The classic men's dress shirt remains a timeless wardrobe staple, transcending style eras with its versatile design. Experts emphasize that fit and proportion are paramount, with a well-fitting dress shirt conforming to the body without being too tight or too loose.

Justin Berkowitz, a men's fashion director with seven years of experience at Bloomingdale's, advises that a good dress shirt should follow the body's shape. If excess fabric billows at the waist when tucked in, the shirt is too large, while buttons straining across the chest or belly indicate it's too tight. Collar shape and size are also crucial, with the collar needing to be proportional to jacket lapels. Slimmer collars complement narrower lapels, and vice versa.

Berkowitz recommends brands such as Eton for their quality and value, noting their Signature Twill Shirt as a notable option due to its single-cuff design, wrinkle-free fabric, and structured fit. STANTT is highlighted for its diverse range of fits catering to individual body types.

Dress shirt materials vary, with cotton being the most traditional choice, often in weaves like poplin or twill. These cotton shirts pair well with suits made from natural fibers such as wool and cotton. Modern dress shirts may incorporate stretch for enhanced performance, and a category of true performance dress shirts made from synthetic fabrics like polyester has emerged, focusing on temperature regulation and ease of movement. These synthetic options are also beneficial for travel and often pair well with performance fabric suits, typically without a tie.

Styling a dress shirt depends on the occasion. For office wear, Berkowitz suggests pairing a shirt with a softer collar with an unlined sport coat, five-pocket pants, and clean sneakers. For spring or summer weddings, a stiffer collar in a solid color, like white or a soft pastel, paired with a seasonal suit in linen or tropical wool, and suede lace-ups or loafers is recommended.

Collar types are also important. Straight point collars and spread or semi-spread collars are common. Point collars offer a more modern aesthetic, while spread and semi-spread collars lean towards a traditional look, complementing Italian-inspired tailoring. Wing collars are typically reserved for formal occasions.

While classic solids and small patterns remain evergreen, a 'back-to-basics' trend is currently influencing dress shirts, with bolder patterns more commonly found on sport shirts made from fluid fabrics.

Several brands offer highly-rated dress shirts. Quince's Organic Cotton dress shirt is noted for its high yarn count, wrinkle resistance, and antimicrobial properties. Eton's Signature Twill Shirt is praised for its wrinkle-free fabric and structured fit. The Tie Bar offers non-iron shirts with playful check patterns. STANTT Essentials provides contemporary fit dress shirts with a French placket and cutaway collar. Bonobos is known for its Jetsetter Stretch Dress Shirt, available in various patterns and fits. Lululemon's New Venture Slim-Fit Long Sleeve Shirt is a performance-oriented option with sweat-wicking fabric. Van Heusen's Regular-Fit Dress Shirt is a popular choice on Amazon for its classic fit and wide color selection. State & Liberty offers moisture-wicking, stretch material shirts with a tailored fit. Calvin Klein's Slim-Fit Performance Dress Shirt is a machine-washable, moisture-wicking option. Charles Tyrwhitt provides lightweight, breathable twill shirts in multiple fits and customizable options. Joseph Abboud's Twill Egyptian Cotton Dress Shirt offers value with premium cotton. J.Crew's Ludlow Premium Fine Cotton Dress Shirt is crafted with fine yarns for a smooth finish. Tommy Bahama's IslandZone shirt is lightweight and moisture-wicking with stretch. Vineyard Vines offers moisture-wicking, quick-drying shirts with a relaxed yet tailored look.