Winter Sales 2026: 15 Old Money Men's Items to Buy
January brings with it that rare window of opportunity when quality becomes more accessible. The 2026 winter sales aren't an invitation to hoard, but an opportunity for those who recognize value.
Those who follow the Old Money philosophy know the difference between buying and investing. A 50% merino wool sweater isn't just a bargain: it's a piece that will last through the winters with the same elegance it brings to your wardrobe today. The 2026 men's winter sales represent precisely this opportunity.
We've selected 15 pieces from our collection, each on sale and each capable of building, not filling, your wardrobe. No impulse purchases, just thoughtful choices for those who prefer to own less, but better.
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How we selected these 15 items
Not all items on sale are worth your while. Our selection for the 2026 winter sales follows three precise criteria: quality materials , versatility in combinations , and verifiable real discounts .
Each piece you'll find in this guide answers a simple question: will it still be in your closet in five years? If the answer is uncertain, it doesn't belong on this list. We've favored natural fabrics like merino wool, cotton, and suede; classic colors like navy, gray, camel, and beige; and cuts that don't follow passing fads.
"Buy less, choose better, make it last." — Vivienne Westwood
💡 Old Money Tip: Before the sales, take a photo of your closet. Identify what's actually missing, not what looks attractive in the window display. Elegance is built by filling gaps, not by accumulating duplicates.
Knitwear: The sweaters you can't miss
Knitwear is the heart of your winter wardrobe. A quality sweater isn't just a warm garment: it's an investment that, if cared for carefully, will last a lifetime. Here are the five pieces we think deserve special attention during the 2026 men's winter sales.
Merino Wool Zip Sweater
The Merino Wool Zip Sweater embodies the perfect balance between elegance and practicality. The half-zip allows you to regulate your temperature without compromising style, while the merino wool ensures softness and breathability. It's the kind of piece you wear under a blazer for a business lunch or alone for a Sunday stroll.
€99.00 €198.90 — 50% off
Turtleneck Sweater
The turtleneck is a timeless classic. Our Turtleneck Sweater offers a clean silhouette that's suitable for both formal and casual settings. Available in neutral shades, it's the piece Marcello Mastroianni would have chosen for an afternoon in Rome.
€46.50 €69.00 — 33% off
Men's Merino Wool Sweater
For those seeking a more traditional fit, the Men's Merino Wool Sweater offers uncompromising comfort and style. Merino wool retains warmth without weighing you down, ideal for those who move between heated interiors and cold exteriors.
€54.90 €84.90 — 35% off
Half Zip Sweater
The Half-Zip Sweater is a more accessible option without sacrificing style. Versatile and comfortable, it pairs easily with gray trousers or beige chinos.
€34.99 €54.00 — 35% off
Men's Cardigan Sweater
A cardigan discreetly completes any outfit. Our men's button-up cardigan sweater offers the versatility to suit both the office and leisure. It can be worn open over a shirt or closed as an alternative to a classic sweater.
€54.90 €65.90 — 17% off
🛍️ Shop the Look: Knitwear
- Merino Wool Zip-Up Sweater — €99.00 €198.90
- Turtleneck Sweater — €46.50 €69.00
- Men's Merino Wool Sweater — €54.90 €84.90
- Half-Zip Sweater — €34.99 €54.00
- Men's Cardigan Sweater — €54.90 €65.90
Outerwear: jackets for winter
A quality outerwear piece is perhaps the most visible investment you can make in your wardrobe. It's the first thing others notice, the one that defines the first impression. During the 2026 winter sales, two jackets deserve special attention.
Men's Winter Jacket
The Men's Winter Jacket perfectly combines functionality and style. Warm without being bulky, elegant without being stuffy: it's the kind of jacket you can wear from November to March without ever feeling out of place. At 50% off, it's a rare option for those seeking versatile outerwear.
€99.99 €200.00 — 50% off
Faux Suede Jacket
For transitional seasons or milder winter days, the Faux Suede Jacket offers a refined alternative. The suede texture adds depth to outfits without being overbearing, perfect for those looking for something different from the usual jacket.
€54.90 €70.00 — 22% off
🛍️ Shop the Look: Outerwear
- Men's Winter Jacket — €99.99 €200.00
- Faux Suede Jacket — €54.90 €70.00
Elegant trousers and suits
Pants are the foundation of any outfit. A well-cut pair of elegant trousers can elevate even the simplest sweater, while a poorly chosen pair can ruin the most refined jacket. Here are our picks for the 2026 men's winter sales.
Men's Elegant Trousers
Men's elegant trousers embody the essence of understated style: clean lines, quality fabric, and an impeccable fit. They pair effortlessly with sweaters, shirts, and blazers.
