“Old Money” is a timeless tradition of elegance, sophistication, and understated luxury for the men. Combining quality craftsmanship with easily interpreted, neutral tones without ever leaving character out.
It is a look guaranteed to stand the test of time-a perfect winter look that combines comfort with class, from wool overcoats to cashmere sweaters and structured blazers, all staple pieces that form the foundation of the old-money wardrobe. Be it a formal event or a casual date, these 44 winter outfits show up the epitome of Old Money charm with a twist of new appeal.
1. Classic Wool Overcoat Elegance
Wrap yourself in timeless sophistication with a perfectly tailored wool overcoat. These coats, in neutral tones like camel or navy, exude wealth without shouting it. Layer over a cashmere sweater for an effortlessly refined look that whispers old-world class. Paired with slim-fit wool trousers, it offers a balance between luxury and function.
Top: Cashmere crew-neck sweater, soft to the touch with understated warmth.
Bottom: Tailored wool trousers, neatly pressed, and perfectly fitted.
2. Cable-Knit Sweater Charm
A soft, chunky cable-knit sweater adds a sense of heritage to any winter wardrobe. Choose earthy tones like cream, olive, or rust for that old-money feel. Layer it over a crisp white shirt for a polished look or wear it alone for a more casual take on elegance. Paired with classic chinos, it brings laid-back sophistication to life.
Top: Thick cable-knit sweater, perfectly oversized for comfort and casual elegance.
Bottom: Classic beige chinos, cuffed at the ankle for a neat, relaxed vibe.
3. Tailored Blazer and Turtleneck Ensemble
This iconic combination of a tailored blazer and a fitted turtleneck screams quiet wealth. Opt for a wool or tweed blazer in neutral or muted tones for that timeless old-money look. The turtleneck, in shades of deep navy, grey, or black, adds an intellectual edge. Pair with tailored wool trousers or dark chinos for a flawless finish.
Top: Slim-fit turtleneck, providing warmth and a refined silhouette.
Bottom: Dark wool trousers, sharply tailored to complete the polished look.
4. Heritage Tweed Suit
Tweed suits stand the test of time, an ode to gentlemanly elegance. The intricate patterns, like herringbone or houndstooth, speak of tradition and heritage. Opt for a three-piece suit to truly embody the old-money aesthetic, adding a waistcoat for extra charm. The suit pairs perfectly with polished oxford shoes and a crisp white shirt.
Top: Tailored tweed blazer with a matching vest for that extra layer of class.
Bottom: High-waisted tweed trousers, slim and polished with vintage appeal.
5. Cashmere Scarf and Overcoat Combo
A cashmere scarf draped over a luxurious overcoat instantly upgrades any outfit. Opt for understated patterns like subtle plaid or solid colors such as burgundy or charcoal. Paired with a classic double-breasted overcoat, this combo creates a striking yet understated silhouette.
Top: Double-breasted wool overcoat, exuding timeless style with its structured fit.
Bottom: Slim-fit trousers in a dark, neutral shade, grounding the elegance of the top layers.
6. Velvet Blazer for Evening Glamour
Velvet blazers offer a soft touch of opulence to any formal event. Deep jewel tones like emerald, burgundy, or navy exude luxury without being ostentatious. Worn over a crisp white shirt with a silk tie, it captures both tradition and contemporary flair. Paired with tailored black trousers, the look transitions effortlessly from dinner to after-hours.
Top: Rich velvet blazer in a dark jewel tone, making a subtle yet memorable statement.
Bottom: Crisp black trousers, tapered at the ankle for a sharp finish.
7. Vintage Fair Isle Sweater
Fair Isle sweaters, with their intricate knitting patterns, invoke a sense of tradition and coziness. Choose muted colors or earth tones to maintain a classic, old-money appearance. Layer it under a wool overcoat or pair it with corduroy trousers for a relaxed winter weekend look.
Top: Fair Isle sweater, knitted with a blend of intricate patterns and earthy tones.
Bottom: Corduroy trousers, providing warmth and a rustic feel to complement the sweater.
8. Houndstooth Overcoat Authority
A houndstooth patterned overcoat immediately adds structure and depth to any winter outfit. Its distinct black-and-white pattern creates visual interest, while its wool fabric ensures warmth. Pair it with a simple turtleneck or cashmere sweater underneath for a streamlined look.
Top: Houndstooth overcoat, tailored sharply for a commanding silhouette.
Bottom: Dark wool slacks, creating a subtle backdrop for the bold overcoat.
