Style Basics

6 ways to dress like a gentleman this Valentine’s Day

By on February 11th, 2015

Valentine’s Day is right around the corner. Whether you like V-day or not, you may as well dress sharp for it. And so this week I compiled a simple list of 6 ways to dress like a gentleman this Valentine’s Day. In fact, these tips are good for the office too.

1. Match your belt to your shoes

I’m starting the list off with an easy one.

If you’re wearing a belt, match it to your shoes. It’s super easy to do and there’s really no excuse for flunking this one. The reason this is important is that a contrasting belt will end up being a distraction as opposed to complementing your shoes.

2. Wear a blazer (or a suit!)

You may or may not be a blazer guy, and that’s perfectly fine. But if you are considering dressing a little more stylish this year for your Valentine’s Day foray, consider wearing a nice blazer. It doesn’t need to be anything too wild; a solid navy or charcoal shade will work just fine for most guys. Wear a neck tie or not, your choice. Maybe a pocket square – wait, scratch that, of course a pocket square!

Regardless, your  significant other will not expect to see you in a jacket if you don’t usually dress in a blazer or suit. They’ll be pleasantly surprised.


3. Buy yourself some decent shoes

Despite studies finding that the first thing people notice when they meet someone new is the shoes they are wearing, most guys are still sporting the same kicks they bought when they landed their first big job. And for a special occasion like Valentine’s Day, the least you can do is wear a decent pair of shoes. That means no scuffs and no worn edges.

If your budget only allows for one pair of nice shoes, then go with black shoes. And with laces. Lace ups will be a little more formal than slip-ons and it’s always a good idea to err on the safe side and be a bit overdressed.

So, go out there and get yourself something that you’ll be proud to wear. If you buy quality, they will last you a long time. And yes, shoes do exist that are as comfortable, if not more so, than the ones you currently own.

To sum up: if you think you need new shoes – you do!

4. Either dress up or dress down, don’t end up in the middle

Whether you lean towards street style or more formal – just don’t mix and match. For instance, please, please don’t wear a button up dress shirt over a T-shirt unless you’re going to actually button it up! You may be going for ‘casually dressed up,’ but instead you’ll look like you had good intentions to begin with and then lost interest halfway through.

5. Put your clothes on and then leave them alone!

In other words, don’t fidget with your dress shirt or neck tie or whatever it is that you don’t normally wear. If you follow any of the tips above, you’ll look just fine.

The best style advice I can give you is to put care into deciding what to wear, and then completely forget about what you’re wearing.

6. Flowers

Ah yes, flowers.

The one thing that arguably never goes out of style for Valentine’s Day.

Let me give you some advice on flowers guys – even if your significant other says that they don’t like flowers because they are just going to whither and die, etc, etc. – they do like flowers. And one thing that I wish I would have realized in my 20s is that being a regular at a flower shop can really pay dividends. It’s a bit of a lost art, but giving flowers, whether it’s on Valentine’s Day or otherwise, is a very thoughtful act.

And don’t think that buying flowers has to break the bank. Yes, a huge bouquet can rival the cost of a fancy dinner out, but a singular flower won’t cost more than a couple of dollars at most – and quite frankly, may mean more to the recipient than 2 dozen.


So, there you have it. Easy ways to look and act more like a gentleman this Valentine’s Day. Adopt some of the tips above and who knows, maybe they will rub off on you the rest of the year! 😉

By the way, here are the items that women wish you would finally toss from your closet.