When it comes to winter fashion, the concept of “old money” style exudes timeless sophistication and understated luxury. If you’re someone who appreciates classic fashion and wants to dress like you’ve inherited wealth without looking flashy, the winter months offer the perfect opportunity to show off your refined style. Lets explore 21 Best Winter Old Money Outfits for Men
Old money style is all about looking polished and confident without drawing too much attention to your outfit. So, whether you’re headed to an elegant winter gala, a business meeting, or just out for a casual stroll, these outfits will help you channel that sophisticated vibe while staying cozy in the cold weather.
Celebrity-Inspired Winter Old Money Outfits for Men
When it comes to casual elegance, few combinations are as effortlessly stylish as an old money-inspired jacket paired with well-tailored jeans. The jacket should feature high-end fabrics like wool or cashmere—think Burberry or Ralph Lauren. Pair this with premium Nike shoes to add a modern twist, maintaining the balance between luxury and practicality. The jeans should be fitted but comfortable, offering a sharp silhouette without being too tight.
This look embodies the essence of old money with a contemporary twist, making it perfect for a winter day out in the city.
21 Best Winter Old Money Outfits for Men
Old Money Style Sleeveless Sweater with Straight Jeans
The sleeveless sweater is a versatile piece that can easily be incorporated into any wardrobe. Opt for neutral tones like navy, beige, or classic grey. Brands like Loro Piana and Brunello Cucinelli offer high-quality options that will make you feel like you’re wearing the best of luxury. Pair this with straight-leg jeans for a polished yet laid-back look. A pair of sleek loafers or Chelsea boots completes this outfit with effortless style.
White Shirt Over Sweater Set with Long Pants
Layering is key when it comes to winter fashion, and the white shirt over a sweater set with long pants is a classic example of how to master the art of layering without overcomplicating things. The white shirt should be crisp and tailored, and the sweater set should be knit from a high-quality fabric like cashmere. Go for well-fitted trousers in a neutral shade, ensuring they drape well without bunching at the ankles.
Button-Down Shirt with Old Money Style Cargo Pants
Cargo pants have evolved from their utilitarian roots into a fashionable and versatile piece, especially when paired with a crisp button-down shirt. Opt for a traditional button-down in a light shade like white, blue, or even subtle stripes. The cargo pants should be slim-fit, ideally in a wool blend or a high-quality cotton fabric. Brands like Brioni or J.Crew have made it possible to wear cargo pants in a more refined way, giving this outfit an elegant edge.
Knitted Sweater with White Jeans and Ankle Boots
A knitted sweater is the quintessential winter piece, and pairing it with white jeans creates a high-contrast look that screams sophistication. Opt for a soft, chunky knit sweater from brands like Gucci or The Row and match it with tailored white jeans. Finish the look with a pair of stylish ankle boots to add warmth and edge to the outfit.
Knitted Collar Sweater with High-Waist Trousers
A knighted collar sweater is an elevated take on the traditional crew neck or V-neck sweater. Its structured collar adds a touch of class, perfect for pairing with high-waist trousers. Ermenegildo Zegna offers premium options that blend Italian craftsmanship with modern style. High-waist trousers in wool or flannel keep you cozy while remaining chic. This outfit is ideal for a day at the office or a lunch with friends.
White Shirt Over Sweater with Jeans
For a more casual take on the old money aesthetic, pairing a white shirt over a sweater with jeans is an easy yet sophisticated option. Go for a slim-cut sweater in cashmere, and opt for a classic button-down shirt underneath. Slim-fit jeans in dark denim will ensure that your look stays polished without being too formal.
Old Money Style Shirt with White Trousers and Loafers
This old money look features a crisp, well-tailored shirt in a solid color—think white, light blue, or even pale pink. Pair it with a set of white trousers for a refined and classy look. Loafers are the footwear of choice for this ensemble, adding a touch of elegance that exudes wealth without being overt. This look is perfect for a more formal occasion or even a day at work.
Old Money Style Cargo Pants with White Shirt
For an easygoing yet classy look, old money style cargo pants can be paired with a crisp white shirt. Look for cargo pants with a slim fit and high-quality fabric—opt for wool or a cotton-blend that keeps you warm but still looks refined. The white shirt should be neatly pressed, preferably in a lightweight cotton fabric that breathes well for those colder months.
Sweat Shirt with Trouser and Nike Shoes
For an updated take on old money style, consider pairing a sweater shirt with formal trousers and premium Nike shoes. The sweater shirt should be fitted and ideally made of soft merino wool or a similar fabric that offers both comfort and style. When paired with tailored trousers, this combination strikes the perfect balance between casual and business casual. The Nike shoes add a modern and athletic twist to the old money aesthetic.
