Discover 40+ classy, elegant, expensive-looking, and comfy styles that redefine winter fashion. Elevate your wardrobe this season!
As the crisp air of winter settles in, a particular allure envelops the season, inviting us to wrap ourselves in layers of luxury and comfort.
While trends may come and go like fleeting snowflakes, the charm of old money style remains timeless—an artful blend of elegance that whispers sophistication without ever shouting for attention.
Imagine stepping into a world where every piece is crafted with care, each fabric hand-selected for its quality and durability, echoing generations of refined taste.
In this curated collection of 40+ old money winter outfits, we delve deep into the essence of understated glamour.
From sumptuous cashmere sweaters paired with tailored trousers to impeccably cut overcoats draping effortlessly over classic wool skirts, these ensembles embody a lifestyle steeped in grace.
This post is all about old money winter outfits.
How to Dress Old Money for Winter
Classy All-Black Outfits
@mimiarr
@sophiepirrung
When it comes to crafting a classy all-black outfit, the allure lies not just in simplicity but in the artful interplay of textures and silhouettes.
A well-tailored black turtleneck paired with high-waisted wool trousers can create a refined silhouette that channels timeless elegance.
Elevate this look further with an oversized cashmere coat, allowing you to add layers without losing sophistication.
Accessories like a structured leather handbag or statement silver jewelry punctuate the darkness, adding interest and elevating your style quotient.
Consider embracing unique fabric choices; think sleek leather alongside soft satin.
A long black pleated skirt cascading gracefully from the waist can inject movement into an otherwise static palette while retaining an air of sophistication suitable for any winter gathering.
Footwear also plays a crucial role; opting for chic boots or loafers with delicate embellishments can pull together your ensemble flawlessly, proving that even within one color scheme, there’s room for personal expression and flair.
Elegant Black and White Outfits
@aidabadji_
The timeless allure of elegant black and white outfits transcends seasons, making them a staple in any old-money wardrobe.
These monochromatic ensembles exude sophistication while remaining effortlessly chic, perfect for winter outings.
Imagine layering a tailored black cashmere coat over a crisp white blouse paired with high-waisted trousers; this versatile combination not only brings warmth but also highlights the wearer’s silhouette with an air of confidence.
To elevate your look further, consider incorporating luxurious textures such as velvet or silk into your outfit.
A flowing white silk scarf can soften the rigid lines of structured pieces and add visual interest, while intricate lace details lend an unexpectedly romantic touch to classic styles.
Classic Brown and Black Combo
The classic combination of brown and black has long been a cornerstone of sophisticated style, exuding an air of understated elegance.
This pairing offers a richness that can transform even the simplest winter ensemble into something truly special.
Imagine a tailored black wool overcoat layered over a chocolate cashmere turtleneck, paired with dark chocolate trousers—this timeless look not only keeps you warm but also showcases the beauty of texture and color contrast.
Accessories, such as a sleek black leather belt or suede ankle boots, further elevate the outfit while maintaining its classic appeal.
Embracing this duo allows for versatility in your winter wardrobe; it can effortlessly transition from day to night with just a few thoughtful adjustments.
Add statement jewelry in gold tones or bright silk scarves for pops of color without overwhelming the sophisticated foundation established by browns and blacks.
Elevate Your Sneakers Looks
@sophiepirrung
While sneakers are often associated with casual wear, integrating them into an old money aesthetic can elevate your style to impressive heights.
To achieve this, opt for classic sneaker designs in neutral shades or subtle patterns.
A pair of white leather sneakers paired with tailored trousers and a cashmere sweater instantly transforms a basic outfit into something refined yet approachable.
Don’t shy away from experimenting with textures; consider pairing suede sneakers with woolen pieces for added depth.
White Wide Leg Pants to Brighten Your Winter Wardrobe
@cocobeautea
@sophiepirrung
White wide-leg pants are a standout piece that can elevate your winter wardrobe, bringing an unexpected brightness to the typically muted palette of the season.
The flowing fabric creates a sophisticated silhouette that exudes elegance while ensuring comfort—a perfect analogy for the old money aesthetic.
Pair these versatile bottoms with a turtleneck or cashmere sweater in rich jewel tones to strike a balance between warmth and style.
A tailored overcoat draped nonchalantly over your shoulders can add layers and dimension, ultimately creating an effortlessly polished look.
For those chilly days, a stylish scarf in soft neutrals complements your crisp white ensemble, maintaining an air of refinement while keeping you cozy.
