These Dress Shirts Can Upgrade a Man’s Entire Wardrobe
Good foundation pieces are essential to building a versatile, polished wardrobe. The quality dress shirt is the perfect compromise between structured corporate offices, relaxed weekend gatherings, romantic dinners, and formal weddings. Watching out for cuts, fabrics and collar shapes makes it easy to find the right shirt for any occasion.
For years, Brooks Brothers has been the gold standard in men’s tailoring. Here’s a fair assessment of how nine of their essential dress shirts measure up across a variety of fits, fabrics and styling situations.
1. Stretch Herringbone Dress Shirt
I bought this sleek black shirt for my husband before a weekend of evening events, and it became an instant favorite. It’s made of Supima cotton in a fine herringbone weave, and is super soft, with the perfect amount of stretch for ease of movement. English spread collar nicely frames the face, with or without tie. Perfect with black or charcoal suits for formal events, but he usually wears it unbuttoned with dark jeans and leather loafers for a sharp, smart casual night out.
2. Non-Iron Candy Stripe Shirt
I picked this up for my brother, who needed something to break up his rotation of plain white shirts. The candy stripe pattern adds subtle energy to traditional tailoring, while the iconic button-down collar keeps everything neat under a jacket. The bright blue hue brings a welcome pop of color to daily office wear. It excels during client presentations or routine office days, especially layered under a navy blazer with tailored tan chinos.
3. Pinpoint Oxford Windowpane Shirt
A friend wore this to an outdoor party, and the teal windowpane pattern was the first thing I noticed. It's a nice change from the usual solid blue shirts. The Ainsley spread collar gives it a sharper look, while the non-iron pinpoint Oxford fabric helps it stay neat throughout the day. I thought it looked especially good with dark gray tailored trousers.
4. Pure Supima Cotton Ground Stripe Shirt
If you prefer classic tailoring to trendy cuts, this ground-stripe shirt is about as traditional as it gets. Vertical stripes create a clean, lengthening profile that feels naturally formal. Made from pure extra-long staple Supima cotton, this regular finish shirt prioritizes breathability and natural softness. The broad English spread collar accommodates fuller tie knots effortlessly, making it a reliable option for executive meetings and formal ceremonies when styled with a charcoal wool suit.
5. Stretch Pinpoint Oxford Check Shirt
I recommended this one to a friend looking for something subtle yet memorable for date nights. The Ainsley collar lies flat against the jacket lapels, while the wrinkle-resistant, stretch-pinchpoint fabric accommodates everyday movement without stubborn creases. It fits naturally into cocktail receptions and refined work environments, styling beautifully with navy chinos and brown leather dress shoes.
6. Non Iron Dot Dress Shirt
My husband wears this dark blue version whenever he wants an outfit that feels deliberate but not overly stiff. The classic barrel cuffs and Ainsley collar keep the playful pattern grounded in classic design. It works exceptionally well for creative offices or casual dates, especially when paired with an unstructured suit and clean white sneakers for a modern, approachable feel.
7. Explorer Collection Gingham Shirt
I bought this for my brother and the fit gives him plenty of room to move without looking baggy. The warm peach gingham pattern adds instant brightness to an outfit. It’s a great pick for warm weather outdoor weddings and casual Fridays, looking natural with light beige chinos or classic blue denim.
8. Big & Tall Polo Button Down Windowpane Shirt
My friend, who usually struggles with stiff dress shirts, swears by the comfort of this cut. The soft grid of the windowpane keeps the pattern subtle and dependable for larger frames that want a tailored touch. Dark wash jeans and leather boots are no problem for it, nor are long travel days and informal business dinners.
9. Linen Londoner Collar Shirt
Nothing beats pure linen for staying cool. Made in woven Irish linen, this shirt features a wide Londoner spread collar, for an effortless, resort-ready style. My husband took this on our last getaway and the breathable texture kept him comfortable in humid heat. It’s a staple for beach weddings and summer dates, and looks best with lightweight cream linen trousers or olive green chinos.
A good dress shirt should make it easier to get dressed, not harder, at the end of the day. Investing in a few versatile patterns and reliable fabrics means you have a go-to option ready, no matter what the dress code calls for.
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