The InsideHook Winter Watch Cap Guide

The hat's history, how to wear it and 11 new styles we love

December 12, 2023 2:21 pm
a Missoni beanie on a snowy background
We present the InsideHook guide to beani-erm, watch cap.
Missoni/Getty Images

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It’s safe to say that almost everyone you know owns at least one beanie, or, as I like to call it, a “watch cap.” Like many elements of menswear, the beanie has its roots in the military, and while its exact birthdate remains speculative, the modern “watch cap” owes its name to U.S. sailors who relied on it to stay warm during World War II while standing watch on their ships’ decks.

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This past season, beanies were all over the runway, with luxury brands such as Fendi, Armani, Gucci, and Bode elevating the watch cap to a true luxury accessory.  This transformation from a utilitarian necessity into essential fashion accessory underscores how functional garments often become embedded in our cultural zeitgeist; a reminder that style often thrives on the intersection of form and function.

How you wear a beanie or watch cap says a lot about your personal style. These days, it’s not just about keeping warm; it’s also a statement. I personally love a vintage look with a touch of attitude, wearing it with a slight slant that gives it that classic, timeless vibe reminiscent of icons like Jacques Cousteau. On the other hand, some might prefer a more trend-inspired approach, wearing their beanies with a little “pop” above their heads, leaving some space between the cap and their scalp. Some wear it slightly above their ears, while some just wear it exactly as intended, fitted to their head.  What is most important is to wear it in a way that is authentically you. 

Watch caps come in a vast spectrum of colors and weaves, inviting an additional canvas for personal expression. What truly merits thoughtful consideration when choosing a new or additional beanie, however, is what it’s made of.  Most fall into one of the below.

Wool: The Gold Standard

Wool has long been the preferred material for crafting a watch cap, and for good reason. It offers natural breathability and wicking properties, keeping your head warm and dry even in inclement weather. If it was good enough for sailors navigating the high seas, it’s certainly suitable for individuals looking for warmth and durability.

The Advent of Synthetic Fibers

Many modern beanies are crafted from synthetic fibers, such as acrylic or polyamide, and are often blended with wool or other natural fibers. While they might be more budget-friendly, synthetic materials or blends do not breathe as effectively as pure wool or alpaca. However, reliable warmth, ease of care, and affordability make them a suitable choice for those who don’t want to worry too much about losing them during a night out.

The Luxury of Cashmere

Cashmere beanies are incredibly soft and exude opulence, providing unmatched warmth and comfort during colder months. However, there are downsides, such as their vulnerability to inclement weather and the need for more careful maintenance. Nevertheless, for those who prioritize luxury and comfort above all else, cashmere beanies are the epitome of high-end style.

The evolution of the beanie from its functional origins to the runways of today is a testament to the fashion world’s remarkable knack for transforming utilitarian items into unique style statements. Whether you’re embarking on a brisk morning coffee run, grappling with a bad hair day, or preparing for a romantic evening, here are our 11 investment-worthy choices for the approaching colder months.

Based in Normandy, France, Saint James is the OG brand for all things nautical. Since 1898, their now-iconic Breton fisherman sweater has transitioned from being worn on actual shipping vessels to becoming a menswear garment staple. Made from soft wool with a purl knit, their ‘watch cap’ is the perfect fusion of both form and fashion.

Combining Zegna’s Italian sartorial flair with Elder Statesman’s laid-back California luxury, this capsule collection is the collaboration we never knew we needed. You can easily recognize the quality craftsmanship of Zegna in this watch cap, made from the brushed cashmere that Elder Statesman is known for.

NAADAM has built its business on selling 100% Mongolian cashmere directly to consumers, ensuring that this luxurious textile remains accessible to a wide range of people. Available in a beautiful array of colors, their ribbed cashmere beanie is an attractive choice that won’t strain your budget.

This mohair blend beanie is undeniably Missoni, representing the iconic Italian fashion house’s love for color and pattern. The retro fading effect and unique color palette will inject personality into any outfit.

This 100% alpaca fiber beanie, from the niche, minimal and hip brand, Industry of all Nations, is completely undyed, allowing the natural hairs of the fiber to remain in their most pure state. Besides being exceptionally soft and form-fitting, the process helps reduce pollution and conserve resources — both of which are crucial considerations in our current climate.

Equal parts preppy, traditional and modern, this striped Polo Ralph beanie, crafted in merino wool, hits all the right color notes without being too busy. The heraldic lion motif lends it a historical and authentic air.

Madewell Men’s has experienced a notable resurgence under the guidance of its new designer and overall menswear guru, Aaron Levine. It would be challenging to find a better beanie at this price point. Crafted from a recycled cotton-poly blend, the tall cuff invokes an authentic fisherman/watch cap vibe.

Moncler puffer jackets are iconic, truly representing the intersection of high luxury and functionality. Their watch caps are no exception. Although they may come with a high price tag, this heavy cable-knit wool beanie is built to withstand frosty conditions for many years to come.

Leave it to luxury trad brand Drakes to design their beanies based on the traditional seafaring watch caps. Knitted in Scotland, this Geelongora beanie, made from angora and lambswool, offers a softer feel and increased insulation.

Made from the luxurious cashmere that Loro Piana is known for, this intarsia-knit beanie in a Fair Isle pattern exudes personality. It will fit in just as well on the city streets as on the ski slopes.

One of the many reasons Todd Snyder is so acclaimed is his respect for, and application of, the history of menswear to his highly wearable clothing line. His accessories are no exception. Made from a wool-nylon blend, this Donegal beanie features multicolored flecks that add a well-worn personality.

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