9. Layered Peacoat Perfection
The peacoat is a staple for the old-money winter wardrobe, embodying military elegance. Opt for navy or black to keep things timeless. Layer it over a chunky knit sweater and scarf for added warmth and texture. Complete the look with fitted trousers or dark denim for an effortless combination.
Top: Classic navy peacoat, double-breasted for a structured, sophisticated look.
Bottom: Slim-fit trousers or dark denim for a modern touch to the classic silhouette.
10. Dapper Double-Breasted Blazer
Nothing speaks of timeless wealth like a double-breasted blazer. Its tailored fit and commanding shape exude confidence. Opt for rich fabrics like wool or cashmere in classic colors such as navy, charcoal, or deep green. Pair with a slim-fit turtleneck underneath for a seamless winter look.
Top: Double-breasted wool blazer that provides structure and elegance.
Bottom: Slim-fit trousers in a coordinating shade for a cohesive and polished appearance.
11. Cashmere and Wool Knit Layers
For an understated yet luxurious look, combine cashmere and wool layers in neutral shades. A wool vest worn over a cashmere turtleneck adds both texture and warmth. Pair with wool slacks for an all-over sophisticated winter ensemble.
Top: Wool vest layered over a cashmere turtleneck for a sophisticated winter ensemble.
Bottom: Wool slacks, creating a seamless transition from top to bottom.
12. Sophisticated Camel Coat
The camel coat has long been a symbol of understated wealth. Its warm, neutral tone complements virtually any outfit while its length and structure exude confidence. Layer it over a turtleneck or button-up shirt for a sharp winter look. Paired with slim wool trousers, the result is timeless elegance.
Top: Camel overcoat, providing an effortlessly elegant silhouette.
Bottom: Slim-fit wool trousers in grey or navy for contrast and balance.
13. Corduroy Jacket Sophistication
A corduroy jacket offers a warm yet refined option for winter wear. Opt for rich earth tones like olive, deep brown, or rust for that old-money allure. Layer over a merino wool turtleneck or cashmere sweater for added texture. Pair the jacket with slim-fit trousers or dark denim for a polished finish.
Top: Corduroy jacket, adding texture and warmth with its rich, tactile fabric.
Bottom: Slim-fit trousers in dark, neutral tones to balance the rustic jacket.
14. Cashmere Rollneck and Trench Coat
The combination of a cashmere rollneck sweater and a classic trench coat oozes refined sophistication. Stick to neutral colors like cream or grey for the sweater, paired with a camel or khaki trench coat for timeless appeal. Pair with tailored trousers and polished shoes for a complete old-money vibe.
Top: Cashmere rollneck sweater, soft and luxurious with a minimalist appeal.
Bottom: Tailored trousers, sharp and neat, creating a balance with the flowing trench coat.
15. Turtleneck Underneath a Suit Jacket
One of the simplest ways to add an old-money touch to your winter wardrobe is by swapping a dress shirt for a turtleneck underneath your suit jacket. This combination offers both warmth and sleek sophistication. Opt for a neutral or dark-colored turtleneck to contrast with a wool suit in navy, grey, or deep green.
Top: Fitted wool suit jacket over a minimalist turtleneck, blending structure with softness.
Bottom: Matching wool trousers, sharp and tapered for a cohesive, clean silhouette.
16. Puffer Vest and Wool Trousers Duo
For a modern take on old-money style, try a puffer vest layered over a wool sweater. The puffer vest adds a sporty edge without sacrificing the sophisticated vibe. Opt for muted colors like navy or olive, pairing it with dark wool trousers to maintain balance.
Top: Puffer vest over a wool sweater, blending warmth with an athletic touch.
Bottom: Dark wool trousers, maintaining the timeless and refined appeal.
17. Plaid Scarf and Wool Peacoat Combo
A plaid scarf instantly elevates any winter outfit, especially when paired with a well-tailored wool peacoat. Opt for classic tartan or houndstooth patterns for a nod to old-world charm. The peacoat provides structure, while the scarf adds a pop of color and texture. Together, they create a harmonious blend of classic winter style.
Top: Wool peacoat, double-breasted for structure, layered with a plaid scarf for added flair.
Bottom: Slim wool trousers, offering a tailored finish to the structured peacoat.
18. Quilted Jacket and Corduroy Pants
A quilted jacket in muted tones like olive, navy, or charcoal adds a subtle touch of old-money charm. Paired with corduroy trousers, it strikes the perfect balance between rugged and refined. The quilted texture brings an element of warmth and casual sophistication, making it ideal for outdoor activities or countryside getaways.
