How To Dress For Your Valentine's Day Date | Men's Health | Men's Health Magazine Australia

How To Dress For Your Valentine’s Day Date

For some couples Valentine’s Day is just another date on the calendar. But for others, especially in their honeymoon period, it’s a chance for both to show their affection. So when you’re organising that special day, what you wear can be the difference between an amazing evening and a horrible nightmare. Your threads will set the tone and she’ll appreciate just how much thought you’ve put into it. 

Picnic Date (park):

If you have the confidence to pull off a date in the park on a picnic blanket, you’re killing it. Bonus points of course for having an (extremely obedient) dog with you! But just because you’ve nailed the food and the scenery, doesn’t mean you’ve hit a perfect score – dress is crucial too. 

With Valentine’s Day falling within the summer months, consider the sweat factor even if it is a night-time event. We recommend a fitted blue t-shirt if you have the build or if you want to go with a more laid-back vibe, a linen shirt. When it comes to pants, chinos and jeans will do favourably.

RELATED: Top 5 Grooming Habits Women Expect In A Relationship

In the footwear department, you have two options really. if you’re opting to go for a laid back skate shoe or boat shoe, we recommend rolling up your pants slightly above the ankle to avoid any crumpling of the pants above the foot-piece. Your other option is a chelsea boot or a Timberland. Boots are perfect because they show you care about the occasion, they fit seamlessly with any pair of pants and they’re also extremely comfortable. 

The finishing piece? Accessories will top off your outfit by shining through your personality – your date will know you’re up for a fun outing straight away. Go with a classic pair of ray-bans or a wide-brim felt hat.



Will and Bear

Will and Bear

Asos Ripped Jeans


Picnic Date (beach):

Picnic dates on the beach are perfect because you don’t have to pay for a romantic backdrop and late at night, the sound of the ocean is soothing. Don’t be afraid to get sandy, you’re date’s in the same boat. If she likes you, she’ll laugh about it. 

We’re really digging a white linen shirt here. Just make sure it’s extremely light to avoid your body over-heating. White linen always looks great with the blue backdrop of the sky and the ocean. Given the beach vibes, we can wear cream coloured pants. When selecting your bottoms of choice, be conscious that the colour is a slightly darker tone than your shirt so you don’t look like you’re in all white.

When it comes to shoes, there are only a few options. Going with the summer ocean theme, boat shoes are perfect. We recommend a dark brown or dark blue shoe that will exude nautical vibes. If you can pull it off, we’re a fan of the leather sandal like a Birkenstock. If they’re your kind of jam, we’re sure she’s seen you in them before so you won’t be scaring her off!

Finish off the look with a pair of sunnies to avoid any potential glare.

Sperry Boat Shoes

The Iconic

Country Road Chino Shorts

Country Road

The Academy Linen Shirt

David Jones


When it comes to restaurant dates on Valentine’s Day, it’s important that you fit in with the vibe of the venue. Do your research. If it’s a local trendy bar, dress smart casual. If it’s formal fine-dining, dress up. