Winter. It’s the season of crisp air, cozy evenings, and, for the discerning man, a prime opportunity to redefine your style. While summer’s fashion landscape can feel stripped down, winter offers a canvas for layering, texture, and thoughtful silhouette. It’s a time when embracing new trends isn’t just about looking good, but about feeling confident and comfortable in your own skin, no matter the weather.
This season, the trends are leaning into familiar, yet refined, territory. Think elevated sportswear, a modern take on preppy classics, a nod to the cool confidence of the ’90s, and the practical durability of outdoor gear. These aren’t fleeting fads; they’re adaptable styles that blend seamlessly into your existing wardrobe, offering versatility and a fresh perspective. To help you navigate these trends, we’ve consulted with menswear expert and stylist Ted Stafford, who champions timeless pieces with modern relevance.
Let’s dive into the key winter trends that every man should consider incorporating into his rotation.
Sportscenter: Retro Athletic, Replayed
This trend is all about recapturing the spirit of vintage sports apparel, but with a polished finish that transitions effortlessly from a casual coffee run to an evening out. Forget the ill-fitting sweats of yesteryear; this is about smart, athletic-inspired silhouettes designed for modern life.
Key Elements:
- Silhouettes: Look for track jackets with clean lines, snap-front pants that offer a relaxed yet put-together vibe, and raglan-sleeve baseball tees. These pieces provide comfort without sacrificing a sharp appearance.
- Color Palette: Earthy tones are your best friend here. Browns, burnt oranges, mustard yellows, forest greens, and creamy off-whites lend a sophisticated and warmer feel to sporty garments. This palette feels grounded and versatile.
- Footwear: The right sneakers are crucial. Opt for retro styles, particularly those with slim, streamlined silhouettes. They have the power to instantly elevate a simple outfit, transforming a basic jeans-and-tee combo or a tracksuit into a style statement.
Practical Workout Tip:
Embrace the athletic aesthetic in your activewear. A well-fitting track jacket can be just as effective for a brisk walk or a light gym session as it is for a casual outing. Pair it with comfortable, moisture-wicking leggings or shorts, and finish the look with your favorite retro sneakers. This dual-purpose approach maximizes your wardrobe’s utility.
Real-Life Example:
Imagine heading to a weekend brunch. You could pair a forest green raglan sleeve t-shirt with dark wash, straight-leg jeans. Layer a classic bomber jacket in a neutral tone over it, and complete the look with a pair of clean, white retro sneakers. This outfit is comfortable, stylish, and nods to the retro athletic trend without being overtly sporty.
Prepped Up: Ivy League, But Practical
The preppy aesthetic is making a strong comeback, but this iteration is less about stuffy formality and more about timeless, versatile pieces that work for your everyday life. It’s about embracing the clean, classic elements of Ivy League style and updating them for a contemporary wardrobe.
Key Elements:
- Foundational Pieces: Invest in high-quality staples like crewneck and cable-knit sweaters, crisp Oxford shirts, durable rugby shirts, and classic cardigans. These items are designed to be layered, providing warmth without bulk.
- Bottoms: Move away from overly slim fits. Corduroy pants and well-fitting chinos are the perfect foundation for this trend. They offer comfort and a touch of texture that complements the classic vibe.
- Footwear: Loafers are the quintessential slip-on shoe for this trend. They effortlessly bridge the gap between casual and smart, looking just as good with jeans and a sweater as they do with chinos and a blazer. Clean leather shoes also fit seamlessly into this aesthetic.
Practical Workout Tip:
Think about how these pieces can enhance your post-workout recovery or casual Fridays. A comfortable cable-knit sweater over a base layer can be incredibly cozy after a chilly outdoor workout. A well-fitting Oxford shirt, perhaps layered under a stylish cardigan, can make for a smart yet relaxed look when you’re heading out for a recovery coffee.
Real-Life Example:
For a smart-casual office day or a dinner date, try pairing navy chinos with a grey cable-knit sweater. Layer a tailored blazer in a complementary shade over the sweater. Finish the look with classic leather loafers. This ensemble embodies the refined preppy style, demonstrating how classic pieces can be updated for modern appeal.
