Baby, it’s cold outside, but your footwear doesn’t have to be a fashion faux pas. Forget those bulky, unflattering winter boots. This season, elevate your style with boots that offer both warmth and a sophisticated edge. We’ve curated a guide featuring top men’s boot styles, with insights from fashion expert Marisa Meloski of Stilista|Boston, to help you navigate the winter months in impeccable style.
Tobias Shearling-Lined Leather Boot, Overland Sheepskin Co.
Price: $299
Style Statement: The Tobias Shearling-Lined Leather Boot from Overland Sheepskin Co. offers a harmonious blend of ruggedness and refinement. The full shearling lining promises exceptional warmth and comfort, while the graphite nubuck leather provides a stylish alternative to the ubiquitous black and brown winter boots, standing out subtly without being overly loud. Its sleek profile, despite the robust lug sole, makes it a versatile choice for various occasions.
Stylist’s Take: Marisa Meloski suggests embracing the boot’s inherent versatility. For a classic workwear-inspired look, pair these graphite boots with denim or duck canvas. To elevate your style, consider corduroy or flannel trousers. A crewneck sweater complements the workwear vibe, while a turtleneck, shawl collar pullover, or cardigan adds a touch of sophistication. Marisa emphasizes coordinating your sweater with the gray tones of the boots or creating a tonal ensemble by pairing them with gray trousers for a cohesive and fashionable winter outfit.
Fashion Verdict: The Tobias boot is a dependable and stylish choice for everyday men’s fashion. Its versatility makes it ideal for navigating winter weather while maintaining a sharp look.
Brixen, Koio
Price: $395
Style Statement: Koio’s Brixen boot, handcrafted in Italy, merges high-fashion aesthetics with outdoor functionality. Featuring a shearling lining and Koio’s ArcticLug outsole, the Brixen embodies a hiking-inspired design that’s equally at home in urban snowscapes or upscale ski resorts. These boots are designed for the fashion-conscious man who demands both style and performance in his winter footwear.
Stylist’s Take: Marisa highlights the authentic hiking boot aesthetic of the Brixen, accentuated by speed hooks and round laces. She recommends pairing these boots with straight-leg pants in a regular or classic fit, allowing the pant leg to drape naturally over the boot shaft. A Fair Isle sweater adds a timeless touch to the ensemble, enhancing the winter fashion appeal. For an extra layer of style, Marisa suggests a shearling jacket in a flight or biker style, completing a rugged yet fashionable look.
Fashion Verdict: The Koio Brixen boots are a stylish investment for men seeking fashionable yet functional winter footwear. Their Italian craftsmanship and versatile design make them a standout choice for the style-conscious man.
Ranger II Hiking Boot, Lucchese Bootmaker
Price: $425
Style Statement: Lucchese Bootmaker’s Ranger II Hiking Boot boasts a traction outsole and exquisite leather craftsmanship, making it suitable for both outdoor adventures and sophisticated urban settings. While designed for performance, the Ranger II’s luxurious leather elevates it beyond typical hiking boots, offering a refined option for men who appreciate high-quality materials and versatile style in their boot fashion.
Stylist’s Take: Marisa emphasizes the Ranger II’s impressive fashion adaptability. For a relaxed weekend style, she suggests pairing them with denim, a reverse weave sweatshirt, a ball cap, and a camel overcoat. For a business casual office environment, chinos, a classic blue oxford shirt, a chocolate-toned belt, and a wool herringbone blazer create a polished yet approachable look. The Ranger II boots seamlessly bridge the gap between rugged and refined in men’s fashion.
Fashion Verdict: The Lucchese Ranger II boots are a premium choice for men seeking fashionable boots that can transition effortlessly from outdoor activities to smart casual settings. Their versatility and elegant design make them a valuable addition to a stylish wardrobe.
Northbound 6” Waterproof Insulated Lace Up, Chippewa
Price: $180
Style Statement: Chippewa’s Northbound 6” Waterproof Insulated Lace Up boots combine work boot practicality with street-style appeal. The wheat nubuck leather provides a fashionable edge, while the waterproof construction ensures functionality in winter conditions. These boots are ideal for men who need reliable weather protection without sacrificing style in their everyday boot fashion choices.
Stylist’s Take: Marisa advises leaning into the workwear aesthetic of the Northbound boots. She recommends pairing them with mid-tone blue selvedge denim, a long-sleeve thermal Henley, a heavy canvas or flannel-lined chore coat, and a wool beanie. This combination embraces the boot’s rugged nature while creating a cohesive and stylish workwear-inspired men’s fashion ensemble.
Fashion Verdict: Chippewa Northbound boots offer a practical yet fashionable option for men seeking durable, waterproof winter boots with a workwear edge. They are a solid choice for those who value both function and style in their boot selection.
Shearling Boot, Toscana USA
Price: $678
Style Statement: The Shearling Boot from Toscana USA epitomizes luxury in men’s boot fashion. Detailed with buffalo calf upper, ostrich padded collar, and crocodile skin accents, these Italian-made boots exude opulence. The patented dip-dye process ensures supple leather and immediate comfort, while the Vibram lug sole adds practicality without compromising the boot’s lightweight feel.
Stylist’s Take: Marisa describes these Toscana boots as “gorgeous” and envisions them styled for a sophisticated, tailored look. She suggests pairing them with dark denim, a dress belt, a fitted merino wool or cashmere polo sweater, and a sport coat in a rich, textured fabric. The ensemble should be slim-fit, sleek, and impeccably tailored, complemented by a navy dress coat and a richly colored scarf for a truly high-fashion statement.
Fashion Verdict: Toscana Shearling Boots are a statement piece for men who demand the highest level of luxury and style in their winter boot fashion. They are an investment in unparalleled craftsmanship and sophisticated design.
Shasta Boot Tall, UGG
Price: $500
Style Statement: UGG’s Shasta Boot Tall is a maximalist statement in men’s winter boot fashion. Reaching mid-calf and lined with UGGplush insulation, these boots are engineered for extreme cold and designed for bold style. They are the ultimate choice for men with a strong street-style aesthetic who want their footwear to be both a performance piece and a head-turning fashion statement.
Stylist’s Take: Marisa acknowledges the Shasta Boot Tall’s striking design but cautions that it’s not for everyday wear or the style masses. She suggests it might be appropriate for après-ski in Aspen but warns against potential ’90s hip-hop video extra comparisons in more ordinary settings. The Shasta boot is for a specific, daring fashion sensibility.
Fashion Verdict: UGG Shasta Boot Tall is for the fashion-forward man who wants to make a bold statement with his winter footwear. While not for everyone, these boots guarantee warmth and attention, appealing to a niche within men’s boots fashion.
