5 Casual Summer Date Outfits for Men

Summer means there are lots of opportunities to date and find that special someone. Whether you are planning on a beach date, a walk down your town’s main street in the sun, or a late-night get-together with your friends and a potential significant other, you need to know what to wear to look your best.

Fortunately, you have lots of options in terms of quality casual summer date outfits. Let’s break down five of the best summer date outfits to put together in detail.

Button-Down and Jeans

You can’t go wrong with a summer staple: a button-down shirt and jeans. While jeans can be a bit hot for your legs depending on the weather and humidity, they go perfectly with a classy button-down shirt, which can be either a long sleeve or T-shirt based on where you plan to take your date.

A button-down and jeans are a perfect ensemble for a more formal date or for an occasion where you want to impress your beau.

Polo Shirt + Shorts

Alternatively, you can go with a summer date night classic: a polo shirt, white or colored socks, great shoes, and shorts. Polo shirts are a little more elegant and formal compared to T-shirts, but they aren't so formal that you’ll look out of place at a typical restaurant.

More importantly, polo shirts are usually quite comfortable, and you can find them in a variety of colors, styles, and sizes.

As far as shorts go, you can always pair the perfect polo with high-quality micrograph Gurkha shorts. Vintage 1946’s Gurkha shorts are available in many different colors and sizes. More importantly, these shorts are designed with a specialized quick-drying fabric. Therefore, if you get a little wet from a summer afternoon thunderstorm, you can rest assured your shorts will dry sooner rather than later.

These quality shorts come with interior mesh pockets, a secure zippered rear pocket, and a gusseted crotch for functional and comfortable movement.

Tank Top, Overshirt, and Shorts/Trousers

You can keep things casual with a basic setup including a tank top, over shirt, and your choice of shorts or trousers. A tank top and over shirt give you the flexibility of being able to take off an upper layer if it gets too hot while also allowing you to button up the over shirt if you want to appear a bit more put together.

Windjammer shorts are perfect for pairing with a tank top and/or over a shirt. For example, Vintage 1946’s windjammer shorts are made of a stretchable and quick-drying fabric. The hybrid material used for each pair of shorts is ideal for walking on land or taking a dip in the ocean. Thus, you can easily wear these windjammer shorts to a beach date or a pool party without worrying. For added comfort and versatility, they come with an elastic waist, interior mesh pocketing, and other benefits.

Monochrome Date-Night Set

Monochrome date night getups can look great when done properly. You should pick a matching polo shirt and trousers or shorts that are the same shade; of course, that shade should also go perfectly with your skin tone. Add in some neutral-colored shoes in shades like white, gray, or beige, and you'll be set.

However, just make sure that your chosen polo shirt and trousers are made of a comfortable material. The last thing you want is to sweat up a storm in the middle of your date with a woman you want to impress!

Tropical Casual Outfit

If you're keeping things super casual, consider putting together a tropical casual outfit. Wear a Hawaiian pattern shirt or some other button-down, but keep it open. Then pair that with a colored shirt or tank top and casual accessories, like a few bracelets, a necklace, and some sunglasses. It's perfect for a beach date or an informal hang-out with not just your date but also a few friends.

Sport shorts, such as Vintage 1946’s options, can also work with tropical casual getups. But keep in mind that these shorts are a little shorter than average, so they’re only ideal for super casual occasions or dates.


While the above five summer date outfits are great places to start, they are by no means the only outfits to try. In truth, there are dozens of different summer date outfits to try on for size and experiment with. Consider your style and your unique aesthetic, and don't hesitate to check out Vintage 1946’s Spring collection for quality shorts and other men’s apparel today!