€34.90 €50.00 — 30% off
Ceremony Dress
A formal dress is the ultimate investment. A quality dress isn't bought for a specific occasion: it's purchased knowing it will be perfect for weddings, baptisms, and all those occasions where elegance isn't optional. For more on combinations, consult our guide to winter formal outfits .
€130.00 €260.00 — 50% off
Slim Fit Cotton Shirt
No wardrobe is complete without quality shirts. The SlimFit Cotton Shirt offers a contemporary cut and premium fabric. It's the kind of shirt that stands out for its fit, not for its flashy details.
€44.90 €79.90 — 44% off
🛍️ Shop the Look: Pants and Suits
- Men's Elegant Trousers — €34.90 €50.00
- Formal Dress — €130.00 €260.00
- Slim Fit Cotton Shirt — €44.90 €79.90
Footwear: moccasins and suede shoes
Shoes say a lot about the wearer. In the world of classic style, footwear is never flashy, but always impeccable. For those who want to learn more about how to style these styles during the cold season, we recommend our guide on how to wear loafers in winter .
Suede Driving Shoes Moccasins
Suede Driving Shoes are a timeless classic. The suede lends a discreet elegance, while the flexible sole ensures all-day comfort. They're the kind of shoe you only notice when it's missing. At 51% off, they're the most attractive offering in this selection.
€89.90 €185.00 — 51% off
Men's Suede Shoes
For those seeking a more structured alternative, men's suede shoes offer versatility and style. They pair equally well with dress pants and dark jeans. To keep them looking impeccable over time, check out our guide on how to clean suede shoes .
€69.90 €99.90 — 30% off
🛍️ Shop the Look: Footwear
- Suede Driving Shoes Moccasins — €89.90 €185.00
- Men's Suede Shoes — €69.90 €99.90
Summary table: all 15 items compared
To make your choice easier, here are all the items selected for the 2026 winter sales, sorted by percentage reduction.
| Boss | Category | Price | Reduction |
|---|---|---|---|
| Suede Driving Shoes Moccasins | Footwear | €89.90 | 51% |
| Merino Wool Zip Sweater | Knitwear | €99.00 | 50% |
| Ceremony Dress | Complete | €130.00 | 50% |
| Men's Winter Jacket | Outerwear | €99.99 | 50% |
| Slim Fit Cotton Shirt | Shirts | €44.90 | 44% |
| Men's Merino Wool Sweater | Knitwear | €54.90 | 35% |
| Half Zip Sweater | Knitwear | €34.99 | 35% |
| Turtleneck Sweater | Knitwear | €46.50 | 33% |
| Men's Elegant Trousers | Pants | €34.90 | 30% |
| Men's Suede Shoes | Footwear | €69.90 | 30% |
| Faux Suede Leather Jacket | Outerwear | €54.90 | 22% |
| Men's Cardigan Sweater | Knitwear | €54.90 | 17% |
Frequently Asked Questions about the 2026 Winter Sales
When do the 2026 winter sales start in Italy?
The 2026 winter sales begin on Saturday, January 4th in most Italian regions. They generally last 60 days, with possible regional variations. Some regions, such as Sicily and Valle d'Aosta, may have slightly different dates.
What's best to buy in the men's winter sales?
The best pieces to buy are timeless ones: wool or cashmere sweaters, quality jackets, classic trousers, and leather or suede shoes. Avoid items that are too tied to seasonal trends, which risk looking dated next year.
How to recognize a real discount from a fake one?
Check the original price on official websites before the sales begin. A reputable brand maintains consistent prices throughout the year. Be wary of discounts exceeding 70% on supposedly high-quality items: they often hide artificially inflated margins.
Which colors should you choose for a versatile wardrobe?
The most versatile colors are navy, all shades of gray, beige, camel, and white. These shades combine effortlessly and allow you to create dozens of different combinations with just a few pieces. Black, while elegant, is often less versatile than you might think.
How long do the 2026 winter sales last?
The standard duration is 60 days from the start date, so until early March 2026. However, the best items tend to sell out within the first two weeks. Those looking for specific pieces should not wait too long.
How to care for wool items purchased on sale?
Wool requires care: hand wash or delicate cycle at low temperatures, dry flat to avoid warping, and store with natural moth repellants like lavender or cedar. A well-cared for sweater can last for decades, maintaining its beauty intact.
🎯 Build your wardrobe
The 2026 winter sales represent an opportunity for those who choose quality. Our selection is designed to build, not fill, your wardrobe.
"Quality is remembered long after the price has been forgotten." — Aldo Gucci
Conclusion
The 2026 men's winter sale offers a real opportunity for those looking to build a quality wardrobe. The 12 pieces we've selected—from merino wool sweaters to versatile jackets, from classic trousers to suede shoes—represent the best of our collection, all sharing the same philosophy: less, but better.
A smart purchase during the sales isn't about saving the most, but about what you'll use the most. Choose carefully, invest in quality, and your wardrobe will thank you for years to come.