasses. Shoes say a lot too. So curious though why you're asking such a specific question "35-45yrs...young child..." hmmm....

[Anonymous]

I think there’s a certain preppy confidence- sometimes accompanied by boat shoes and a polo- that gives wealthy Republican vibes.

But I agree that you can’t really know. I’ve known some very shlubby but very wealthy people who just wear whatever they want.

[Anonymous]

The standard is jeans (dark denim, fitted by not tight from JCrew, Levis, or maybe a slightly pricier brand, but these guys don't spend as much on denim or buy as showy denim as their wives) or khakis (Bonobos, JCrew, or similar), a pair of sneakers from All Birds or ON, or maybe Adidas or Onitsuka Tiger depending on how their personal style leans (yes, this is the level of differentiation in personal style in this set, it is very subtle). And a black or other dark neutral fleece jacket. Jacket will either be plain Patagonia, Arcteryx, North Face, or potentially a branded jacket from work (AmLaw 50 firm, consulting or finance firm).

Under the jacket will be a nice t-shirt from Everlane or maybe a lightweight sweater from Everlane, Brooks Brothers, or similar price point. If they are coming from church, they might swap the t-shirt out for a collared shirt, but definitely no tie.

In the summer, they might wear a short sleeve collared shirt from JCrew, Brooks, or a brand like Grayers. May trade out the jeans for khaki shorts, not too short but cut somewhat slim. Will usually still stick with sneakers but an intrepid minority might wear a pair of Birkenstocks. Only if feet are well tended.

Haircut will be fresh (these guys get it trimmed once a month at a minimum, I know men who do it weekly), fresh shave or neat beard trim. Neat nails. No jewelry except wedding ring, no visible tattoos.

[Anonymous]

Anonymous wrote:I think there’s a certain preppy confidence- sometimes accompanied by boat shoes and a polo- that gives wealthy Republican vibes.

But I agree that you can’t really know. I’ve known some very shlubby but very wealthy people who just wear whatever they want.

1990 called and they want their preppy stereotype back.

It’s less about clothes and more about how their grooming. Are they fit? What about hair and nails? Also look at their shoes. Wealthy people tend to spend more on shoes. At a coffee shop I’d expect the mythical man you’re looking to describe to be wearing either well-fitting jeans or lululemon (or similar brand) pants like ABC. A well fit solid t shit or v neck and now that it’s cold maybe a solid colored pull over (no branding). Also maybe a baseball hat but it has to be from their alma mater if they went Ivy or solid (definitely no sports teams).

[Anonymous]

i ran into a very successful friend the other day in the grocery store, his sneakers were probably 10 years old, wearing sweatpants that looked like they were from his freshmen year in college, and a t shirt that looked like he found it in the street.

[Anonymous]

Anonymous wrote:

Anonymous wrote:I think there’s a certain preppy confidence- sometimes accompanied by boat shoes and a polo- that gives wealthy Republican vibes.

But I agree that you can’t really know. I’ve known some very shlubby but very wealthy people who just wear whatever they want.

1990 called and they want their preppy stereotype back.

It’s less about clothes and more about how their grooming. Are they fit? What about hair and nails? Also look at their shoes. Wealthy people tend to spend more on shoes. At a coffee shop I’d expect the mythical man you’re looking to describe to be wearing either well-fitting jeans or lululemon (or similar brand) pants like ABC. A well fit solid t shit or v neck and now that it’s cold maybe a solid colored pull over (no branding). Also maybe a baseball hat but it has to be from their alma mater if they went Ivy or solid (definitely no sports teams).

Do Mt Gay regatta hats qualify as a sports team?

[Anonymous]

Mine wears Kirkland jeans and sneakers. Nice leather jacket but that’s because I bought it for him.

[Anonymous]

Mine wears wrangler jeans or Eddie Bauer pants college baseball hat and some sort of company logo top and either Nikes old ones like super old or boots (extremely expensive over $2000)

No one would ever think my dh has money lol

Then again Steve Jobs only wore jeans and turtlenecks

[Anonymous]

Spats, tails, top hat. Think the Monopoly man.

[Anonymous]

Could be wearing anything, impossible to tell. Most likely jeans/sweatpants and a T-shirt or fleece... just like everyone else.

[Anonymous]

The quarter zip: https://www.theguardian.com/fashion/2023/mar/04/quarter-zipper-becomes-the-new-status-symbol-for-men-of-a-certain-position

[Anonymous]

They wear t-shirts with the phrase "Get Lost Gold Digger" on the front (to you).

[Anonymous]

This is hilarious. I can't think of much that I would see on a man in a coffee shop that would make me think he's wealthy. Nice watch? Nice belt? Clothes that are clean, fit well, and appear to either be new or to have been professionally laundered or dry cleaned? Nice fabrics (he's in the same style sweater as everyone else but his is cashmere)? In your hypo, I'd look at the kid and she how he or she is dressed. If the kid is in fancy labels to bomb around with dad on the weekend the family is probably doing pretty well.