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A Typical Scene on Valentine's Day

Styling Outfits For Valentine's: A Guide For Men

Have a date for Valentine's? Congratulations signore! We wish you the best of luck! But have you thought about what you're going to wear?

This is your chance to make a great impression and to show off your best qualities, including your superior fashion taste, so it's not something to take lightly.

Your appearance will speak volumes before the two of you even have a chance to exchange a word, so make sure you take special care and attention to your outfit!

A special day requires special care and attention devoted to your look, but it's always best to know the occasion. Tailor your outfit to suit the kind of date you think you'll be going on. If you're unsure how you should wear your outfit to a particular venue, feel free to take our advice with these simple tips. 

To get the very most out of your apparel, check out our style guide!

Valentine's Day Couple

Styling For A Dinner Date

If your destination is a fancy, upscale restaurant, you want to make sure that your outfit reflects the proper level of sophistication, but don't go overboard.

The key here is to look refined without actually looking like you're trying to look refined.

Try not to dress like you would for a job interview or for a business interaction; you want to look sharp, but not reserved or like a businessman, don't be stilted in your appearance. Be calm and casual, but keep your profile sharp and debonair. 

Here you can opt for a blazer or suit jacket, worn smartly with no tie. Use a darker color palette (navy or black are classic options) and remember to wear a quality dress shirt underneath your jacket. Depending on your desired level of formality, experiment with crew neck and collared shirts until you find one that suits your outfit.

Take off any coats you have on when you sit down, but remember to leave your blazer on while dining.

Black Suit And White Dress Shirt

Make sure your undershirt is crisp, neat, and properly matches the rest of your outfit. Crew neck undershirts are great for creating a very modern, streamlined look, while collared undershirts are more traditional and classic.

For a more modern look, or if you think you might be in cold weather during your date, you can sport a sweater in lieu of a dress shirt.

Styling a blazer or jacket with a sweater might creates a slightly more modern look than with a classic button-up dress shirt, and it can look great when worn correctly.


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Combine whatever top you decide on with a nice (darkly colored) set of dress pants, dark denim jeans or a pair of chinos. 

Complete your look with a pair of brogues or plainly styled dress shoes. Oxfords are the epitome of the classic option, are very versatile, and can be paired with modern and vintage looks alike.

For the highest level of formality for your footwear, try a pair of monk straps styled with crisp, clean socks. 

Styling For A Day Date

This situation is a bit easier to style for, and calls for more casual styles, but you should still consider what you're going to wear carefully. In this situation you'd be going to places like the movies, bowling alley, the park, a café, and etc.

The key for styling for a date out on the town comes down to one thing: versatility.

Since you'll be moving around a lot, going between indoors and outdoors, and doing physical activities, you'll want to dress in light, comfortable layers that can easily be taken on or off to suit the moment. You'll also want to portray a slightly more casual style than you would at a high-end restaurant.

Leather Jacket And Crew Neck Casual

Dark denim pants with a sweater and leather jacket all pair well with a clean, crisp pair of sneakers, but if you feel like rocking a slightly more chic look, pair them with a pair of Chelsea boots.

Chelsea boots are a great, casual option that look great with a variety of styles and are durable enough to be worn outdoors.

Chelsea boots styled with dark denim jeans

Unless you've opted for a very formal style, stay away from more vintage style dress shoes like Oxfords, since they don't pair as well with more casual outfits.

If Chelsea boots are too formal and sneakers too casual, try a sleek, modern styled loafer. Loafers can be worn with casual and semi-casual styles and can feature sleek, modern designs.

Remember: Fragrance

It may seem obvious, but many men forget the importance of fragrance when determining their overall look. But a true gentleman knows that how you smell is going to be just as important as how you look and how well your attire is styled for your occasion.

Like we mentioned in our previous post, menswear and fragrance go hand-in-hand, and anyone truly interested in presented a well groomed appearance is going to want to pay attention to the connection between the two.

Cologne Application

So please, don't neglect how you smell. It would be a shame to style your outfit well only to find that your date thinks you smell bad.

Since scent is so closely linked to memory, even more so than a properly styled outfit, a well chosen fragrance is going to be highly memorable, and the memory is going to stick with your date long after you two part ways.

In short, fragrance, along with your initial appearance, will set the tone for the entire outing.

Valentine's Couple

 Apart from creating a pleasant experience for your date, certain fragrance types can instill confidence and focus in their wearer, creating an aromatherapy-like effect. Take advantage of this fact to gain that slight psychological edge and confidence during your date. Every little bit helps!

Good luck! Al cuore non si comanda!

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