How to Dress Rich - Old Money

Back in March, the Husband and I enjoyed an amazing night at the Bristol. It was a gift from my parents and probably the most amazing thing about that night was that we got a complimentary upgrade. We laughed, we danced and then I stopped and said in a serious tone to the Husband "It's cause we dressed rich an you know it." And then I danced some more and drank Moet Chandon straight from the bottle. I have class and you know it.

Dressing rich is not that hard and doesn't have to cost that much. Now I am not talking about Kardashian rich (that money is the money of Satan), I am talking old school money, country clubs and drinking scotch. Here are some tips to how you can dress to look rich for different occasions (please note that this is in no way making fun of rich people, poor people or any people. This is based on observations on my part and the deep seated desperation of wanting to be a rich WASP from the East Coast. Pick me!). Dressing old school money pretty much means dressing preppy. Come join me for this wonderful trip of tweed and cotton and forced laughs.

Casual wear:
Rich people enjoy casual wear. And by casual wear, I don't mean track suits with the word "JUICY" stretched across the derriere. Mon dieu! The typical uniform is tailored jeans, crisp button up shirt and a blazer. Colour combos can vary:

Red jeans
Blue and white striped shirt
Navy blazer (preferably with Ralph Lauren emblem)

Blue jeans
White shirt
Red blazer

Blue jeans
White shirt
Tweed blazer with arm patches

And so on...

Footwear? Tory Burch loafers or ballerinas, in the fall, brown leather boots Purse? Large, structured, handles. Leather. Jewelry? Tasteful and small. Gold studs, small chain bracelet, thin chain necklace, large heritage engagement ring. Hair? Any colour but no crazy streaks. Held back by aviator or tortoise shell sunglasses. A little chilly out? Pashmina in a neutral colour: caramel, navy, red, folded in half and ends pulled through or around your shoulders. Or wear a cravat. Below is an example (without that belt, too gaudy. I love it, though). Get a belt in a warm brown with a simple buckle.

What you should invest in: In order to not, you know, become poor when trying to dress rich, aim to avoid too many brands. Shirts can be purchased at normal stores - just make sure they are always crisp, clean and well fitted. Same for blazers. Gold jewelry can be fake jewelry. A "silk" scarf in a classic print can be purchased cheaply and when it is folded and tied up, nobody can tell it isn't an Hermes. You can get great faux leather purses. Make sure they are clean. Caramel/brown coloured ones are great and neutral and match a lot of things. For foot wear, plain ballerinas can be bought on the cheap and no one will no if they are brand name or not. Jeans don't have to be brand name but have to look new. No scruffy hems or rips. And not too flared, if at all.

Now I said casual wear, but by casual I mean weekend: shopping, lunch with friends, sitting on your boat as it's docked. There's casual wear and then there's casual wear. Sport afternoon at the kid's school? Gardening? Wear a polo.

What you should invest in: A couple of real Polo shirts. They are pricey but they last a long time. Jeans, see above. Footwear pretty much the same. But if it is muddy and raining on the grand estate you are visiting, wear Hunter boots. Cardigans with elbow patches are good too. Jodhpurs are amazing but if you don't own a horse, try and skip them.

An evening out:
Rich people be inviting you to a dinner? What to wear? Keep it simple. There is a reason the little black dress continues to be a staple in every woman's wardrobe. Pair it with pearls, transparent stockings and a mid heel in black. Keep it simple. Here are some examples below. No cleavage and nothing too short.

If it is an event during the day, purchase a few sheath dresses in different colours. Heels can be a variety of coulours but nothing too flashy. Pair with a cardigan. Wear your hair in a simple chignon or give yourself a blowout. Simple with no accessories showing; i.e. scrunchie or hair claw.

What you should invest in: A little black dress and some simple coloured sheath dresses. Simple fake pearls. Practical but attractive pumps.

Saving money tip to look rich: buy a generic cardigan, remove plastic buttons and add fake gold ones. It makes all the difference.

The real key to dressing old money rich is to keep it clean, simple and classic. Nothing flashy. The clothes should look tailored so even if you buy cheap, make sure it fits you impeccably. A quick trip to the tailor can work wonders.

Do I dress this way? Nope, only to get upgrades or good seats at a restaurant. Remember, this is just a fun post and not the only way to dress. Embrace your own personal style because, in my opinion, that is what fashion is really about. Home, James!