Old money style is synonymous with a level of sophistication and class that transcends trends. It embodies an understated elegance that focuses on quality over quantity, making it ideal for anyone seeking to elevate their fashion game with timeless pieces. In this blog post, we’ll explore 17 essential outfits that perfectly embody the old money dress aesthetic, ensuring you look effortlessly stylish while remaining true to the understated luxury associated with the old money style.
Whether you’re dressing for a formal occasion, a business meeting, or a casual weekend gathering, the following outfit ideas will help you create a wardrobe that reflects elegance and sophistication. These looks combine traditional fabrics, tailored fits, and luxurious accessories—key elements of classic fashion.
Classic Tweed Suit: The Foundation of Old Money Dress
The tweed suit is a hallmark of old money fashion. Known for its timeless charm, tweed suits are not only stylish but incredibly durable, making them perfect for almost any occasion.
- Why Tweed? Tweed has been a staple in classic fashion for centuries. This rugged yet refined fabric is known for its warmth and versatility, making it ideal for cooler seasons.
- How to Style It: Pair your tweed suit with a simple white shirt, a silk tie, and leather dress shoes for a polished, sophisticated look. Add a pocket square for extra flair.
- Pro Tip: To keep your look modern and chic, opt for a slim-cut tweed suit. Avoid overly bold patterns or bright colors, sticking to muted tones like grey, navy, or deep green.
Perfect For: Formal gatherings, business meetings, and upscale events.
Tailored Blazer and Chinos: Business Casual Excellence
A tailored blazer paired with chinos is the perfect embodiment of the old money dress code for business casual attire. This combo blends comfort with refinement.
- Key Elements: A well-tailored blazer ensures that you look polished, while chinos keep the look comfortable and breathable.
- Color Pairing: Go for neutral shades like navy, charcoal, or beige. A tweed blazer can also be an excellent option to add some texture.
- Pro Tip: Always ensure that the blazer fits perfectly at the shoulders, as this is a tell-tale sign of good tailoring. A slightly tapered chino will also elevate the overall aesthetic.
Perfect For: Smart-casual office days, business lunches, or evening drinks.
Tuxedo with White Tie: Formal Perfection
The tuxedo with white tie is the epitome of formal attire in old money fashion. It’s a rare and ultra-refined look that signifies the height of elegance.
- White Tie Details: A white tie event typically calls for a black tuxedo with a white pique cotton shirt, a white bow tie, and black patent leather shoes.
- Accessories: Complement the tuxedo with cufflinks and a waistcoat. Consider a silk pocket square for the finishing touch.
- Pro Tip: Ensure the tuxedo is perfectly tailored to your body to achieve that ideal timeless aesthetic.
Perfect For: Galas, high-end charity events, and formal balls.
Cashmere Dress
A Cashmere Dress exudes both luxury and warmth, offering an effortlessly chic and comfortable look. Cashmere is known for its softness and warmth, making it a perfect choice for cooler months. Whether you opt for a fitted sheath or a flowy A-line, the understated elegance of a cashmere dress aligns perfectly with old money style. Pair it with leather accessories or simple jewelry to create a polished, luxurious outfit.
| Idea | Details |
|---|---|
| Best For | Casual chic outings, evening events, cocktail parties |
| Fabric | Cashmere |
| Key Accessories | Leather clutch, silk scarf, simple gold jewelry |
| Ideal Footwear | Ballet flats, dressy ankle boots, loafers |
| Season | Fall, winter, early spring |
Linen Sheath Dress
A Linen Sheath Dress offers effortless elegance and is perfect for warmer weather. The lightweight, breathable fabric makes it ideal for spring and summer outings while still looking polished. This old money dress is perfect for semi-formal events like garden parties, luncheons, or casual day events. The clean lines and minimalist design make it an excellent choice for creating a sophisticated, yet relaxed look.
| Idea | Details |
|---|---|
| Best For | Summer luncheons, garden parties, semi-formal day events |
| Fabric | Linen |
| Key Accessories | Simple gold jewelry, wide-brimmed hat, sunglasses |
| Ideal Footwear | Wedges, espadrilles, sandals |
| Season | Spring and summer |
Flannel Shift Dress
A Flannel Shift Dress provides a cozy, refined look perfect for fall and winter. The soft, tactile feel of flannel combined with the timeless shape of a shift dress creates a comfortable yet sophisticated appearance. This dress can be dressed up with a velvet blazer or worn casually with equestrian boots for a classic old money style vibe.