Top: Quilted jacket, understated and functional with a hint of vintage flair.
Bottom: Corduroy trousers in deep brown or burgundy, complementing the rustic jacket.
19. Wool Trench Coat with Leather Gloves
Few winter outfits exude as much quiet elegance as a wool trench coat paired with high-quality leather gloves. The trench coat, in classic colors like charcoal or camel, offers a long, sweeping silhouette that conveys authority. Leather gloves, in dark brown or black, add a luxurious touch without being overt.
Top: Wool trench coat, creating a dramatic yet polished winter silhouette.
Bottom: Slim-fit wool trousers or dark denim, keeping the overall look refined and balanced.
20. Classic Crewneck Sweater with Chinos
A classic crewneck sweater made from cashmere or fine wool embodies understated luxury. Choose neutral colors like heather grey, navy, or cream for a timeless feel. Paired with chinos, this outfit is perfect for casual winter gatherings or relaxed evenings at home.
Top: Cashmere crewneck sweater, softly fitted for a sleek and relaxed feel.
Bottom: Tailored chinos, rolled slightly at the ankle for a modern, laid-back vibe.
21. Wool Overcoat with Leather Boots
A long wool overcoat paired with polished leather boots instantly elevates any winter ensemble. The coat, preferably in dark shades like navy or charcoal, provides structure and warmth, while leather boots add an element of rugged sophistication. This look works well for both formal and casual settings, especially when paired with slim-fit trousers or dark jeans.
Top: Long wool overcoat, fitted and tailored for a structured look.
Bottom: Slim-fit trousers or dark jeans paired with polished leather boots, creating a rugged-meets-refined vibe.
22. Glen Plaid Suit with Rollneck Sweater
A Glen plaid suit combined with a rollneck sweater offers a refined take on traditional winter suiting. The subtle plaid pattern adds texture and depth, while the rollneck replaces the standard dress shirt for a more contemporary feel. Ideal for formal occasions where warmth and style are equally important.
Top: Glen plaid suit jacket over a fitted rollneck sweater for a perfect blend of textures.
Bottom: Tailored plaid trousers, sharp and cohesive with the overall ensemble.
23. Chunky Turtleneck with Wool Overcoat
A chunky turtleneck sweater paired with a wool overcoat creates an elegant yet cozy winter look. The sweater, in shades like cream, grey, or deep burgundy, provides warmth and a relaxed silhouette. The wool overcoat, long and tailored, adds structure and sophistication.
Top: Chunky turtleneck sweater, oversized for warmth and comfort.
Bottom: Tailored wool trousers or dark jeans, balancing the relaxed top with a sharp finish.
24. Tailored Wool Suit with Scarf
A tailored wool suit paired with a soft cashmere scarf is the epitome of old-money elegance. The suit, in classic colors like navy or grey, exudes quiet sophistication. The scarf adds warmth without sacrificing style. Together, they create a flawless winter look that transitions easily from business to social gatherings.
Top: Tailored wool suit jacket, sleek and structured, layered with a soft scarf.
Bottom: Matching wool trousers, sharply tailored to maintain a cohesive look
25. Double-Breasted Blazer with Turtleneck
For a sophisticated winter look, pair a double-breasted blazer with a classic turtleneck sweater. The blazer’s structured design offers an air of authority, while the turtleneck introduces an element of relaxed elegance. Choose a dark wool blazer in navy, grey, or charcoal and a turtleneck in a contrasting yet neutral shade.
Top: Double-breasted blazer, structured and sharp, layered over a turtleneck for warmth.
Bottom: Tailored wool trousers in a matching or complementary color for a balanced, polished finish.
26. Houndstooth Coat with Chelsea Boots
A houndstooth coat immediately gives off old-money vibes with its timeless pattern and classic silhouette. Pair this coat with sleek Chelsea boots for a modern yet elegant winter ensemble. The coat’s pattern stands out, so opt for solid, neutral pieces underneath—perhaps a cashmere sweater and dark chinos or trousers.
Top: Houndstooth coat, bold in pattern yet refined in structure, ideal for cold winter days.
Bottom: Slim-fit trousers or dark chinos, keeping the focus on the coat’s pattern while maintaining a tailored fit.