Chanel-Inspired Jacket Looks
The Chanel-inspired jacket is more than just a piece of clothing; it’s a symbol of timeless elegance that seamlessly transitions from season to season.
Layering a lightweight cashmere turtleneck beneath the jacket not only adds warmth but creates a sophisticated silhouette that exudes understated luxury.
Accessorizing with vintage-inspired brooches and pearl earrings can further elevate your look, infusing it with a touch of nostalgia while remaining firmly in the realm of modernity.
Footwear choices matter too; opt for sleek leather ankle boots or classic loafers to maintain an air of refined comfort.
For those colder days, drape a stylish plaid scarf over your shoulders—this combination embraces old-money aesthetics while providing practicality against chillier winds.
Add a Red Bag to All Grey Outfits
Grey exudes sophistication but can sometimes veer into monotony; introducing a bold red bag elevates your look, adding just the right amount of playfulness without compromising on class.
The contrast between the soft, neutral tones and striking cherry or deep burgundy hue ignites intrigue and draws attention to your outfit’s center—the curated balance of old money chic.
When selecting your red bag, consider both texture and style; a structured leather tote imbues serious undertones while a slouchy crossbody invites casual sophistication.
Pairing this pop of color with delicate gold accents or simply understated jewelry allows for seamless integration into your glow-up Winter wardrobe.
Classic Black and Grey Combo
@sophiepirrung
The classic black and grey combo epitomizes timeless elegance, making it a staple in any old money wardrobe.
This sophisticated pairing is perfect for winter, as its muted tones work harmoniously to create a sleek silhouette that exudes effortless style.
To elevate this combination, consider incorporating textures like cashmere or wool; a finely knit black turtleneck paired with a tailored grey overcoat can achieve an enviable look that’s both chic and cozy.
Accessories play a pivotal role in enhancing this palette—imagine complementing your ensemble with rich leather gloves or a luxurious scarf in varying shades of gray.
Layering becomes an art form here; use different shades and fabrics to add depth while maintaining harmony.
Fur or Faux Fur Coat
Pairing fur or faux fur with tailored wool trousers or over a chic holiday dress instantly elevates an outfit into the realm of high fashion while reflecting modern sensibilities.
Whether you opt for romantic curves or sharp silhouettes, both options seamlessly integrate into your old-money-inspired winter wardrobe—inviting warmth and elegance while asserting individual ethics in style choices.
Mix and Layer Different Shades of Brown
Mixing and layering different shades of brown can transform your winter wardrobe into a sophisticated palette that exudes both warmth and elegance.
Embrace earthy tones like rich chocolate, muted taupe, and soft caramel for a look that feels cozy yet refined.
Start with a base layer, perhaps a classic brown turtleneck or cashmere sweater, which not only adds insulation but also serves as the perfect canvas for bolder accents.
Pair it with high-waisted, tailored pants in a lighter shade to create an elegant silhouette that elongates the legs.
Accessories play a crucial role in this harmonious color scheme; consider adding textured elements such as suede boots or leather gloves to infuse depth into your outfit.
A patterned scarf featuring various brown hues can introduce visual interest without overwhelming the overall look—think stripes or subtle plaids that bring together different tones seamlessly.
Mix White and Beige
Mixing white and beige is a timeless approach that effortlessly embodies the understated elegance synonymous with old money aesthetics.
This color pairing not only evokes a sense of sophistication but also embraces a calming, neutral palette that’s perfect for winter layering.
Imagine a crisp, tailored white wool coat over a soft beige cashmere turtleneck paired with high-waisted trousers in creamy ivory; this look speaks to luxurious comfort while remaining polished.
What truly elevates this duo is its versatility—consider adding textured elements like an ivory cable-knit scarf or taupe suede ankle boots to add dimension without overwhelming the simplicity of the palette.
Accents of gold jewelry can subtly enhance the warmth of these hues and introduce a touch of opulence that aligns perfectly with old money principles: less is indeed more.
Sleek Knee High Boots
@sophiepirrung
Knee-high boots effortlessly epitomize sophistication, serving as a versatile foundation for your winter wardrobe.
Their sleek silhouette elongates the leg, making them a flattering choice that complements everything from tailored trousers to flowing midi dresses.
Opt for materials like buttery leather or rich suede in classic shades of black, deep brown, or even an unexpected navy to align with the understated elegance characteristic of old money style.
These boots are not just a statement piece; they embody an ethos of timeless luxury.
