Timeless, refined, and effortlessly elegant—these are the hallmarks of the old money aesthetic. It’s more than just about what you wear; it’s about how you wear it, the understated confidence that comes with impeccable taste. Whether you’re dressing for a casual outing or a formal affair, the old money style is all about combining classic pieces with a modern twist. Let’s dive into how to master this look, one outfit at a time.
Timeless Casual Elegance
First, we’ll detail the Autumn look in this outfit. From the soft, neutral tones of the sweater to the clean lines of the fitted pants, this ensemble screams «old money.» The choice of materials is subtle but luxurious—high-quality wool and cotton are often the go-to for understated wealth. This look is practical for weekend brunch or an afternoon of book shopping, but it wouldn’t translate as well to Formal occasions.
- Sweater: Luxurious wool, soft beige, fitted but not tight.
- Pants: Light-colored trousers, adding to a casual elegance.
- Accessories: Understated leather watch, sleek sunglasses, casual loafers. Opinion: I wouldn’t change a thing about this look for Autumn. It’s perfect for those casual yet polished days. However, I’d steer clear of flashy belts or overly bold shoes, which would take away from the effortless vibe.
The Winter Power Move
This outfit is a masterclass in Winter layering. The classic Italian-cut suit underneath the wool overcoat demonstrates how to keep warmth while remaining stylish. The Aesthetic screams old-world charm, perfect for both business meetings and upscale dinners. The large leather bag hints at functionality without sacrificing sophistication.
- Coat: Wool, gray, mid-length, the perfect outer layer for colder months.
- Suit: Italian-cut, double-breasted, exuding sophistication.
- Bag: Leather, spacious, perfect for travel or business essentials. Opinion: For an elevated touch, a pocket square in a contrasting color could add some flair. However, I’d avoid overly colorful ties, as it could disrupt the sleek, neutral palette of this Winter ensemble.
Green Meets Sophistication
This look blends Casual comfort with impeccable style, a hallmark of old money fashion. The green cable-knit sweater offers a cozy yet refined look, while the crisp white shirt underneath provides structure. Perfect for a laid-back office day or even a Fall weekend outing.
- Sweater: Cable-knit, green, offering both texture and warmth.
- Shirt: White, tailored, peeking through the collar for that clean, sophisticated touch.
- Shoes: White sneakers, balancing casual with polish. Opinion: I’d add a darker belt for contrast and a watch with a leather strap. However, sneakers may not work in more Formal environments, so consider switching to loafers or oxfords for more formal settings.
Turtleneck and Tailoring
The turtleneck and tailored blazer combo is an essential in the old money Aesthetic. This particular look is perfect for transitional weather, especially in Fall or Autumn. The soft hues of cream pants with the darker blazer offer a balanced contrast, making the wearer look put-together without trying too hard. Perfect for an art gallery opening or an elegant lunch.
- Turtleneck: Dark green, soft wool, adding both warmth and sophistication.
- Blazer: Tailored fit, elevating the casualness of the turtleneck.
- Pants: Cream-colored, fitted, drawing the eye to the more structured top half. Opinion: I’d consider adding a patterned scarf for colder days. Avoid pairing this look with heavy boots, as the outfit works better with loafers or suede shoes.
Smart-Casual Done Right
This look brings together old money fashion and everyday comfort. The combination of a green quarter-zip sweater and beige pants keeps things Casual yet intentional, making it ideal for laid-back social gatherings or a stroll through the city in Fall. The brown shoes add a touch of formality without going overboard.
- Sweater: Green quarter-zip, cozy but stylish.
- Pants: Beige, straight-leg, classic fit.
- Shoes: Brown leather shoes, grounded and refined. Opinion: If I were to tweak this outfit, I might introduce a patterned undershirt to add visual interest. However, heavy jewelry or overly trendy sneakers wouldn’t mesh well with this clean, classic look.
Classic Layering with a Modern Twist
This first look brings together layers that epitomize autumn sophistication. The beige overcoat over a denim jacket instantly stands out as a versatile piece for transitional weather, seamlessly blending a rugged yet polished vibe. The use of denim under a structured coat not only adds depth but also gives the outfit a casual touch while keeping it structured enough for more formal settings. This is the kind of look that balances practicality with style, perfect for city streets or countryside weekends.
- Beige overcoat: Adds warmth and classic elegance, an essential for autumn and winter outfits.
- Denim jacket: Adds a relaxed, casual layer that contrasts well with the formal nature of the coat.