Open Shirt with Trouser
The open shirt with trousers look is simple yet incredibly refined. A button-down shirt in a soft cotton fabric can be worn open, either over a t-shirt or directly on its own. Pair this with a tailored pair of trousers—preferably in wool or a wool-blend fabric for winter—and finish off the look with sleek dress shoes or loafers.
Collared Sweater Shirt with Formal Trouser
If you want to embrace the classic preppy vibe, the collared sweater shirt with formal trousers is a fantastic option. This style is perfect for formal occasions or business settings. A collared sweater shirt offers a bit more structure and formality compared to a standard crew neck, and pairing it with tailored trousers will give you a sharp, elegant look.
Skinny Fit Sweater Set with White Trouser and Nike Shoes
This outfit combines comfort and elegance. The skinny fit sweater set will give you a sleek, modern silhouette while maintaining a sophisticated look. Pair it with white trousers for a sharp contrast and finish the outfit with a pair of sleek Nike shoes for a subtle nod to street style.
Check Shirt with High-Waist Jeans
The check shirt with high-waist jeans combination is perfect for anyone who wants to add a little pattern into their wardrobe without being too bold. The high-waist jeans provide structure and elongate the legs, while the check shirt adds texture and interest to the outfit. Tuck in the shirt for a more refined look, and add loafers or boots to complete the ensemble.
Read More:- How to Style Sweater in Winter for Men: 21 Best Stylish Outfit Ideas to Keep You Warm
Skinny Fit Collared Shirt with White Formal Trouser
A skinny-fit collared shirt paired with white formal trousers is the ideal look for a business meeting or a formal event. The skinny fit ensures that the outfit remains sleek and sharp, while the collared shirt keeps things formal. White formal trousers are a versatile piece that can be dressed up or down depending on the occasion.
Sleeveless Knitted Sweater with Formal White Trouser
For a more sophisticated and streamlined look, the sleeveless knitted sweater paired with formal white trousers is a timeless option. Choose a soft, high-quality sweater in a neutral color to keep things classic and elegant. Pair it with crisp white trousers that fit well and are tailored to perfection.
All Black with Old Money Style Shawl
An all-black outfit exudes a certain sophistication that can never go wrong. Pair black trousers, a black sweater, and an old money style shawl for a look that’s both cozy and refined. This outfit is perfect for winter nights out or even a casual office day.
Zip Sweater with Formal Trouser and Sneakers
For a modern take on the old money style, a zip sweater paired with formal trousers and sneakers is a fantastic choice. The zip sweater adds a bit of flair, while the sneakers keep the outfit casual yet stylish. This combination works well for both business casual settings and weekend outings.
Button-Down Shirt with Trouser
A simple but timeless combination, the button-down shirt with trousers is perfect for a more formal look. Opt for high-quality fabric, such as Egyptian cotton for the shirt, and wool-blend trousers. Finish off with loafers for a polished appearance.
Premium Quality White Sweater Shirt with Formal Trouser and Nike Shoes
For a refined yet relaxed look, a premium white sweater shirt paired with formal trousers and Nike shoes is an excellent choice. The sweater shirt is a great alternative to a button-down shirt, offering more warmth and texture during the winter months.
Celebrity-Inspired Jacket with Black Jeans and Premium Nike Shoes
If you want to add a little flair to your old money style, a celebrity-inspired jacket paired with black jeans and premium Nike shoes will take your winter wardrobe to the next level. Look for jackets in luxurious fabrics like wool or leather, and pair them with dark, tailored jeans and sleek sneakers.
FAQs About Old Money Style for Men
What is old money style for men?
Old money style for men is all about understated luxury, classic pieces, and timeless tailoring. Think muted tones, high-quality fabrics, and a polished, refined look without ostentatious logos or flashy items.
How do I dress old money without looking outdated?
To achieve a modern old money look, incorporate contemporary pieces like premium sneakers or tailored jeans with timeless fabrics like wool, cashmere, and linen. Keep accessories subtle and avoid anything too trendy.
Can I wear sneakers with old money style outfits?
Absolutely! Sneakers can be a great addition to an old money style look, as long as they are sleek and high-quality, like Nike or Common Projects. Pair them with well-tailored trousers or a classic blazer to maintain the refined vibe.
Where can I buy old money style clothing?
Look for brands known for their timeless style, like Ralph Lauren, Brioni, Loro Piana, and Burberry. These brands often offer pieces that are both sophisticated and practical for winter.
Is layering important in old money style for winter?
Yes, layering is essential in old money style, especially during winter. Opt for classic layering pieces like wool coats, cashmere sweaters, and scarves that not only add warmth but elevate your overall appearance.
Tips for Nailing Old Money Style in Winter
Focus on quality: Invest in high-quality fabrics like wool, cashmere, and flannel to ensure your outfits look polished and refined.
Neutral tones: Stick to neutral colors like beige, navy, and grey for a sophisticated, timeless look.
Tailoring is key: Make sure your clothes are well-tailored for
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