Pair them with textured wool skirts and oversized cashmere sweaters for an elevated yet cozy look ideal for winter gatherings.
For a more refined touch, consider layering them under tailored coats featuring intricate craftsmanship—think softened shoulders and double-breasted buttons—to create a seamless flow that exudes effortless finesse.
Classic Black Loafers
@sophiepirrung
@cocobeautea
Classic black loafers are a cornerstone of the old money aesthetic, seamlessly bridging the gap between sophistication and comfort.
Their sleek, understated design exudes an effortless elegance that effortlessly elevates any winter outfit.
Whether paired with tailored trousers for a polished office look or styled with timeless cashmere sweaters and pleated skirts for weekend outings, these shoes always deliver a touch of refinement.
The beauty of loafers lies not just in their form but also in their versatility—making them suitable for both formal gatherings and casual brunches alike.
Wear a Sleek Belt
Incorporating a sleek belt into your winter outfit is a subtle yet powerful way to elevate your look.
A minimalist leather belt can cinch the waist of oversized coats or tailored blazers, creating an hourglass silhouette that adds structure to any ensemble.
Opt for understated colors like navy, deep brown, or classic black to maintain the timeless vibe that old money style embodies.
Moreover, consider experimenting with unique buckles or textures—perhaps a matte finish or a delicate gold accent—that can serve as focal points without overpowering the overall aesthetic.
This small accessory not only enhances your figure but also speaks volumes about attention to detail and refined taste.
Paired with high-waisted trousers or flowing skirts, a sleek belt can effortlessly tie together layers while providing functionality and flair during chilly days.
Embrace the Scarf Coat Trend
@cocobeautea
The scarf coat trend is an elegant fusion of comfort and sophistication, perfect for enhancing your winter wardrobe.
This unique piece, which combines the practicality of a classic coat with the plush softness of a cozy wrap, allows you to effortlessly elevate your style while embracing that luxurious old money aesthetic.
Imagine wrapping yourself in a wool or cashmere blend scarf coat, its fluid silhouette draping gracefully around you like an embrace from winter itself.
Pair it with tailored trousers or an A-line skirt to achieve that refined look reminiscent of upper-crust gatherings in chilly climates.
The versatility of the scarf coat means it can be layered over fine knits or even used as a chic alternative to traditional outerwear at more formal events; this easy adaptability makes it not just a trend but a staple.
Wear Wide Leg Jeans
@sophiepirrung
Wide leg jeans are an unexpected yet chic addition to any winter wardrobe, perfectly embodying the old money aesthetic’s blend of elegance and comfort.
Unlike typical skinny jeans that can feel constricting, wide leg styles offer a sophisticated silhouette that balances proportion beautifully with oversized knits or tailored blazers.
Opt for high-waisted versions in rich fabrics like wool blends or thick denim to create an elongated effect that flatters all body types while providing warmth during colder months.
Accessorizing wide leg jeans elevates the ensemble even further; consider pairing them with a sleek turtleneck and statement coat for a look that’s both refined and effortlessly stylish.
Footwear is crucial—ankle boots, pointed-toe heels, or chic loafers strike the right chord of classic charm.
Add Animal Print Pieces
Animal print pieces are a timeless choice that can elevate the sophistication of any old money winter outfit.
When thoughtfully incorporated, these prints exude confidence and individuality without veering into bold territory.
Imagine a well-tailored camel coat, elegantly draping over an understated ensemble, complemented by rich leopard print shoes or a subtly embossed snake skin handbag.
The key is to select accessories that offer just a hint of wild elegance while remaining in harmony with the overall palette.
Moreover, layering becomes an art form with animal prints—they are perfect for adding texture and depth to winter outfits.
A soft cashmere turtleneck paired with a tailored midi skirt can be effortlessly enhanced by slipping on knee-high boots featuring a delicate crocodile pattern.
This juxtaposition not only modernizes classic silhouettes but also breathes new life into traditional aesthetics.
Wear a Stylish Winter Hat
@nlmarilyn
A stylish winter hat is not just a practical accessory but a transformative piece that can elevate any outfit to new heights of chic sophistication.
Think beyond the staple beanie and into the realm of fur hats or cashmere berets.
These classic styles evoke an air of refinement reminiscent of vintage European street fashion, making them perfect companions for your old money winter wardrobe.
Pairing a structured hat with tailored outerwear creates an effortlessly luxurious look that whispers sophistication while keeping you warm.
This post was all about old money winter outfits.
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