First impressions last forever, always dress the part. The secret to an outstanding impression is dressing to match the venue and the personality you're going to see. Below are several date night ideas to try.

Chic and casual

Keep it stylish and simple. A regular meetup doesn't require you to be extra. Keep your outfit comfy and casual so you can focus on making a connection. A simple pair of jeans with a plain t-shirt and a jacket can do the trick. And finally, sneakers and sandals are a great touch for a casual look. However, make sure they are clean.

Elevated casual

I took this photo while on photography assignment at Pitti Uomo, the largest menswear fashion tradeshow in the world, in Florence, Italy. At Pitti there is a square where key players in mens fashion network with eachother and show their sartorial style.
Photo by Mariya Georgieva / Unsplash

If your date is an indoors person you might want to impress a little. Shirts and a coloured jeans are the perfect combo. Grab a jacket if the weather is cold.For footwear, a chukka is the perfect in-between shoe that has a relaxed vibe yet is much more polished than a sneaker. It gives just the right amount of cool vibes.


If you're going on a formal date, you should definitely dress up and show that you've made an effort. A wool blazer and dress pants in coordinating neutral colours can't go wrong. This keeps your outfit grounded and elevated, allowing the focus to be on your conversation rather than your outfit. With a tie and pocket square, you can add a subtle pop of colour. Combine it all with a leather belt and your favourite dress shoes in a rich cognac colour.

Modern sophistication

Are you meeting your date downtown for craft cocktails? You'll want to put together an elevated outfit that is also appropriate if there is a dress code. Choosing a sport coat over a blazer softens the formality, and a pattern like a tonal check adds a touch of personality. Add a tie and a pair of derby shoes for the finishing touch. A pocket square is a great way to add a touch of class to your outfit. It doesn't have to exactly match your tie—just make sure they complement each other.

Look smart

Confident elegant man
Photo by Adeolu Eletu / Unsplash

Starting with a windowpane oxford shirt and chinos is a good way to create a polished look that works for a variety of date night plans. If it's cold outside, add a sweater for a more formal look. Merino wool, for example, provides excellent warmth while remaining lightweight and non-bulky. Finish with a neutral-colored sport coat and a belt after tucking in your shirt. Leather loafers are the perfect finishing touch.

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