Old Money Outfits

The old money vibe is a fashion trend that gets inspiration from the richest families of the past, mixing old-school preppy fashion with modern silhouettes. It’s all about high quality, timeless pieces, rich fabrics, neutrals, lowkey elegance, minimalist designer items, and an overall understated vibe. What makes it so cool is that it’s effortlessly sophisticated and timeless. You get classic outfits that also feel modern, with quality over quantity. It’s not about showing off wealth, but more about subtle luxury and understated style. In this post, I’m excited to share some old money outfit ideas that you can easily recreate. They’re versatile, timeless, and perfect for any occasion, whether you need inspo for brunch or the office. So, if you’re looking to add some old money style to your wardrobe, keep reading for some inspiration.

Also, for more classic and timeless essential wardrobe pieces, check out my Fall Capsule Wardrobe here.

Old Money Outfits

Sharing a variety of old money outfit ideas from casual chic daily attire to more elevated dressy looks. There is something for everyone and every occasion.

Sweater Dress + Leather Jacket Outfit

Embrace the classic old money look this fall with a simple yet elegant sweater dress outfit. A cozy sweater dress paired with brown leather boots is a chic and timeless look. Top it off with a brown leather jacket and matching accessories to complete the outfit. This combination of classic textures and layers is perfect for an old money autumn outfit idea.

Plaid Coat + Jeans Outfit

One of my favorite ways to achieve a chic old money look for fall is by pairing classic jeans with a plaid coat. Regardless of the style, a plaid coat remains a timeless piece that effortlessly adds sophistication. Complete the look with ankle boots and a few accessories, and you’re all set for a stylish autumn outfit idea.

Black Skirt Outfits

A black skirt is an old money staple in every wardrobe, versatile enough to transition seamlessly from summer to fall. For an elevated casual look, pair it with a simple white t-shirt and sneakers for an effortlessly chic outfit. Or, when dressing for a more formal setting, like work, switch to a cozy sweater and elegant heels outfit. This classic skirt can adapt to both dressy and casual styles, making it a timeless piece for any occasion.

White Jeans Outfit

You don’t have to stop wearing white outfits after summer. In fact, white jeans are a classic old money staple, perfect for fall and winter. Dress them up with boots and elegant accessories for a chic outfit idea, or go casual with sneakers and a simple jacket. White jeans are definitely a great piece to have in any cold weather old money wardrobe.

Striped Sweater + Black Pants Outfit

A striped sweater is a popular, yet timeless item for achieving an old money look in colder weather. It pairs beautifully with black pants and either boots or loafers, perfect for various occasions. Whether you’re heading to work or just out to explore the city and run errands, this outfit provides a chic and polished look that’s effortlessly stylish.

Grey Jeans Outfit

Grey jeans are a stylish twist on traditional blue jeans and perfect for an old money look in fall. Pair them with a blouse and blazer for a chic business casual outfit. You can also wear them with boots for a polished look or sneakers for a more relaxed feel, making them a versatile addition to your wardrobe.

Blazer + Relaxed Denim Outfit

A blazer and relaxed denim jeans outfit perfectly embodies the old money aesthetic because its effortlessly cool and timeless. It strikes the balance between casual and elevated, making it a go to for any occasion. To achieve this look, investing in good quality pieces is key, particularly in neutral colors like a tan blazer and matching accessories, for a sophisticated and understated vibe.

Old Money Outfits
Old Money Outfits

Linen Blazer | White Heeled Sandal | 90s Jeans | Linen Top | Double Breasted Blazer | Half-Zip Sweatshirt

Monochrome White Outfit

An all white monochrome outfit is always a classy option that fits perfectly into the old money sophisticated look. This minimalist approach exudes a chic and timeless vibe that works well for both workwear and special occasions. To elevate the look, pair a white blazer with matching trousers. Then, add a pair of heels and a coordinating handbag for the perfect finishing touch.

Monochrome White Outfit

Shop The Outfit

Casual Chic Outfit

Old money aesthetic is not limited to formal wear and even daily casual outfits can achieve the same vibe. The key is to choose well fitting, good quality pieces in neutral or understated tones. For instance, pairing a navy casual sweater with high quality denim jeans, classic white sneakers, and a white handbag can create a chic and effortless outfit that exudes understated elegance.

Casual Chic Old Money Outfits

White Oxford Sneakers | High Rise Jeans | Sweatshirt

Tan Coat Outfits

The old money aesthetic is not only about choosing the right pieces but also the right colors. Tan and white are a great combination that are always sophisticated. For a chic and classy look, try pairing a tan long coat over your white pants outfit. Whether it’s a classic long pea coat or a trench coat, the length of the coat will elevate your outfit and keep you warm during colder months.

Tan Coat Old Money Outfits
Tan Coat Outfits

Outfit 1 | Outfit 2

Elevated Casual Shorts Set Outfit

Creating an old money aesthetic outfit doesn’t have to be limited to formal wear, as you can still look classy in a elevated casual outfit. A white casual shorts set paired with classic accessories, such as a neutral sweater and tote, can quickly achieve the look you want. Not only is it easy to style and put on, but it’s also perfect for running errands or picking up the kids while looking effortlessly chic.

Elevated Casual Shorts Set Outfit

Naghedi Tote Bag | Half-Zip Sweater | White Shorts

White Linen Dress Outfit

The white linen dress is a staple of old money aesthetic for spring and summer. The shift dress shape and all white linen fabric are perfect for creating an elevated summer look. Complete the look with chic accessories such as gold jewelry, sandals, and a woven tote bag.

