3 Date Night Outfit Ideas That Will Help You Impress Her

Your choice of outfit on a date night can make or break your chances of impressing her. Get it right and you’ll exude confidence, which is always attractive. Get it wrong, and you’ll come across as try-hard or disinterested.
With that in mind, we’ve put together three date night outfit ideas that will help you make the best impression. From what to wear on a first date to what to wear on a third date, we’ve got you covered.

What to Wear on a First Date

When it comes to first dates, it pays to err on the side of caution. You want to look your best without feeling overly dressed up or too underdressed. Smart casual is one of the best date night outfit ideas you can opt for. Go for something smart on the top – a shirt, knit, polo, or any other neat-looking tailored piece. Then pair this with something casual on the bottom, such as a pair of chinos or smart jeans. Choose a color and fabric combination that reflects your personal style and don’t be afraid to experiment a little. Footwear is important on your first date – aim for a style that’s neat and not too clumpy or overly dressy. A classic pair of leather Derby shoes is a great option. Finish off the look with some timeless accessories like a nice watch or leather belt.

What to Wear on a Second Date

On a second date, you’ve got more of a chance to show off your unique sense of style. You can take the core wardrobe pieces you wore on the first date, but take it to the next level by omitting a few extra pieces that will bring the entire look together. On top, pick items that will help you stand out from the crowd – choose a casual Oxford shirt, a checked shirt, or a Henley shirt. On the bottom, keep it neat, but opt for something more adventurous like slim-fit corduroys or slim-fit jeans. Finish off with a stylish pair of leather brogues or loafers. Accessorize with a nice scarf, printed pocket square, or a beanie for winter dates. Ultimately, the goal is for your outfit to reflect your personality as well as your individuality.

What to Wear on a Third Date

At this stage, you can up the stakes and start to demonstrate your sartorial flair. For a third date, a smarter-casual look is a way to go. On top, go for a cotton Oxford shirt with a nice blazer or a cardigan over your ensemble. As for the bottom, elegantly tailored dress trousers are the perfect complement to the look. Round off the look with a pair of stylish leather shoes and accessorize with a smart belt and tailored fit watch. Remember, less is more – focus on subtle details like an interesting lapel pin instead of going overboard with too many colors, patterns, or textures.


Choosing the right outfit on a date night can help you make the best impression. From what to wear on a first date to what to wear on a third date, no one-size-fits-all outfit works for every occasion. Instead, it’s about finding the perfect balance between being smart and casual and tailoring your look to suit the occasion. With these three date night outfit ideas, you’ll be well on your way to making a lasting impression.