27. Peacoat and Turtle-Neck Combo
The classic peacoat layered over a cozy turtleneck sweater offers a warm yet stylish winter ensemble. Opt for a wool peacoat in dark colors like navy, black, or charcoal and pair it with a soft turtleneck in cream or grey. This combination blends structure with comfort, making it perfect for weekend outings or casual dinners.
Top: Wool peacoat over a snug turtleneck, adding warmth with a tailored silhouette.
Bottom: Slim-fit dark trousers or jeans, providing balance to the structured peacoat.
28. Camel Overcoat and Slim-Fit Jeans
The camel overcoat is an old-money staple for the winter season, offering timeless elegance and warmth. Pair it with slim-fit jeans for a balanced look that mixes casual and formal elements. The coat’s neutral, warm tones complement a wide range of outfits, but dark jeans and a wool or cashmere sweater underneath create a refined, laid-back ensemble.
Top: Camel overcoat, long and sleek, offering warmth and sophistication.
Bottom: Slim-fit jeans, casual but fitted, providing contrast to the formality of the coat.
29. Monochrome Layering
Achieve a minimalist, old-money look by layering various shades of the same color. Start with a base layer, such as a turtleneck sweater, and add a wool blazer or coat in a similar but slightly darker hue. Pair with polished leather shoes for a clean finish.
Top: Wool blazer or coat, layered over a similarly colored turtleneck or sweater.
Bottom: Tailored wool trousers, matching in tone, ensuring a seamless, elegant look.
30. Shearling Collar Jacket with Wool Trousers
The shearling collar jacket brings a rugged, yet sophisticated edge to any winter wardrobe. Opt for a wool or leather jacket with a shearling-lined collar for both warmth and style. Pair this jacket with tailored wool trousers for a polished look that still has a touch of old-world charm.
Top: Shearling collar jacket, combining rugged warmth with classic style.
Bottom: Tailored wool trousers, offering a sophisticated contrast to the jacket’s rustic appeal.
31. Plaid Shirt with Cashmere Cardigan
A plaid shirt layered under a cashmere cardigan offers a relaxed, old-money vibe with a touch of rustic charm. The plaid pattern brings a casual element, while the soft cashmere adds a layer of luxury. Perfect for weekend getaways or casual winter dinners, this look combines comfort and style seamlessly. Pair with dark denim or corduroy trousers for a complete look.
Top: Plaid shirt, casual and earthy, layered beneath a luxurious cashmere cardigan.
Bottom: Corduroy or dark denim trousers, grounding the look in casual elegance.
32. Military-Inspired Coat with Scarf
A military-inspired wool coat adds structure and authority to any winter outfit. Pair it with a soft scarf in a neutral color for a touch of warmth and elegance. The coat’s strong lines and buttons make it a statement piece, so keep the rest of the outfit simple—perhaps a plain turtleneck and tailored trousers.
Top: Military-inspired coat, structured and commanding, with a soft scarf for contrast.
Bottom: Tailored trousers, sharp and simple, maintaining the coat as the focal point.
33. Leather Jacket with Wool Scarf
A leather jacket paired with a wool scarf offers a sleek, modern twist on old-money style. The leather jacket adds an element of edginess, while the wool scarf softens the look, providing warmth and texture. Choose a dark leather jacket in black or brown, and pair it with a neutral or patterned wool scarf.
Top: Leather jacket, sleek and modern, with a wool scarf for added warmth and texture.
Bottom: Slim-fit jeans or wool trousers, keeping the look sharp and streamlined.
34. Cable-Knit Sweater and Wool Coat
A classic cable-knit sweater paired with a long wool coat exudes winter sophistication. The texture of the cable-knit sweater adds depth and warmth, while the wool coat provides structure and elegance. This combination works well for both casual and formal occasions, depending on the accessories and trousers you choose.
Top: Cable-knit sweater, cozy and textured, layered under a long wool coat for warmth.
Bottom: Tailored wool trousers or slim jeans, offering balance to the bulky sweater.
35. Suede Bomber Jacket with Turtleneck
A suede bomber jacket adds a luxurious yet laid-back vibe to any winter outfit. Layer it over a turtleneck sweater for a sleek, modern look with old-money roots. Choose a suede jacket in neutral tones like camel, grey, or brown, and pair it with a turtleneck in a contrasting shade.
Top: Suede bomber jacket, offering a touch of luxury with a relaxed silhouette.
Bottom: Dark slim-fit trousers or denim, maintaining a polished yet casual aesthetic.
