We’ve all been there, excited for a first date, day dreaming and romanticizing the events ahead and suddenly you realize… you don’t know what to wear! Now before you press the panic but and alert the U.S. Marshalls let’s think this through. While it may seem daunting at first, preparing for a date is easier than one might expect. All it takes is a solid foundation backed by steady principals and you will forever be ready for the first date. Day or night, outside or indoors The Tainted Gent has got you covered. Now let’s get into what to wear on a first date for guys.

Find Your First Date Staple Pieces

Your staple wardrobe pieces will forever be your go tos. These are the pieces that you know you can rely on to pull a look together fast. If you do the work and find pieces that suit your body type and personality well, you will never be without something to wear. In order to help yourself find those staple pieces ask yourself these questions.

• What in my closet do I really like and looks good on me?

• What do I get a lot of compliments on when I wear it?

• What styles of clothing do I gravitate toward often in my wardrobe?

More than likely if you’re able to answer any of these questions, these are your staple pieces. If you own multiple of it and you really love the way it looks on you specifically, it’s more than likely a staple in your wardrobe.

What are staple pieces?

A staple wardrobe piece is a piece of clothing that works especially well for YOU. It is a garment that reflects your personality well and doesn’t require much styling. When chosen correctly staple pieces have the power to pull an otherwise basic look together or even stand alone.

What are basics?

Basics on the other hand are just that. They require styling and accessorizing so that your outfit doesn’t fall flat. Basics can be treated as foundations to an outfit but they do not make the outfit.

Know Your Basics

Basics work well for everyone. But knowing which silhouettes fit you best can help you to better choose your basics for a date night.

Here are a list of basics all guys can wear for a first date:

• Basic Tees: Basic tees have the power to be the foundation of many outfits. If you style these tops properly the outfit opportunities will be wondrous.
• Black Jeans / Dark Wash Jeans: While you don’t necessarily need both; these jeans are great for giving a slightly dressy look without feeling overly dressed up.
• Black Sweater / Knits: Black is suggested simply because of its versatility and resistance to visible stains. Because accidents do happen. Even on first dates. But you can purchase this basic as a turtle neck / mock neck if you prefer.
• Black Shoes: Loafers, Dress Shoes, Boots, etc.
• Button Down Shirts: These are just always nice to have handy. Even if this isn’t a go to for you. They make for good layering pieces.
• Hats: For emergencies. Everyone has bad hair days.

Now that we’ve go that covered. It’s time for the good stuff. Here are some staple pieces you can add to your wardrobe so you’ll always know what to wear on a first date for guys.

What To Wear To A Date In The Morning For Guys

The Coffee Date

So when it comes to a coffee date more than likely you’ll be sitting at a table. Therefore we’re going to focus on the upper half. More than likely you’re going to speak with your hands so you’ll want to accessorize but for the star of the show, a cardigan seems appropriate. This black textured cardigan from COS is a safe and easy choice. To style it, simply layer. A basic tee paired with the right accessories could go a long way. Of course this isn’t the most exuberant option, however, it’s coffee and your date will probably be half awake anyway. But there are no rules so choose a knit that fits your personality best.

The Brunch Date

Brunch… is tricky. While you may be used to going with your friends on Sunday to drink and party, a date is a bit different. However, the spirit of brunch is all the same and you should be prepared for anything. These cropped creased pants from YONY do just that, while also feeling durable enough to stand the test of time. To outfit these pants, I’d suggest something along the lines of a camp collar shirt. Maybe throw on some shades and a high top sneaker and you’re good to go!

The Gym Date

To wrap up our list of unconventional morning dates we have the gym date. For the fitness lovers this is a fun activity to get to know someone and a beautiful opportunity to wear an amazing outfit. When it comes to athletic attire, I believe the shoes are the focal point. If you wear an amazing pair of sneakers with a ratty gym fit… well you’re still wearing a ratty gym fit. But at least your shoes still look amazing. Pair these sneakers with your best Lulu Lemon jacket and you’ve got a look.

What To Wear On A Mid-Day Date For Guys

The Picnic Date

Ahh the lunch date!… now you are sitting down but this time, outside.. and on the ground so attention must be paid to the lower portion of your outfit. These shorts from OAS are ready for the limelight. Pair them with a favorite graphic tee to show off your personality or opt for a nice fitting polo and loafers to jazz it up a bit.

The Fair Date

Amusement parks are notoriously hot and no one wants to deal with the stuffiness of an over the top outfit. So, for that reason we are going to showcase our style in the most practical way possible… shoes! These suede beauties from Noah are in collaboration with Puma and are a classic in their own right. Pair these fresh sneakers with denim shorts and maybe a muscle tee to avoid the farmers tan.

The Museum Date

When it comes to museum dates they are all about sharing thoughts and intellect. Listening to each other’s perspectives and being purveyors of the artist’ work… So what should you guys wear for this first date? Let’s go for a smart look! By smart, I mean smart ass. This graphic tee from Drôle de Monsieur will show off your witty sense of humor perfectly and your charismatic charm will shine brighter than the picture lights on the wall. However, if you really wish to take this look up a notch, tuck your tee into trousers or light wash jeans and finish your look off with sporty trainers. I know.. I know… you can thank me later.

What To Wear For A Date Night For Guys

The Dinner Date

And we’ve arrived. The moment you’ve all been waiting for. The Dinner Date. Now, if you weren’t already aware.. restaurant lighting is horrible. It isn’t flattering in the slightest, and you don’t want to scare your date off with your new third chin. So to combat this undesirable fate, I suggest wearing brighter colors that will bounce light back into your face and accentuate your features. This off-white long sleeve polo from Suit Supply will do just that. Pair it with dress trousers and sneakers for an understated yet refined look. Oh, and one more thing! Don’t spill the wine.

The Casual Drinks Date

When it comes to casual drinks minimal effort is key. Shirt jackets are easy to style because all you really need to do is layer them over a t shirt and put on pants. This Wax London overshirt, could easily pair with the YONY cropped creased pant mentioned previously. Or you could keep it simple and pair it with blue jeans. Another great thing about this top is even in a dimly lit setting your date won’t struggle to find you.

The Theatre Show Date

Theatre shows are a fun way to get to know someone’s interests more intimately. It’s like a movie theatre but better, because they let you to take a break for snacks. But I digress. Even though your feet are sure to be hidden underneath the row in front of you, you must look the part. And let’s be honest, the star of the show is already on stage. For the ones who enjoy live entertainment, I present to you a classic. These chunky penny loafers from Vagabond are sure to become a wardrobe staple. These shoes can transform your white button down and black slacks into something much more trendy and current.

Date night attire is definitely a trick of the trade but it is certainly a skill that can be mastered. By simply finding the pieces that work best for your body type and investing in a few pieces that ring true to your personal style, you’re well on your way to first date success.