Classy Old Money Winter Outfits for Women | 16 Chic & Elegant Looks

Winter is the perfect time to embrace timeless elegance while staying warm and stylish. For women who love the classy “old money” aesthetic, winter dressing is all about quality fabrics, polished silhouettes, and subtle sophistication.

In this guide, we’ve curated 16 stunning winter outfit ideas that balance comfort with luxury, making it easy to look effortlessly chic whether you’re heading to the office, a winter brunch, or a casual gathering. From tailored wool coats and ribbed knit sets to mock neck sweater dresses, each outfit has been carefully selected to inspire refined, age-appropriate, and classy winter looks. Read on to discover how you can elevate your winter wardrobe with these timeless pieces.

16 Classy Old Money Winter Outfit Ideas for Women

1. Winter birthday outfits for women

This elegant 2-piece sweater dress set is a perfect choice for women looking for classy winter outfits to wear on their birthday. Featuring a ribbed knit crop sweater paired with a flattering bodycon midi tank dress, this outfit blends warmth, sophistication, and modern style. The long sleeves and cozy knit fabric make it ideal for winter celebrations, while the fitted silhouette adds a polished and feminine touch. Whether styled with boots or heels, this look stands out as a classy winter birthday outfit for women that feels chic, comfortable, and effortlessly stylish.

2. Winter Long Skirt Outfit with Chunky Cable Knit Set

This classy long skirt outfit for winter features a chunky cable knit two-piece set that blends cozy texture with timeless elegance. The flowing long knit skirt creates a graceful silhouette, while the matching sweater adds warmth without sacrificing style. Ideal for refined winter outings, casual formal settings, or elegant daytime looks, this outfit pairs beautifully with ankle boots or heeled boots, a tailored coat, and minimal accessories. The result is a polished, feminine winter ensemble that feels both comfortable and effortlessly sophisticated.

Camel Double-Breasted Coat for Elegant Winter Travel

This camel wool-blend mid-long coat is a timeless staple for women planning a stylish winter trip. The double-breasted design and notch lapel add a refined, structured feel, while the longer length offers extra warmth during chilly travel days. Its neutral camel tone makes it incredibly versatile—easy to style with jeans, knit dresses, boots, or scarves—so you can create multiple winter trip outfits with one outerwear piece. Whether you’re exploring a new city or heading out for a cozy dinner, this coat delivers comfort, warmth, and effortless elegance throughout your journey.

3. Chic Winter Outfits – Elegant 2-Piece Knit Wide-Leg Sweater Set

This stylish 2-piece knit sweater set is a beautiful example of chic winter outfits classy, combining comfort with modern elegance. Designed with a flattering V-neck sweater and wide-leg knit pants, this outfit creates a relaxed yet polished winter look. The soft knit fabric keeps you warm while maintaining a sleek silhouette, making it perfect for casual outings, brunch dates, or cozy winter gatherings. When styled with ankle boots or a long coat, this set transforms into a chic and classy winter outfit that feels effortlessly sophisticated.

4. Elegant Winter Outfits – Long Sleeve A-Line Knit Midi Sweater Dress

This long-sleeve A-line knit midi sweater dress is a timeless choice for elegant winter outfits classy, offering a refined silhouette that feels both sophisticated and season-appropriate. The soft knit fabric provides warmth without sacrificing style, while the midi length and flattering A-line cut create an effortlessly polished look. Ideal for winter weddings, cocktail events, or formal gatherings, this dress delivers elegance, comfort, and classic charm in one beautifully designed winter outfit.

5. New York Winter Outfit with Tailored Shacket Set

This New York aesthetic winter outfit blends relaxed tailoring with effortless city elegance. Featuring a button-down shacket jacket and matching long sweatpants, this two-piece set captures the signature NYC balance of comfort and sophistication. The structured shacket elevates the look, while the streamlined pants keep it polished and wearable for everyday winter city life. Style it with ankle boots or loafers, a wool coat, and minimal accessories to achieve a chic, street-smart winter outfit inspired by classic New York fashion.

6. Winter Outfits Black Women – Chic 2-Piece Knit Cardigan & Maxi Dress Set

This stylish 2-piece knit set is a beautiful example of classy winter outfits Black women, offering both comfort and refined elegance for the colder season. Featuring a long-sleeve cropped cardigan paired with a sleek maxi dress, this outfit creates a flattering, elongated silhouette that complements natural curves. The soft knit fabric provides warmth, while the coordinated design delivers a polished and sophisticated winter look. Perfect for casual outings, dinner dates, or special occasions, this set blends modern style with timeless class.

7. Winter Date Night Outfit – Off-Shoulder Bodycon Sweater Dress

This elegant winter outfit is perfect for a romantic date night or dinner. The off-shoulder bodycon sweater dress combines warmth with sophistication, featuring long sleeves and a midi-length silhouette that keeps the look classy and refined. The soft knit fabric hugs curves subtly while maintaining comfort, making it ideal for a winter evening outing. Pair with heeled boots, a statement clutch, and delicate jewelry to create a polished, romantic ensemble that exudes confidence and winter elegance.

