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First Date Fashion for Men: The Basics

The purpose of a first date, as defined by Coach Colt, is “not really about getting to know each other. It's about having fun, finding chemistry, and confirming that neither person is cuckoo-crazy." Dressing up in a suit, while it may look great, is not suitable for a first date that is supposed to be fun and relaxed. But “no suit” doesn’t mean “pajamas, yes.” There's a happy medium we should aim for. Let's discuss our options.


Here's a breakdown of how this Spring date outfit comes together: 

- The dark peacoat is a classic piece with a sense of style and maturity. It's warm enough for a chilly day but also structured to add a sharp edge to the overall look. 

- Underneath the coat, the bright orange sweater provides a striking contrast, making the outfit stand out. 

- Slim-fit jeans are a staple in casual fashion, but here they're smartened up by the choice of footwear and the layers above. 

- The rugged lace-up boots are both practical for an outdoor setting and fashionable, complementing the earthy tones of the setting and the season. 

Overall, the outfit is good, balancing smart and casual elements with a touch of bold color to make a more memorable impression.


For our first summer date outfit, we have a more classic yet relatively casual style, perfect for a chic setting: 

- A pair of dark gray chinos is a comfortable, step-above-casual trendy option. 

- Wear a simple back crew neck T-shirt with a small logo for a simple, understated look. 

- A pair of white leather sneakers with slight red accents strike a balance with the dressy white leather and the pop of color and personality from the red accents on the heel. 

- Wear a simple silver mesh band watch to compliment the overall minimalist style of the outfit. 

This outfit is perfect for a casual first date at the coffee shop or the park. It's relaxed yet stylish, ideal for an easy-going guy who still cares about his appearance. The colors are neutral and complement any skin tone, and the clothes should fit well to avoid looking untidy. For our second example, we have a more casual, sporty look, perfect for a date bike riding at the beach on a hot summer date - but with the same laid-back, easygoing style. 

- He is wearing a loose-fitting, short-sleeved t-shirt in a neutral color, which offers comfort and ease of movement, suitable for physical activities. 

- His shorts are patterned, which adds a bit of fun and personality to the outfit. They are also an appropriate length for cycling, allowing for flexibility and airflow. 

- He’s picked practical sneakers for outdoor sports. 

- His headband keeps hair and sweat away from his face, which is super practical for any active date. 

Fall/ Autumn 

For our fall/ autumn example: 

- He is wearing a teal blue pea coat, which offers a smart-casual look while providing warmth. The coat's color is unique and can show off some personality without being too loud. 

- The lighter gray sweater keeps the outfit looking polished and looks great on its own when the date moves to a warmer indoor setting and they take off their coat. 

- The blue jeans are a must-have casual staple, but their slim fit adds modern style to the outfit. (The jeans' color also complements the coat's blue tones.) 

- His footwear consists of brown leather boots, which are practical for walking in potentially uneven terrains of a fall environment and add a rugged yet put-together touch to the overall look. 

- Accessorized with a beanie - for keeping warm and adding an easygoing vibe to the outfit. 

For a more winter-ready fall outfit: 

- The camel-colored duffle coat is the statement piece of this outfit. And it's practical for keeping warm. 

- Underneath, the black shirt keeps the look simple and versatile, allowing the coat to be the focal point. 

- The ripped black jeans add a modern, edgy touch to the outfit, offering a contrast in texture and style to the classic coat. 

- The brown lace-up boots coordinate well with the coat and suggest readiness for walking through city streets or parks. 

- The sunglasses accessorize the outfit, contributing to the laid-back yet thoughtfully put-together appearance. 

Both examples are perfect for that relaxed but stylish vibe.


And lastly, for a winter date: 

- The red and black checkered jacket is a bold statement piece, typically lumberjack-style, which gives off a rugged and masculine vibe. 

- The black knit beanie and the thick, patterned scarf are essential for staying warm and comfortable in snowy or windy conditions. They also add texture to the outfit. 

- Classic blue jeans with an Eazybelt is a timeless choice that pairs well with the checkered pattern of the jacket, maintaining a casual look while providing durability and warmth. 

- And, of course, gloves; practical for the weather and complete the winter-ready look. 

See more men’s winter outfits here: Our top 7 winter menswear essentials.

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