| Idea | Details |
|---|---|
| Best For | Fall and winter gatherings, casual daywear, weekend brunch |
| Fabric | Flannel |
| Key Accessories | Leather gloves, brooches, wool beret |
| Ideal Footwear | Tall boots, ankle boots, loafers |
| Season | Fall and winter |
Velvet Evening Dress
The Velvet Evening Dress is an elegant, opulent piece perfect for formal evening events. Velvet, with its rich texture and sheen, offers a regal, luxurious feel that aligns seamlessly with old money style. Whether in deep jewel tones or muted earth hues, a velvet evening dress paired with diamond jewelry or a sleek clutch will ensure you exude sophistication at any black-tie affair.
| Idea | Details |
|---|---|
| Best For | Black-tie events, gala dinners, formal parties |
| Fabric | Velvet |
| Key Accessories | Diamond earrings, sleek clutch, silk shawl |
| Ideal Footwear | High heels, satin pumps, open-toed shoes |
| Season | Fall, winter, holiday season |
Silk Wrap Dress
A Silk Wrap Dress is the ultimate in refined luxury, offering elegance and comfort with its smooth, flowing fabric. The wrap silhouette flatters many body types and is especially perfect for evening wear or more relaxed events like a dinner party. The fluidity of silk adds a touch of romance, making it a quintessential old money dress for those looking to exude class with every step.
| Idea | Details |
|---|---|
| Best For | Dinner parties, evening events, cocktail parties |
| Fabric | Silk |
| Key Accessories | Diamond bracelet, pearl clutch, statement earrings |
| Ideal Footwear | Satin pumps, pointed-toe heels, strappy sandals |
| Season | Year-round, though best for warmer months |
Leather Jacket and Chinos: A Chic Twist on Casual
A leather jacket paired with chinos offers a more rugged yet still polished look. While leather jackets can sometimes come off as edgy, when styled correctly, they can fit seamlessly into old money style.
- Leather Jacket Selection: Go for a classic, simple design with clean lines. Avoid overly distressed leather or flashy embellishments.
- Pairing: Combine the jacket with chinos for a smart-casual aesthetic. Opt for neutral-colored chinos like beige or navy.
- Pro Tip: Leather should never look overused or cheap. Invest in a high-quality leather jacket that has a tailored fit for a sophisticated silhouette.
Perfect For: Casual evenings, weekend outings, and informal business functions.
Corduroy Blazer & Trousers
When styled correctly, a corduroy blazer with trousers can be a fantastic choice for a polished, relaxed outfit.
- Material Perks: Corduroy offers a comfortable, textured fabric that pairs well with the more formal, tailored nature of chinos or wool trousers.
- Styling Tips: Stick to earthy tones like olive, tan, and brown for the ultimate elegant fashion look.
- Pro Tip: A corduroy blazer should be fitted at the waist, and trousers should have a slight break to ensure a refined silhouette.
Perfect For: Fall outings, business meetings, or casual family events.
A-Line Wool Dress
An A-Line Wool Dress is a timeless and flattering silhouette that combines comfort with class. The wool fabric makes it ideal for colder weather, offering warmth without sacrificing style. This classic dress can be worn to both business events and casual gatherings, with its structured yet feminine shape providing a sophisticated appearance. Pair it with a long wool coat or a silk scarf to achieve that old money style.
| Idea | Details |
|---|---|
| Best For | Business events, formal lunches, holiday parties |
| Fabric | Wool |
| Key Accessories | Leather gloves, silk scarf, pearl necklace |
| Ideal Footwear | Knee-high boots, heeled loafers, ballet flats |
| Season | Fall and winter |
Tailored Cashmere Midi Dress
A Tailored Cashmere Midi Dress brings a perfect blend of elegance and comfort. Cashmere’s luxurious softness and warmth are the highlight of this piece, while the tailored cut ensures it offers a sophisticated fit. This dress works perfectly for those who want a chic yet cozy look for both formal and semi-formal events. Pair it with classic leather handbags and diamond studs for an elevated look.