- White jeans: These slim-fit jeans elevate the entire ensemble, keeping it sharp without looking overly formal.
- Shoes: A pair of brown leather boots would round off this look, adding the perfect finishing touch for chilly weather.
For my opinion, I’d suggest experimenting with a darker wash denim for a more subtle look. A pair of leather gloves could also be a stylish and practical addition for cooler weather. What to avoid? Pairing this with athletic sneakers might detract from the refined aesthetic you’re aiming for.
Effortless Preppy Style
Here, we see the perfect embodiment of the old money preppy aesthetic—classic, clean, and ready for a day of leisure. A cream cable-knit sweater layered over a light blue button-down shirt exudes casual elegance without feeling overdone. It’s the perfect go-to look for an afternoon of tennis or brunch in the fall. This is a prime example of how to stay comfortable without sacrificing style, making it an ideal choice for casual outfits during fall and winter.
- Cable-knit sweater: Provides warmth while maintaining a clean, crisp look.
- Button-down shirt: The perfect layering piece that adds dimension to the overall outfit.
- Chinos: Opt for dark-colored chinos to keep the look grounded and sophisticated.
- Accessories: A classic pair of eyeglasses and a wristwatch add to the old-school charm.
In my opinion, a touch of Italian flair could be added by swapping the shoes for loafers or sleek leather dress shoes. One thing to avoid would be wearing overly distressed jeans or sneakers, as they would clash with the sophisticated vibe of this outfit.
Sleek City Formal
This outfit is the epitome of modern urban formal wear while still keeping that old-money elegance intact. The dark, tailored overcoat paired with grey trousers and crisp white sneakers perfectly balances formal and casual. This is the type of outfit that works well in a variety of settings—whether you’re heading to the office or grabbing a coffee on a brisk autumn day. It’s minimalistic, but each piece speaks volumes about timeless style.
- Overcoat: Charcoal grey and tailored, it gives off a polished vibe without being overly stiff.
- Turtleneck sweater: A black turtleneck is an excellent alternative to a shirt and tie for a more casual winter look.
- Trousers: Slim-fit grey trousers add a sleek element, perfect for both business and casual environments.
- White sneakers: These keep the look grounded in a casual, modern aesthetic while maintaining style.
While I love the modern twist of pairing sneakers with an otherwise formal look, I’d suggest trying a pair of Chelsea boots for a more dressed-up vibe. However, avoid adding bulky accessories like backpacks that would detract from the clean lines of this outfit.
Relaxed Elegance for Any Occasion
This outfit strikes the perfect balance between comfort and elegance, making it ideal for a laid-back yet polished look. The combination of light beige trousers and a crisp white long-sleeve tee brings out a casual and relaxed vibe, perfect for a Sunday brunch or even a casual meeting. The loafers, in particular, highlight the refined, minimalistic approach that the old money style often embraces.
- Long-sleeve tee: A fitted white shirt ensures that the look stays clean and polished.
- Beige trousers: These well-tailored trousers keep the outfit from feeling too casual while still offering comfort.
- Loafers: A suede pair of loafers complements the neutral tones, adding texture and style.
- Accessories: The understated wristwatch and aviators bring a classic touch to the look.
If you’re aiming for a more formal setting, I’d suggest swapping the tee for a button-up shirt or adding a structured blazer. Avoid oversized pieces that could make the look too casual or too slouchy.
Classic British Elegance
This look takes inspiration from traditional British heritage fashion, blending rustic charm with refined tailoring. The combination of a plaid flat cap, quilted vest, and leather boots gives off an unmistakably old money countryside vibe. It’s a look that works well for autumnal walks or even weekends at the estate—timeless yet rugged, making it an excellent choice for outdoor gatherings.
- Plaid flat cap: A quintessential part of old-money style, adding a touch of British countryside.
- Quilted vest: The olive-green vest provides both warmth and a vintage flair.
- Cable-knit sweater: Deep burgundy gives the outfit a rich, autumnal feel.
- Leather boots: These ankle-high boots are ideal for both style and practicality in cooler weather.
For a more formal spin, you could replace the vest with a tailored blazer and swap the boots for brogues. However, I’d avoid adding any brightly colored accessories, as they might clash with the more muted tones of the outfit.
Suave Simplicity: The Perfect Italian Blend
This look captures the essence of old money sophistication with a tailored wool jacket in a deep brown shade. The texture and cut of the jacket suggest an Italian influence, highlighting a preference for high-quality, classic tailoring. Paired with white jeans, it achieves a striking balance between relaxed and refined, making it suitable for a range of fall events, from casual dinners to more formal gatherings. The addition of a leather duffle bag in dark brown further enhances the luxurious, understated vibe of the outfit.
