• Top: Polo or t-shirt
• Pants: Chinos or jeans
• Shoes: Sneakers
• Outerwear: Lightweight jacket or parka

Dinner Date

Now it is time to lift your game. You can pretty much wear what you would to a bar date, just with a few tweaks. Wearing some kind of collared top is important, be that a polo or a nice crisp shirt. We suggest a neutral color collared shirt. Leave the jeans at home and go for chinos or a nice pair of trousers. This is the best time to wear a blazer if it is a bit chilly. For shoes, some form of a dress shoe, like an Oxford or bogue is best. Even a Chelsea boot can suffice. Don’t wear a suit though, especially with a tie. It is too formal and gives off the wrong impression.

• Top: Collared shirt, neutral colors
• Pants: Chinos or trousers
• Shoes: Dress shoes such as Oxford or brogue, Chelsea boots
• Outerwear: Blazer
• Accessories: Watch, nice belt

Outdoor Date

Just because you are outdoors and taking part in an activity doesn’t mean you can throw style out the window. You can still look good while being active and impress your date. If the weather is warm and you plan on going for a hike, a pair of shorts and a t-shirt are perfectly acceptable. As are trainers or sneakers. This is also the one occasion when wearing a cap is ok, just make sure she shes you without it so she knows you aren’t trying to find anything.

If it is during the colder months, you can still get away with chinos or jeans, although it might be better you wear a pair of flexible pants, although try and stay away from sweatpants. A sweater or sports jacket is also great to keep you warm. Similar to warm weather, a pair of sneakers is fine.

• Top: T-shirt
• Pants: Chinos, jeans, or pants
• Shoes: Sneakers or trainers
• Outerwear: Lightweight sports jacket or sweater
• Accessories: Cap

Above All, Be Confident

Whatever you decide to wear, do so with confidence and flair. You have to trust in your style and the clothes you wear. If you think you look good, you will feel good and this will come across when talking with your date. If you are constantly worrying if your shirt fits or if you chose the right shoes, it will affect your confidence. Have faith in your style and rock it with confidence. Your date will no doubt be impressed and you might even get a pash at the end of the night.