White Linen Dress Outfit

White Linen Shift Dress

Monochrome Black Shorts Outfit

A monochrome black outfit is a classic and timeless old money outfit idea that is flattering on everyone and easy to style. For summer or spring, pairing black shorts with heels, a black leather jacket, and matching accessories can create an effortlessly chic and elevated look. Wear this outfit to the office, exploring the city, or getting lunch with friends.

Monochrome Black Shorts Outfit

Black and White Skirt Outfit

The black and white color combination is a timeless classic that never goes out of style and is perfect for achieving an old money aesthetic outfit. Styling an outfit with these colors is an easy and versatile option whether you need a dressy or a more casual look. For example, a black and white skirt outfit, whether long with a button down blouse for a workwear look or shorter with a lace blouse for a daytime look, can be versatile and perfect for different occasions.

Black and White Skirt Old Money Outfits
Black and White Skirt Outfit Ideas

Satin Slipdress | White Button Up | Slingback Pump | Mini Colette Bag

Monochrome Knit Skirt Outfit Idea

A monochrome cream knit skirt outfit is a great option for achieving an old money aesthetic outfit in spring and summer. Monochrome outfits in any neutral colors are an easy way to style a classy look. The long skirt provides modesty while still being modern and on trend, making it a perfect choice for achieving that old money aesthetic this summer.

Monochrome Knit Skirt Outfit Idea

Ribbed Sweater Tank | Knit Midi Skirt

Button Down + Denim Outfit Idea

Pairing classic denim jeans with a button down shirt is an all time classic outfit idea that will surely never go out of style. This combination can instantly elevate any look and is perfect for any casual chic occasion. Adding a belt and a chic handbag can accentuate the waist and complete the effortlessly sophisticated look.

Button Down and Denim Old Money Outfits

Button Down Shirt | High Rise Jeans | Flats

Black and White Lace Dress Outfit Idea

A lace dress is another great option for styling the old money aesthetic as it is a timeless and feminine fabric that exudes class. You can style lace in many ways to achieve different looks, whether it’s a classic dress or a blouse. For an old money look, try pairing a white lace dress with black heeled booties and a matching bag for a feminine and sophisticated outfit.

Lace Dress Outfit Idea

Slip Skirt + Sweater Neutral Outfit Idea

Using different textures in an outfit can add depth and interest, but for an old money aesthetic, stick to neutral colors and quality pieces. Try pairing a lace slip skirt with a chunky knit sweater in a neutral shade. Finish the look with brown heels and a matching shoulder bag for a classic look perfect for exploring the city, grabbing lunch with friends, and more.

Slip Skirt and sweater outfit

Slip Dress

Grey Denim Trench Coat Outfit Idea

Sticking within the same color palette is a great way to create an old money aesthetic look. Choosing different shades of one color can make your look appear more cohesive and put together. For a chic yet edgy outfit idea, try pairing cool toned gray denim with a matching lavender trench coat, and finish the look with a pair of classic heels.

Grey Denim Trench Coat Outfit Idea

Leather Jacket + Denim Outfit Idea

A black leather jacket and denim jeans outfit is a classic and timeless old money aesthetic look. It’s effortlessly cool and sophisticated, and can be dressed up or down. For a chic date night look, add black heels and a matching black handbag.

Leather Jacket and Denim Old Money Outfits

How To Look Old Money

Invest in high quality, timeless pieces:

Stick to classic and well made clothing that never goes out of style. Neutral colors such as black, white, cream, navy, and beige work well.

Accessorize with classic pieces:

Go for understated and timeless accessories such as pearl earrings, a leather tote bag, a gold watch, or a silk scarf. They add elegance and sophistication to any outfit. And, if you are love designer handbags, check out my favorite here. For designer inspired handbags on a budget check out my post here.

Embrace simple and clean lines:

Be sure to avoid anything too flashy or trendy. Old money fashion includes simple and clean lines with a focus on fit, quality, and style.

Wear the right shoes:

Footwear plays an important role in creating an old money aesthetic look. Go for classic styles such as loafers, pumps, or simple sandals. Avoid anything too trendy.

Pay attention to grooming:

Looking old money isn’t just about the clothes you wear, it’s also about your grooming. Keep your hair well maintained, wear minimal makeup, and make sure your nails are clean and polished. Attention to detail is key to achieving an old money aesthetic look.

Invest in high quality fabrics:

Such as cashmere, silk, and linen to ensure that your clothes look and feel luxurious, even if they are simple and understated.

Invest in high quality pieces:

While not everything you own needs to be designer, or expensive. Make sure that you take the time to invest in high quality pieces that will last you a lifetime, rather than spending money on trends.

Some old money aesthetic places to shop are:

Ralph Lauren, Mango, Reformation, Stuart Weitzman, Saks Fifth Avenue, Bloomingdales, Net-A-Porter, Neiman Marcus, Nordstrom, and more.

Please feel free to email me at thegraydetails@gmail.com if you have any questions!  I’m always happy to help with styling or picking out a specific outfit for an event!   Have an amazing day!!

Also, check out my instagram shop HERE to shop all my instagram looks, style guides, gift guides and fashion tips.

You can also download the free LIKETOKNOW.IT app and follow me HERE.

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As always, thank you so much for stopping by today, I truly appreciate all of you! xx, Amanda


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  1. 7.20.23
    Joy Laufle said:

    In your spring capsule collection, there are a pair of high waisted, flared leg white jeans. However, I could not find a link for those anywhere.


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