First Date. Look Great.

Hi Santorials!

Do you have a significant other? Do you have a crush? Do you just have a guy or girl you’ve been dying to ask out and finally got that first date?

Here is some of my tips and tricks for dressing for a first date and some idea’s on places to take this girl on a first date. So let’s break this down. Before we even get into dressing for dating or dating spots let’s set some rules! (1) Be yourself! (2) Know the interests of the person you’re taking out! (3) Take my suggestions and modify them to work with the person you are taking/ going with!

Okay; so on a first date there is many places you can go, I like to give them titles. For instance:

The “Classic”

Tiffany M. Blacks WordPress

The Classic is taking a girl/boy out for a dinner and a movie, it’s great for first dates because it avoids the chance of many awkward conversations, having to continue discussions for a long period of time, and depending on the dinner and movie it can be a romantic evening. As for dinner, since it is just a movie and a dinner and it is expected to be more casual, don’t bring date to an upper scale restaurant if you are just going to a movie after.

Now what do you wear on this date?? 

Since it’s a more casual scene wear something in between casual and dressy. For the ladies, some options are wearing a blouse with a lighter denim jacket and darker denim pants or vice versa, a nice turtle neck sweater and some comfortable jeans, or a shall, a tank top, and some nice coloured pants. For da boys, no teared jeans, keep it clean cut. Some suggestions for you are nice dark denim jeans, a button up shirt (tucked in) a casual tie (if you’re feeling extra adventurous try the tie tuck*) and a cardigan, also try some coloured pants and a neutral coloured polo (for example red pants and grey polo), or even nice dark chinos, a button up shirt (untucked) with a tie (don’t tie tuck if you are untucking your shirt) and if you aren’t a tie guy, try throwing on a casual vest and leave it unbuttoned. (layering is important!)

*Tie Tuck: tucking your tie into the second button from the top so your tie is only sticking out about half of what it should.

The “Friends”


This date involves going and grabbing a coffee at a local or chain coffee shop, then taking her on a picnic or ice skating. This shows her/him how special they are and how spontaneous you are, allowing you to have stimulating conversation and a different and romantic night. They will be able to tell how much thought went into this date and how special he/she is (this would even be a great date for people in a relationship as well).

Women: grab your cardigan, turtle neck/ cowl neck sweaters (knitted sweaters are always cute as well), coloured leggings/ jeggings, or jeans with a tee-shirt or blouse to go underneath If its really cold out a toque, scarf and mittens would be a nice touch as well!  This is going to be a more casual nights where you are talking so be comfortable.

As for the men, I’d suggest wearing jeans, a casual sweater (as in cardigan, crew neck, or v-neck)  with a button up shirt underneath or a t-shirt! Get your beanies and toques ready as well, and prepare for a great night! I would do brown accessories and brown pants as well!

The Sophisticated Night Out:

This date would involve going out to an event and a elegant dinner, maybe catching a play or a artistic event, drinking wine and having a nice dinner with great discussion.

So ladies what to wear for this lovely occasion:

I would stick to a nice dress, a shall with some pantyhose, cute flats and some accessories OR wear a pair of Prada’s (the pant not the brand) short heels/or flats (depending on the size of your date) a sweater and a blouse.

Men: keep it sophisticated, nice and classy. Blazer with chinos will be your best friend, ditch the tie at home for this one because you want to look casual not like your going to a meeting.

Hope these tips help if you have any questions or want a suggestion for a specific event you are going to please email me at 

Until next week Santorials!

Stay Fresh,

Mark A. Santoro


Twitter: @MarrkSantoro


Instagram: @Markitfresh