- Wool jacket: Tailored perfectly, the jacket gives structure to the outfit while maintaining a relaxed, effortless feel.
- White jeans: A bold yet classic choice for fall, these jeans offer a smart contrast to the deeper tones of the jacket.
- Leather duffle bag: The engraved initials add a personal, old-money touch, while the suede texture exudes quiet luxury.
- Brown suede shoes: Coordinating seamlessly with the jacket and bag, these shoes ground the outfit with their rich, autumnal tone.
To enhance this look, a pair of black gloves could add an extra layer of polish, perfect for the colder months. However, adding more accessories could detract from its simple elegance—so avoid flashy belts or watches.
Elevated Casual: Comfortable Elegance
This second look is all about casual sophistication with a vintage touch. The loose beige sweater paired with blue jeans immediately evokes a relaxed yet put-together look—ideal for a brisk autumn walk or a laid-back weekend outing. While the sweater might seem casual, the crisp shirt underneath and leather jacket slung over the shoulder add just enough formality to give it that old-money charm.
- Beige sweater: Soft, oversized, and perfect for layering, this piece combines comfort with style.
- Blue jeans: Fitted but not tight, these jeans bring a laid-back vibe to the outfit, making it great for casual outfits.
- Leather boots: Adding a rugged touch to the otherwise simple ensemble, these shoes are both practical and stylish for autumn weather.
- Wristwatch: A classic timepiece peeking out from under the cuff signals subtle luxury without trying too hard.
A scarf in a muted autumn color would complement the palette here, while swapping the jeans for tailored trousers could make this outfit more formal. However, stay clear of anything too bright or patterned, as it might clash with the overall tone.
Layered Luxury: Autumn and Winter Perfection
Here we see the pinnacle of old money aesthetic layering. A quilted vest in khaki worn over a navy blue sweater perfectly balances utility with style, evoking an air of country sophistication. The look is completed with ivory trousers and sturdy brown boots, making it ideal for everything from a fall country retreat to an evening by the fire.
- Quilted vest: Functional and stylish, this outer layer adds warmth without sacrificing elegance.
- Navy blue sweater: The deep navy adds depth to the look, offering a perfect backdrop for the lighter tones of the vest.
- Ivory trousers: Clean and refined, these trousers are both relaxed and dressy, making them suitable for both day and night.
- Brown leather boots: Rugged yet refined, these boots are perfect for navigating both country estates and urban streets.
Adding a lightweight scarf in a complementary color would be perfect for chilly autumn evenings. However, avoid wearing anything too casual, like sneakers, as it would diminish the refined nature of this outfit.
Timeless Beige: The Classic Suit Look
This look is pure formal old money chic. A beige double-breasted jacket paired with tailored black trousers is perfect for warmer autumn days when you need to dress up without overdoing it. The minimalistic approach is what gives this outfit its charm, especially when paired with a classic white pocket square and understated loafers.
- Beige jacket: The double-breasted cut adds structure, while the light color keeps it fresh for autumn.
- Black trousers: Tailored and sleek, they create a formal yet approachable aesthetic.
- White pocket square: A subtle touch that speaks volumes about attention to detail.
- Loafers: In keeping with the old money look, they’re stylish without being flashy.
Adding a black tie could elevate this outfit for a more formal occasion. However, avoid anything too bold—this outfit works because of its understated elegance.
Modern Italian Meets Heritage Style
A tan shearling jacket paired with a black turtleneck and black jeans is the perfect combination of modern luxury and classic heritage. This outfit is ideal for winter outings, providing warmth without sacrificing style. The shearling adds texture, while the black base keeps it sleek and polished.
- Tan shearling jacket: Warm, luxurious, and effortlessly stylish.
- Black turtleneck: A winter staple that adds sophistication to any outfit.
- Black jeans: Slim but not tight, perfect for creating a streamlined silhouette.
- Leather boots: In a rich chestnut, these boots contrast nicely with the darker tones and elevate the entire look.
Adding a wool scarf in a neutral color would make this outfit even cozier for winter. Avoid any flashy accessories that would take away from the timeless feel of the shearling jacket.
Old money style is all about timeless elegance, blending classic pieces with a modern touch. Whether you’re dressing for autumn, winter, or a casual outing, this look speaks of refined taste and confidence. Drop a comment and let us know how you’re planning to incorporate these timeless elements into your wardrobe!
