Dress shorts, once considered a contradiction in terms, have emerged as a stylish summer staple for men. Today, most popular pants styles—from khakis to sweats to jeans—are available in lightweight versions for warmer months. However, one category that long lacked warm-weather alternatives was formal trousers. Fortunately, that gap has now been filled.
This development offers a welcome solution for men attending a vacation lunch, relaxing at a beach club, or visiting friends in the countryside. In such settings, gym shorts won’t suffice. That’s where dress shorts come in—designed to provide sophistication and comfort without sacrificing style.
When it comes to styling, there are two primary approaches, exemplified by fashion icons Thom Browne and Rick Owens. Browne’s style favors neat tailoring and a shorter fit, ideal with a button-down shirt or a classic sweatshirt. Owens leans toward oversized, loosely structured silhouettes cut longer, perfect for pairing with casual tees or layered garments. Regardless of the approach, the fit should avoid being too tight, as strained seams can compromise the look. As for materials, cotton, linen, and lightweight wool remain preferred choices for both breathability and structure.
COS Tailored Drawstring Linen Shorts: Best Overall Dress Shorts
For a versatile, all-purpose option, the tailored drawstring linen shorts by COS stand out. As a premium brand under the H&M umbrella, COS offers a product that is both well-made and stylish. The tailored yet relaxed fit, lightweight linen fabric, and neutral color make them suitable for both formal and casual summer outfits.
The drawstring waist introduces a casual vibe, yet the shorts remain appropriate when worn with an unstructured linen blazer or an oversized shirt. To elevate the look, pairing them with Derby shoes and black socks is recommended. For a trendier twist, backless loafers could also work.
GAP Linen-Cotton Shorts: Best Budget Option
For those seeking a more affordable option, GAP’s linen-cotton shorts are an excellent choice. Flat-fronted and mid-length, these shorts are simple and effective. Although budget-friendly, they visually resemble designs from contemporary Scandinavian brands.
The lower waistline necessitates mindful styling—tops should be long enough to cover the waistband. Ideal pairings include untucked T-shirts, polos, or button-down shirts. A French tuck can also help avoid a boyish or overly casual appearance.
Todd Snyder Tropical Wool Tab Shorts: Best for an Upgrade
With a 7-inch inseam, Todd Snyder’s Tropical Wool Tab Shorts are among the shortest in the category, appealing to those comfortable showing more leg. Since Prada popularized shorter shorts a few years ago, they have seen a resurgence in men’s fashion, particularly among those moving away from baggier styles.
The shorts can be paired with a matching tailored jacket for a cohesive look. Even without the jacket, pairing these with relaxed-fitting tops can maintain a modern silhouette. It’s important that tops do not extend past the hemline of the shorts to preserve visual balance.
Stòffa Plain Front Washable Shorts: Dressiest Dress Shorts
Stòffa’s Plain Front Washable Shorts represent the upper echelon of refined summer dressing. The New York-based brand combines cotton and linen in a shorter, wider cut that provides a roomier fit around the thighs. This design lends a dressier feel compared to typical casual shorts, further enhanced by an attached belt.
Attention to detail is a hallmark of Stòffa’s craftsmanship. Buyers can even choose the preferred hem finish. For maintaining a minimalistic aesthetic, the plain hem is suggested.
Polo Ralph Lauren Relaxed Fit Pleated Twill Shorts: Best Pleated Shorts
Polo Ralph Lauren’s relaxed fit pleated twill shorts add classic charm to modern summer wear. Designed for comfort and style, the pleats offer a sophisticated touch while still maintaining a relaxed overall vibe. The tailored structure allows them to be dressed up or down, depending on the occasion.
Pairing these with leather footwear and a tucked-in or French-tucked shirt can elevate the overall appearance, making them suitable for both daytime errands and evening outings.
Auralee Shorts: Best for Loose Fit and Style
Japanese brand Auralee excels in creating shorts that strike a balance between relaxed comfort and sophisticated design. For those who favor looser silhouettes and avoid slim-fit cuts, Auralee’s options are ideal.
The longer length of these shorts makes them versatile. They can be worn casually with sneakers and a loose tee or dressed up with a button-down shirt and leather shoes for a more refined look. Grooming and accessories like a well-trimmed beard further enhance the outfit’s polished effect.
Alex Mill Pull-On Field Shorts: Best Linen Option
Alex Mill’s pull-on field shorts offer a low-effort solution for summer styling. These linen shorts are both easy to wear and smart in appearance, making them ideal for hot-weather dressing.
The flax linen provides texture, while patch pockets contribute to the overall design. These shorts pair effortlessly with most summer shirts, allowing men to maintain a clean look with minimal effort.
In summary, dress shorts have become a crucial part of the modern man’s summer wardrobe. With options ranging from high-end to budget-friendly, tailored to relaxed, and minimalistic to bold, there is a pair for every preference and occasion. Whether preparing for a vacation brunch, a casual evening out, or a weekend getaway, the right pair of dress shorts ensures both comfort and style.
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