Ben Sherman Brings Timeless Style to the Fairway and Beyond

For decades, Ben Sherman has built its reputation around clean lines, British-inspired style and clothing that bridges the gap between casual and refined. While the brand has long been associated with music, culture and classic menswear, its growing golf-inspired apparel lineup continues to impress golfers looking for something different from the traditional athletic golf aesthetic.

Last year, Chicago Golf Report reviewed Ben Sherman apparel and highlighted the company’s ability to blend lifestyle fashion with functional golf wear. After spending additional time with several new pieces from the collection this spring, it’s clear Ben Sherman continues to carve out a unique niche for golfers who appreciate versatile clothing that looks equally comfortable at the club, in the office or during a night out.

For this review, Chicago Golf Report tested two Ben Sherman polo shirts — the Azure Polo Shirt and the White Print Polo Shirt — along with two pairs of Four-Way Stretch Pants in Light Grey and Navy. The apparel was worn during rounds at Pine Meadow Golf Club in Mundelein and Cantigny Golf in Wheaton, providing an excellent opportunity to evaluate performance during both walking rounds and changing spring weather conditions in Chicagoland.

A Refreshing Alternative to Modern Golf Apparel

One of the most noticeable things about Ben Sherman’s golf collection is how distinct it feels compared to much of today’s golf apparel market. Many modern golf brands lean heavily into athletic styling, oversized logos and ultra-technical aesthetics. Ben Sherman instead takes a more refined approach.

The result is apparel that feels polished without appearing overly formal. The shirts and pants are clearly designed with golf in mind, yet they avoid looking like “performance uniforms.” That versatility becomes a major advantage for golfers who move between work, social events and the course throughout the day.

At a course like Cantigny, where players often linger after the round for dinner or drinks on the patio, the Ben Sherman pieces fit naturally into the environment. The same held true at Pine Meadow, where the relaxed but stylish atmosphere complemented the understated look of the apparel.

Azure Polo Shirt: Clean, Modern and Comfortable

Ben Sherman Azure Polo Shirt

The Azure Polo Shirt immediately stood out because of its vibrant but tasteful color. The shade delivers enough personality to stand out on the course while remaining versatile enough to pair with a wide variety of pants and layering pieces.

Fit is always an important factor with golf apparel, and the size large offered a modern tailored fit without becoming restrictive. Some athletic golf polos today can feel excessively slim or overly synthetic. Ben Sherman strikes a strong balance here. The shirt has structure and shape without sacrificing comfort.

The fabric itself feels soft and lightweight, making it comfortable during warmer temperatures while still maintaining enough substance to avoid feeling flimsy. During a breezy spring afternoon at Pine Meadow, the polo remained comfortable throughout the round and moved naturally during the golf swing.

The subtle detailing and clean collar design also deserve mention. The polo maintains a polished appearance even after several hours on the course, which is not always the case with lightweight golf shirts that can wrinkle or lose shape quickly.

Another strength of the Azure Polo is its versatility away from golf. This is a shirt that could easily be worn to dinner, casual business meetings or social events without feeling like dedicated athletic apparel.

White Print Polo Shirt: Stylish Without Being Loud

Ben Sherman Polo Shirt

The White Print Polo Shirt may have been the biggest surprise of the group. Patterned golf shirts can sometimes cross the line into overly flashy territory, but Ben Sherman keeps the design tasteful and understated.

The print adds visual interest while remaining subtle enough to work in a variety of settings. Paired with the Navy Four-Way Stretch Pants, the look felt modern and sophisticated without trying too hard.

Performance-wise, the White Print Polo delivered similar strengths to the Azure version. Breathability remained excellent during a sunny afternoon round at Cantigny, and the fabric allowed for unrestricted movement throughout the swing.

One of the most impressive aspects of both polos is that they avoid the “plastic” feel common in many performance golf shirts. Ben Sherman appears to prioritize comfort and wearability first while still incorporating enough stretch and moisture management for golf functionality.

For golfers who appreciate fashion but do not want to look overly trendy, this shirt hits an appealing middle ground.

Four-Way Stretch Pants: The Hidden Star of the Collection

Ben Sherman Four-Way Stretch Pants

While the polos impressed, the Four-Way Stretch Pants may have been the standout products in this review.

These pants offer a level of versatility that many golfers will appreciate immediately. The modern tapered fit looks sharp without becoming too slim, and the stretch material provides excellent mobility throughout the golf swing.

Walking 18 holes at Cantigny can involve a fair amount of movement, uneven lies and elevation changes, and the pants handled all of it comfortably. The four-way stretch fabric performs exactly as advertised, allowing the pants to move naturally without feeling restrictive.

Comfort around the waist and thighs remained consistent throughout the round, which can be an issue with more structured golf pants. At no point did the material feel stiff or heavy.

The Light Grey version pairs exceptionally well with brighter polo colors like the Azure shirt, while the Navy pants offer maximum versatility and could easily transition into business casual environments.

Another major strength is how clean the pants look compared to many athletic golf joggers currently dominating the market. Ben Sherman’s pants maintain a traditional silhouette while quietly incorporating modern performance features.

For golfers who still prefer a more classic golf look — especially at traditional facilities or private clubs — these pants provide an excellent alternative to joggers or aggressively tapered athletic fits.

Perfect for Chicagoland Golf

Testing the apparel during spring golf in the Chicago area highlighted another important strength: adaptability.

Spring golf in Illinois often means fluctuating temperatures, wind and changing conditions within a single round. The Ben Sherman apparel handled those transitions extremely well. The lightweight materials remained breathable during sunny stretches while still offering enough structure for cooler conditions.

That flexibility ultimately defines the collection. Ben Sherman is not trying to compete directly with hyper-technical athletic golf brands. Instead, the company is offering stylish apparel for golfers who value both appearance and comfort.

Final Thoughts

Ben Sherman continues to establish itself as a compelling option for golfers seeking apparel that blends modern golf functionality with timeless style.

The Azure Polo Shirt delivers clean, versatile color with excellent comfort. The White Print Polo adds personality without becoming overpowering. Meanwhile, the Four-Way Stretch Pants in both Light Grey and Navy may quietly be among the most versatile golf pants we’ve tested this season.

What makes these pieces particularly appealing is their ability to move seamlessly beyond the golf course. In many ways, that versatility reflects how golfers actually live today. Players increasingly want apparel that works throughout the entire day rather than clothing designed exclusively for four hours on the course.

For golfers who appreciate understated style, comfortable fits and apparel that transitions naturally between golf and everyday life, Ben Sherman’s latest collection deserves serious consideration.

Whether walking the fairways or enjoying an afternoon round, Ben Sherman proves that classic style still has a place in modern golf apparel.