8. Hijabi Winter Outfits – Elegant Long Sleeve Abaya Kaftan Dress

This long sleeve abaya kaftan dress is a beautiful choice for hijabi winter outfits classy, offering modest coverage with an elegant, refined design. Crafted in a flowing silhouette, it provides comfort and warmth while maintaining a graceful, polished appearance. The pure color design and loose fit make it easy to layer with coats or cardigans during winter, while the khimar-style look adds a timeless and sophisticated touch. Ideal for prayers, gatherings, or everyday wear, this outfit blends modest fashion with classy winter elegance.

9. Professional Winter Outfit with Camel Wool Double-Breasted Coat

This professional winter outfit for women is centered around a camel wool-blend double-breasted coat, a timeless piece for polished cold-weather dressing. The tailored mid-long length and structured notch lapel create a refined, office-ready silhouette that works effortlessly over work dresses, tailored trousers, or matching suits. The neutral camel shade adds understated elegance, making this outfit ideal for corporate settings, business meetings, and professional winter commutes. Complete the look with heeled ankle boots, a structured tote, and minimal accessories for a confident, sophisticated winter ensemble.

10. Formal Outfit with Tailored Wool Peacoat

This outfit for women is built around a tailored wool peacoat, making it a perfect choice for polished cold-weather dressing. The structured silhouette and notch lapel instantly elevate the look, creating a refined and professional appearance suitable for office wear or formal winter occasions. Styled with tailored trousers or a sleek midi dress, this outfit balances warmth with elegance. Finish the look with pointed-toe boots, a structured handbag, and minimal jewelry for a timeless, sophisticated winter ensemble.

11. Black Winter Outfit with Ribbed Knit Midi Dress Set

This black winter outfit features a ribbed knit two-piece set with a fitted bodycon midi dress and a matching long-sleeve cropped sweater, creating a sleek and elegant cold-weather look. The all-black palette adds timeless sophistication, while the structured ribbed texture enhances the outfit’s polished appeal. Perfect for winter dinners, evening outings, or elevated casual occasions, this look pairs beautifully with knee-high boots, a tailored wool coat, and minimal gold accessories for a refined, effortlessly chic winter style.

12. Luxury Winter Outfit with Knit Co-Ord and Wide-Leg Pants

This luxury winter outfit embraces understated elegance with a matching knit co-ord set featuring a long-sleeve pullover and wide-leg pants. The fluid silhouette and soft knit texture create a refined, high-end look that feels both modern and effortless. Perfect for classy winter outings, travel days, or elevated casual occasions, this outfit pairs beautifully with a tailored wool coat, sleek boots, and a structured handbag. The result is a polished winter ensemble that captures minimalist luxury while prioritizing comfort and sophistication.

13. Winter Pencil Skirt Outfit with Wool Plaid Mini Skirt

This classy winter pencil skirt outfit features a high-waisted wool plaid pencil skirt that brings structure and sophistication to cold-weather dressing. The fitted silhouette creates a polished, feminine shape, while the wool fabric adds warmth and seasonal elegance. Perfect for office wear, smart casual events, or refined winter outings, this look pairs effortlessly with a fitted knit sweater or crisp blouse, opaque tights, and knee-high boots. Finished with a tailored coat and minimal accessories, it’s a timeless winter outfit that feels both chic and confidently classy.

14. Winter Outfit for Women Over 50

This classy winter outfit for women over 50 features a turtleneck oversized sweater tunic with long batwing sleeves and a chic split hem, blending comfort with timeless elegance. The soft knit fabric and relaxed fit provide warmth while maintaining a polished silhouette, making it ideal for mature styling. Pair it with tailored trousers, sleek ankle boots, or even a long-line coat for a sophisticated winter look that is both flattering and effortlessly stylish. Perfect for casual gatherings, winter strolls, or refined everyday wear, this sweater tunic proves that winter fashion can be cozy and classy at any age.

15. Boho Outfit with Turtleneck Ribbed Sweater

This outfit features a turtleneck ribbed sweater that perfectly blends cozy warmth with chic sophistication. The fitted knit design enhances your silhouette, while the textured ribbing adds a subtle bohemian flair. Ideal for layering over flowy skirts, wide-leg pants, or pairing with statement belts and boots, this sweater creates a refined yet relaxed winter look. Perfect for casual winter outings, cozy gatherings, or stylish everyday wear, it’s a versatile piece that effortlessly captures the boho-classy vibe.

16. Old Money Winter Outfit

This classy winter outfit embodies the old money aesthetic with a mock neck ribbed sweater mini dress that balances elegance and modern style. The fitted bodycon silhouette adds refinement, while the soft ribbed knit ensures warmth and comfort for winter months. Pair it with a tailored wool coat, knee-high leather boots, and a structured handbag for a polished, sophisticated look. Ideal for winter gatherings, brunches, or elegant casual occasions, this outfit exudes effortless luxury, proving that timeless style is the ultimate statement.