Valentines dress fine: Helpful tips for dates and dressing on Valentines day

Hey everyone!

Today I thought I’d give you some idea’s for what to wear on valentines day. 

Want to impress that special someone of yours heres some tips and some idea’s for date spots!


If you want some great visual examples for the clothing options I mention follow my mens fashion on pinterest:


First let’s start with some dating spots because when dressing you always want to dress for the occasion, I could not stress this more. So here are some idea’s I have used in the past and some I thought up recently.


(1) This ones Fer da boyz:

you can never go wrong with a candle lit, home made dinner for 2 at your house. Play some nice romantic music and she’ll be in awe. Not only does it show that you took some time and effort into planing the day for your sweetheart, but allows you to have privacy to be with each other (also make it a surprise, plan this out and have everything before she gets there, the table set, everything ready so when she walks in she’s in shock). Personally I have done this, not even on valentines, and she loved it. 

THOUGH you should still dress up because it is a special night, in this situation I would do something more casual. So take out those chinos, pull out the button up shirt, wrap on that tie, and for a nice touch wear a v neck sweater overtop, this will give you great more casual sophisticated look! 

Colour combinations are endless, I did this today and I wore a navy v-neck sweater, with a lighter blue shirt, I a dark grey tie which matched my dark grey chinos, and black accessories (black dress shoes, belt, watch).

(2) Take her out to a Fancier restaurant, & then a walk in the moonlight. This works really well if you are lucky to be like Windsor and have a skyline like the Detroit skyline across the river. There is a restaurant called the Keg here and it’s right across the street from the river, which works out perfectly for this dating idea. But it doesn’t have to be a skyline, it can be anywhere, maybe where you both met?

In this scenario I would advise dressing a little more dressier, pull out the blazer, again chinos would be the choice, but jeans can work as well, and pick your shirt based off the colour tone of your blazer, again same with the ties, wear a warm coat over top with a scarf, and last but not least, make sure your accessories all match each other. 

In my upcoming blogs I plan to discuss how to match blazers with ties and  suits with ties and discuss the differences in suit jackets, blazers, sport coats etc. 

(3) If you live in a city where its warmer, Id suggest you take her out on a romantic picnic (blanket, food, drinks, the works) at her favourite spot in the city. This like the first of my suggestion, shows you actually planned what you both were going to do, and went an extra length to make it different and special. I have personally never done this because it’s freezing at this time of the year, but if I lived somewhere warmer I definitely would do this. 

In this situation I wouldn’t go full out tie sweater because I’m assuming it would be too hot, so I have two options for this option. First, you could do a classic, wear jeans an untucked button up shirt, tie, and accessories, its casual yet still shows some class. Especially if you don’t usually dress like this. You could also wear a Polo with those jeans, and if its cool enough a sweater, I’d wear a neutral coloured  v-neck, with a brighter more vibrant t-shirt underneath, again still showing that you’re dressing up, but dressed up for the right occasion. 

(4) a romantic spa day of your own 😉

In this situation you would be treating her to a “spa day” pampering and treating her, or maybe you could go to a spa so you both can enjoy the relaxing environment. 

If this was me, there would be one suit I’d be bringing to the date, my b-day suit lol. But if you’re going out to a spa dress casually like in situation 3  & enjoy the time together. Either way do a home cooked (better if your pre cooked this) candle lit dinner. If you really want to go above and beyond, buy her flowers, but unless roses are her favourite type of flowers I would do something not so traditional like Orchid or Tulips.

 (5) My last date idea (with clothing suggestions) is making a marathon of dates. Meaning, go to a different location for each activity. For instance, have a few drinks at her favourite bar, then go to her favourite restaurant for dinner, then go to her favourite dessert place to finish it off before you go back home. This one tho more timely, but it is also a lot more fun and a different date. I want to say thank my friend who gave this idea to me, he says it has worked out great for him! So try it out. 

In this date I would wear something more dressier as well, so this goes back to the chinos, dress shirt, tie, additional sweater and coat if you are in a colder area of the world, and again matching accessories. 

as a side note, although I always mention wearing a tie, with the button up and sweater you can go with no tie and it will look just as classy.

If you are confused about why I keep mentioning “matching accessories” go to my “The Beginning” blog which talks all about it. 

helpful tip NEVER EVER match black with brown accessories and vice versa….. EVER!


just thought I’d add some more idea’s I had while making this blog for dating idea’s (sorry ladies this was more of a mans blog today):

– Ice Skating, bring her flowers and take her ice skating, its a great date, even if you cant skate well (trust me) it just results in her having more fun and laughing. Alternatively for those who are lucky enough not to have ice, take her rollerblading, essentially the same thing. 

– Nothing wrong with a classic; so do a movie date and dinner, there’s so many awesome movies coming out that day it would be a great time, take her to a movie she’s really has been wanting to see. 

– just another tip, be different, outside the box, don’t just get her roses and chocolates like every guy before you has done, or she’s seen in every chick flick, make her feel like she’s in a chick flick.

Well those are my tips on how to dress and where to go for a date this Valentines day! please let me know how it goes and if you liked the tips!

– Mark A. Santoro