An Old Money Year-Round Capsule Wardrobe: How To Dress Old Money All Year Long

Some of the links below are affiliate links, meaning that at no additional cost to you, I will receive a commission if you click through and make a purchase.

Sometimes, finding the right garments for each season can be overwhelming. For that reason, and to avoid spending money on the wrong garments, you need a year-long capsule wardrobe with practical items that fit you beautifully and, on top of that, make you look rich and elegant.

If you want to dress in old money, we have a complete, extremely simple guide with useful tips on how to do so and a year-round capsule wardrobe with outfit ideas for you.

A complete guide on how to dress old money all year long

Dressing old money in summer

White dress – Black dress – Striped shirt – Black top – Scarf – Shorts – Brown pants – Cream pants – Pearl necklace – earrings – hat – sunglasses – watch – belt – handbag – ballet flats – mules

To dress old money in summer, you need to fall in love with linen garments, suit pants, dressy flats such as loafers, and button-downs.

When it comes to accessories, rectangle or oval sunglasses are a must, as well as a silk scarf, a high-end bag, and a sun hat.

Regarding jewelry, old money women wear a few jewelry pieces that scream class and expensive. Such pieces include a pearl necklace, a vintage watch (preferably small), a thin bracelet, and a plain gold ring.

Key style tips to nail this style in summer

Avoid oversized garments at all costs.
All pants and shorts should be high-waisted.
Always go for a natural makeup look since it looks more polished and sophisticated.
Tops and blouses must be tailored.
Midi dresses are always the best option. They can even look more elegant than long ones.
Dressy shoes such as ballerina flats, loafers and mules are key to looking old money rich all year long.
Queen Anne, Collar, and Boatneck are the most refined necklines to wear in summer.

Dressing old money in spring

White polo – Striped top – Black top – Linen blazer – Skirt – Pants – Striped dress – Black dress – Loafers – Beige heels – White Heels – Sunglasses – Earrings – Heeled sandals

For tops and blouses

Thin, long-sleeved sweaters, a button-down layered with a sweater vest, a sleeveless turtleneck, or a striped blouse are the best choices if you want to look old money in spring.

For pants and skirts

The best options are Midi skirts (preferably pleated), cropped pants, and white jeans.

Important note: If you want to dress old money, make sure all your pants and skirts are neutral-colored. They’re easier to style and dress up and will make you look slimmer.

For shoes

Slingback heels and loafers are the most old money style shoes you can wear in spring. However, ballerina flats can be a more comfortable, equally elegant choice.

For accessories

The top spring accessories are a scarf (cotton for those colder days and silk for the hot ones), a headband, a brown belt, and a timeless bag.

You can opt for a gold bracelet and a statement necklace for jewelry.

Key style tips for dressing old money in spring

Make great use of classic accessories to elevate the look.
If you’re wearing a dress, make sure it fits like a glove. If not, add a belt to add definition.
Tie a silk scarf to your handbag.
Fall in love with kitten heels.

Dressing old money in the fall

Navy Blazer – Brown blazer – Button-down shirt – Sweater vest – Skirt – Dress – Pants – Trench coat – Loafers – Ballet flats – Heels – Belt – Handbag – Boots

Dressing old money in fall and winter might require some extra work since you need to add more layers and pay more attention to detail.

For tops and blouses

Turtlenecks and polo sweaters are a must, as well as tailored blazers and a trench coat.

If you don’t like polo sweaters, you can opt for a classic v-neck (preferably white or beige) or a long sleeve with a square neckline.

Regarding dresses, long-sleeved dresses or a shirt dress layered with a blazer are the top choices.

Fashion tip: Sweater vests will make you look effortlessly classy and expensive, so make sure to add at least a neutral-colored one to your fall and winter wardrobe.

For pants and skirts

Opt for long, wide-leg pants and tailored midi skirts to pair with heeled boots.

For shoes

Heeled boots, especially knee-high boots, are a must-have for looking old money, as well as classic pumps.

For jewelry and accessories

Elegant earrings (preferably pearls) and a watch are the only and most sophisticated pieces you should wear in fall and winter. With all the layers, it is not necessary or elegant to wear anything more than that.

However, if you want to wear a necklace, make sure it’s thin.

Additionally, cotton scarves and a classic black handbag are timeless wardrobe essentials for cold days.

Tips on how to dress old money in the fall

Always tuck in your shirts, especially if you’re wearing layers.
Don’t wear too much jewelry when wearing two or more layers. It can cheapen the look.
Opt for heeled shoes to look more sophisticated
Avoid cropped and oversized blazers

Dressing old money in winter

White coat – Brown coat – White turtleneck – Black turtleneck – White pants – Dress – Scarf – Gloves – Loafers – Heels – Handbag – Watch – Belt – Boots

For tops and blouses

Long-sleeved turtlenecks and sweaters with elegant necklines such as Square, collar, Queen Anne and scoop are the most practical and old money aesthetic choices.

For pants and shoes

Just like in fall, straight suit pants (preferably wide-leg) and tailored midi skirts are the most expensive-looking choices, as well as knee-high boots.

For coats

A tailored and well-structured white or cream coat is a must if you want to look old money rich. You can also opt for a timeless long black or dark brown coat; it’s more versatile but maybe not as chic.

Remember, for a coat to look more elegant and expensive, it should have shoulder pads and buttons of the same color. Shoulder pads help the coat look more structured, while seamless buttons keep it classy.

For accessories

Gloves are a must for both practical and fashion reasons. They’re key to elevating any winter outfit.

A Minimalist bag is a must in winter to avoid an overwhelming look and keep it elegant and stylish.

Tips to look old money in winter

Stay away from oversized coats.
Never leave home without grooming and styling your hair.
Wear a perfume that smells expensive.
Fall in love with heeled boots.
Keep nails simple and wear neutral colors that go well with any outfit and accessory.

You might also love