What to Wear on a Date – A Complete Guide for Him and Her

So, you’ve finally mustered the courage to ask the person you’ve fancied for months on a date, and now that the day is almost upon you, you’re stumped for ideas on the ideal outfit! Fret not, we’re here to help you make that perfect first impression regardless of the date you have planned.

Keeping it Casual

For Her – Meeting at a coffee house, perhaps followed by a stroll through some quaint bookstores? Ladies, the key is to keep it casual and comfy. Look effortlessly chic with a pair of white shorts or ripped boyfriend jeans paired with a cute cami. Throw on a breezy linen ladies’ shirt for a dash of chutzpah. Complete the look with a messy bun, a pair of round statement shades, colourful espadrilles, and a neutral satchel. 

For Him – Guys, make the most of the season with pastel chinos or shorts clubbed with a good old polo. You could even mix it up with a mandarin collared shirt or a white short kurta for men. Don’t get too carried away with the laid-back look though. Avoid flip-flops or sandals. Opt instead for suede moccasins. Last of all, don’t be afraid to experiment with a pop of colour here!

Cocktail Night

For Her – Drinks and dancing is a first date cliché we never get bored of! Girls, pick an outfit that flatters your form without looking too eager to please. You can’t go wrong with your favourite little black dress, a pair of pointed toe black pumps and a wristlet or a quilted side body bag. Keep your hair undone, and go for a subtle smoky-eye look to complement the outfit. Avoid anything that needs constant readjustment and don’t, under any circumstances, wear new shoes. 

For Him – Men, ever heard the saying that a man who can cut an impressive silhouette in a button-down shirt is worthy of a second date? The key to this look is fit and fabric. Wear a slim shirt in a breathable fabric to avoid the dreaded sweat patch. Stick to a darker shade and feel free to play around with textures. Tuck the shirt into a pair of straight cut denim jeans and ditch the belt. Elevate the look with a pair of monks or derby brogues, with a fresh, citrus cologne that will generate interest without assaulting the nose.

Pulling Out the Big Guns

For Her – Taking things up a notch to make your first date a night to remember with dinner reservations at that restaurant with the celebrity chef? Ladies, if you feel good in what you’re wearing, you’ll look good anyway. A great pair of skinny pants that shows off your figure paired with a silk tank is a great idea. Stand out with a statement piece of jewellery and a sequined clutch, and complete the look with a classic pair of black stilettoes. Refrain from painting your face too much; just pull your hair back into a high ponytail and wear some kohl, mascara, and lip gloss for a natural look that enhances your features, not overwhelms them.

For Him – Pairing a blazer with jeans allows all you guys out there to heighten your outfit by adding detail and texture as well as achieve that refined yet relaxed look with ease. Stick to the classics and pair a slim-fit black sports coat or blazer with some skinny jeans and a white or powder blue tee. Spruce it up with a pair of leather loafers, your best cologne, and well-groomed facial hair. Finally, to throw in that fun element and own the look, pair your loafers with some spunky, colourful socks.