36. Wool Blazer with Cashmere Turtleneck
A wool blazer layered over a cashmere turtleneck is a classic winter look for those who appreciate old-money style. The wool blazer provides structure, while the cashmere turtleneck adds softness and warmth. Stick to neutral tones like grey, navy, or camel for the blazer, paired with a cream or grey turtleneck.
Top: Wool blazer, structured and sharp, layered over a soft cashmere turtleneck.
Bottom: Tailored trousers or dark jeans, keeping the look cohesive and refined.
37. Polo Neck with Trench Coat
A polo neck layered under a tailored trench coat creates a classic and refined winter look. The trench coat’s long silhouette brings elegance, while the polo neck introduces warmth without bulk. Opt for neutral or dark tones—navy, grey, or camel—for a sophisticated, old-money appeal.
Top: Tailored trench coat, lightweight yet warm, layered over a simple, fitted polo neck.
Bottom: Slim trousers or dark jeans, ensuring a streamlined silhouette beneath the long coat.
38. Herringbone Tweed Blazer with Button-Down Shirt
The herringbone tweed blazer embodies old-money charm, making it a must-have for winter style. Layer it over a crisp button-down shirt for a sharp, polished look. The texture of the tweed brings depth, while the shirt keeps the ensemble clean and tailored.
Top: Herringbone tweed blazer, textured and rich, layered over a crisp, structured button-down.
Bottom: Wool trousers or chinos, providing contrast in texture while maintaining a refined feel.
39. Chunky Knit Sweater with Wool Trousers
A chunky knit sweater paired with tailored wool trousers blends casual comfort with polished sophistication. The thick, textured sweater keeps you warm, while the wool trousers add structure to balance the outfit. Opt for neutral shades like cream, grey, or navy for a timeless feel.
Top: Chunky knit sweater, rich in texture and warmth, perfect for cold winter days.
Bottom: Tailored wool trousers, providing structure and a polished contrast to the sweater’s bulk.
40. Quilted Vest Over Button-Down Shirt
For a smart, layered look, wear a quilted vest over a button-down shirt. The vest offers warmth without adding bulk, while the shirt keeps the look clean and refined. This combination works well for casual winter outings or countryside retreats. Add slim-fit jeans or chinos to complete the ensemble.
Top: Quilted vest, lightweight yet warm, layered over a crisp button-down shirt.
Bottom: Slim-fit jeans or chinos, casual yet polished, complementing the vest’s practical style.
41. Wool Coat with Fair Isle Sweater
A wool coat paired with a Fair Isle sweater creates a cozy yet distinguished winter look. The traditional Fair Isle pattern adds a touch of rustic charm, while the wool coat keeps the outfit polished. Opt for a coat in navy, grey, or camel, and a sweater with a subtle, classic pattern.
Top: Wool coat, long and sleek, layered over a patterned Fair Isle sweater for added warmth.
Bottom: Dark trousers or jeans, grounding the outfit with a streamlined, casual touch.
42. Corduroy Blazer with Cashmere Scarf
A corduroy blazer paired with a soft cashmere scarf exudes casual winter luxury. The corduroy adds texture and warmth, while the scarf brings an extra layer of elegance. Opt for a neutral or earth-toned blazer like olive, brown, or navy and a scarf in a contrasting yet complementary color.
Top: Corduroy blazer, rich in texture, with a soft cashmere scarf adding sophistication.
Bottom: Dark jeans or wool trousers, keeping the outfit grounded in casual elegance.
43. Tweed Overcoat with Leather Gloves
A tweed overcoat, paired with leather gloves, embodies a timeless winter look with a touch of old-world charm. The texture of the tweed adds depth, while the leather gloves introduce a sleek, modern element. Choose a long overcoat in traditional tweed patterns like houndstooth or herringbone, and pair with dark leather gloves.
Top: Tweed overcoat, textured and rich, complemented by sleek leather gloves for contrast.
Bottom: Tailored trousers or dark wool pants, maintaining the refined tone of the overcoat.
44. Cashmere Sweater with Peacoat
The classic peacoat paired with a soft cashmere sweater is a winter wardrobe essential for old-money style. The peacoat’s structured design adds formality, while the cashmere sweater brings warmth and comfort. Stick to neutral colors navy, black, or charcoal for the peacoat and cream or grey for the sweater.
Top: Peacoat, structured and classic, layered over a luxurious cashmere sweater.
Bottom: Tailored wool trousers or slim-fit jeans, ensuring the overall look remains polished.