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Valentine’s Day style tips: How men should dress for the perfect date night

Be the best-looking guy at the restaurant on 2/14

Couple watching the sunset together
Mayuk / Shutterstock

One of the biggest nights of the year (if you are lucky enough to be in a relationship) is Valentine’s Day. There are so many of us who find ourselves single on the day everyone celebrates love, but for those of you who are cuffed up this season, your day is right around the corner.

Hopefully, this wasn’t your reminder, but if it was, then you’re welcome. If you did remember and you already have something planned, then you likely have been wondering what you want to wear for your big date. If you haven’t, then here is another reminder: Your date likes you looking your best. Showing effort to make sure they know they are special is a great way to kick off the date night the right way.

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But what should you wear? You don’t want to try too hard, but you also want to make it look like you gave some effort. Here are some Valentine’s Day styling tips to help you strike that perfect balance for the ideal date.

Elevate everything one level

Man in gray tweed and jeans
The Manual

OK, here is the first thing we want you to remember about these styling tips: This isn’t about ignoring who you are. You aren’t trying to be someone else here. Your partner fell for you, so dressing like someone else (someone else entirely, we mean) isn’t the approach you should take. However, taking your typical dress and elevating it slightly is the best way to take what you already usually wear and make it more appropriate for your Valentine’s Day date night. Here are some examples.

  • Outerwear: If you’re the kind of guy who loves a good canvas or workwear jacket, then one easy way to elevate your outfit is to swap out the casual coat with a peacoat or an overcoat. It will be stylish and elevated, and your partner will immediately notice it for a great first impression.
  • Sport coat: If you use the business casual wardrobe at work and go straight to the restaurant, you can easily throw on your best blazer over your work outfit to elevate something from business casual to smart casual.
  • Dress pants: If you are a jeans guy or a chinos guy, you can swap these out for a pair of tailored dress pants, and your entire outfit goes from casual to elevated. Make sure they have that crease down the front so you look terrific.
  • Chelsea boots: Finally, swap your everyday shoes with some Chelsea boots. These are a secret weapon that every guy should have. If you’re wearing jeans, these dress them up. If you are in dress pants, these rise to the occasion.

Choose the right colors

Man in burgundy sweater polo
Mark D. McKee / The Manual

This isn’t a big factor in dressing well for a Valentine’s Day date. But it is a small detail that will pay huge dividends. Being festive when in a social situation makes you immediately more approachable and likable. When you wear red and green around Christmas, people notice. When you don the red, white, and blue on Independence Day, people are drawn to you; it’s a simple lesson in psychology.

Red, pink, and white are the best Valentine’s Day colors, but they aren’t the only ones. Black and gray or blue and brown are always great looks for a date night. But if you are going on an evening date, darken your pink to burgundy and stand out among the crowds. It also shows excellent planning and thought, which is never overlooked.

Subtlety is key

Valentine's Day hat
The Manual

Here is something that so many people get wrong and something that (once you nail it) will always be appreciated by others in your life. A subtle but elevated look does multiple things: it draws their attention to you but diverts it back to them simultaneously.

When you go on a date in something flashy and over the top, it will draw attention, but it will also keep that attention, which makes your partner feel like they get lost among the crowd. They feel like the shadow of your brightness. Remember that celebrating love means celebrating the one you love, not yourself. Keep it elevated, but keep it subtle. Subtle patterns and subdued colors are the best tactics to make someone else feel special.

Don’t just dress the part

Valentine's Day suit
Mark D. McKee / The Manual

This is about style, of course, but style is more than skin-deep. Wearing your clothes well is the best way to make a great first impression, even if it’s only the first impression for the evening and they know you well. But there is also etiquette to keep in mind. This is where your style extends to more than what you wear, but also how you act. Get to the restaurant first, stand when your partner approaches or leaves the table, let them order first, open doors for them, and walk them to their car or subway stop.

Chivalry isn’t dead, but it needs a high level of genuineness to avoid feeling transactional for the other side. If you act the part of the gentleman, then your clothes are more than a costume, but curtains dressing up a beautiful interior. Making your partner feel special on Valentine’s Day begins with what you wear and only goes deeper as the night progresses.

Mark D McKee
Mark is a full-time freelance writer and men's coach. He spent time as a style consultant and bespoke suit salesman before…
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