| Idea | Details |
|---|---|
| Best For | Evening events, formal dinners, winter galas |
| Fabric | Cashmere |
| Key Accessories | Diamond studs, leather handbag, simple bracelet |
| Ideal Footwear | Pumps, pointed-toe heels, classic loafers |
| Season | Fall and winter |
Long Sleeve Silk Dress
A Long Sleeve Silk Dress combines luxury and elegance with its soft, flowing texture. The silk fabric drapes beautifully, and the long sleeves make it a perfect option for those who want to keep a sophisticated and modest appearance. Ideal for evening occasions, this dress enhances old money style with its rich simplicity. A cashmere shawl and elegant heels can elevate this dress to the next level.
| Idea | Details |
|---|---|
| Best For | Evening parties, upscale dinners, formal events |
| Fabric | Silk |
| Key Accessories | Cashmere shawl, simple diamond earrings, delicate watch |
| Ideal Footwear | Heeled sandals, satin pumps |
| Season | Year-round, but ideal for fall and winter |
Shirt Dress in Cotton
The Shirt Dress in Cotton is a versatile and comfortable choice that retains an air of sophistication. The cotton fabric offers breathability, making it perfect for warm months while still keeping you looking polished. A belted waist or a tailored fit ensures the dress stays flattering while maintaining a relaxed vibe. This style works wonderfully for daytime events, from brunches to garden parties, exemplifying old money style through its simplicity.
| Idea | Details |
|---|---|
| Best For | Brunches, garden parties, casual yet polished occasions |
| Fabric | Cotton |
| Key Accessories | Leather belt, simple bracelet, large sunglasses |
| Ideal Footwear | Loafers, ballet flats, espadrilles |
| Season | Spring and summer |
Peacoat Dress
A Peacoat Dress is a structured and fashionable option that embodies old money style while keeping you warm during the colder months. Made from thick wool, the peacoat dress has an oversized collar and double-breasted design, creating a polished, military-inspired look. Ideal for both formal and casual settings, this dress is chic and effortlessly elegant. Pair it with knee-high boots and a leather handbag to complete the look.
| Idea | Details |
|---|---|
| Best For | Winter events, formal occasions, business meetings |
| Fabric | Wool |
| Key Accessories | Leather handbag, knee-high boots, scarf |
| Ideal Footwear | Knee-high boots, leather ankle boots |
| Season | Fall and winter |
Maxi Dress in Tweed
A Maxi Dress in Tweed is a combination of classic sophistication and modern elegance. Tweed’s texture and richness provide an elevated look, while the maxi length adds a formal touch. Perfect for events like garden parties, afternoon weddings, or formal luncheons, this old money dress exudes timeless style. Tweed fabric ensures that the dress will last through seasons while maintaining its chic look. Pair it with leather gloves, a wide-brimmed hat, and elegant heels.
| Idea | Details |
|---|---|
| Best For | Garden parties, afternoon weddings, formal luncheons |
| Fabric | Tweed |
| Key Accessories | Wide-brimmed hat, leather gloves, pearl earrings |
| Ideal Footwear | Elegant heels, ballet flats |
| Season | Fall and winter |
Wool Overcoat and Suit: The Classic Laye
The wool overcoat is a must-have for anyone looking to maintain their old money dress look during colder months. It provides warmth while still keeping the outfit chic and polished.
- Material Selection: Wool is durable, timeless, and elegant. Choose a well-tailored overcoat that complements the suit underneath.
- Styling Tips: Pair with a tweed suit or flannel suit for optimal warmth and style. Dark-colored wool overcoats are best for versatility and classic appeal.
- Pro Tip: Make sure the overcoat’s length complements your suit and does not appear too bulky.
Perfect For: Cold-weather events, formal gatherings, and business travel.
Conclusion: Embracing Old Money Dress with Timeless Fashion Choices
The old money dress style is all about timeless elegance, quality craftsmanship, and understated luxury. By focusing on tailored fits, classic fabrics like tweed, wool, and cashmere, and accessories that exude refinement, you can easily embrace this sophisticated aesthetic.
Remember, the key to old money style is quality over flash—invest in timeless pieces that will never go out of style and make them your wardrobe essentials. With the right fashion items and an eye for detail, you’ll create a refined, classic wardrobe that stands the test of time.
As you experiment with these outfits, remember to keep your look subtle, polished, and effortlessly chic. The beauty of old money dress lies in its quiet luxury, and with these outfit ideas, you’ll embody this perfect balance of elegance and sophistication.