The New ’90s: Relaxed, Not Sloppy
The ’90s revival continues to influence fashion, but this season’s interpretation is about refined relaxation. It’s about embracing looser silhouettes that still maintain a sharp, intentional look. The key is to achieve an effortless cool without looking unkempt.
Key Elements:
- Silhouettes: Straight-leg and relaxed-fit pants are central to this trend. Pair them with easygoing tops like oversized crewneck sweatshirts or vintage-inspired denim shirts. Layering is key, with bomber jackets that sit comfortably on the shoulders adding to the relaxed feel.
- Proportion: The magic of this trend lies in maintaining balance. While pieces are looser, they shouldn’t be baggy. The focus is on proportions that feel intentional and current, ensuring you look put-together rather than sloppy.
- Color Palette: Stick to a neutral and versatile palette. Blacks, navies, grays, olives, and washed denim tones are perfect for this trend. These colors are easy to integrate into your existing wardrobe and lend themselves well to the minimalist aesthetic of the ’90s.
Practical Workout Tip:
Incorporate looser-fitting workout gear that still offers functionality. Think about relaxed-fit joggers or a slightly oversized graphic tee for your gym sessions. The ’90s influence can inspire a more laid-back approach to your activewear, focusing on comfort and a cool, understated style.
Real-Life Example:
A weekend look that nails the ’90s vibe could involve a pair of relaxed-fit dark wash jeans, a simple grey oversized crewneck sweatshirt, and a classic bomber jacket in black or olive. Add a pair of stylish retro sneakers to complete the ensemble. This outfit is comfortable, effortlessly cool, and perfectly captures the essence of the updated ’90s trend.
Country Man: Rugged, Weather-Ready Style
This trend is all about functionality and durability, designed for those who embrace the elements. Even if your "rugged terrain" is just the city sidewalk, this style offers a practical and stylish approach to winter dressing.
Key Elements:
- Layering Essentials: Flannel shirts are a cornerstone, offering warmth and classic style. Pair them with thermal base layers for added insulation. Fleece jackets provide excellent warmth and are perfect for layering.
- Outerwear: Puffer vests offer core warmth without restricting movement, while heavier, durable outerwear pieces are built to withstand the cold. Look for jackets made from robust materials that are designed to last.
- Accessories: These are crucial for completing the rugged look. Consider sturdy field watches, robust leather belts, warm gloves, and cozy beanies. They add both functionality and a touch of masculine charm.
- Footwear: Work boots and hiking-inspired boots are the stars of this trend. They are not only durable and provide excellent grip but also add a substantial, grounded feel to your outfit.
Practical Workout Tip:
This trend is perfect for embracing outdoor winter activities. A durable flannel shirt over a thermal base layer is ideal for hiking or even just a long walk in the park. Invest in a good pair of waterproof boots that can handle various terrains and weather conditions, making them suitable for both your outdoor adventures and everyday wear.
Real-Life Example:
For a casual weekend outing, layer a classic flannel shirt over a thermal tee. Add a fleece jacket or a puffer vest for warmth. Pair with durable, straight-leg jeans and sturdy work boots. Complete the look with a warm beanie and a rugged watch. This outfit is practical, stylish, and ready for whatever the winter weather throws your way.
Embracing Your Personal Style
These winter trends offer a fantastic framework for updating your wardrobe, but the most important element is to adapt them to your personal style and comfort. Don’t feel pressured to adopt every single element of a trend. Instead, pick and choose what resonates with you and how you can best integrate it into your existing wardrobe.
Remember, fashion is a tool for self-expression. Winter’s fashion landscape provides ample opportunity to experiment with textures, layers, and silhouettes. Whether you’re drawn to the athletic appeal of retro sportswear, the timeless charm of preppy classics, the relaxed cool of the ’90s, or the rugged functionality of outdoor gear, there’s a trend to suit every man.
By incorporating these styles thoughtfully, you can not only elevate your winter wardrobe but also boost your confidence and ensure you look and feel your best throughout the season. So, step out with purpose, embrace the change, and make this winter your most stylish one yet.
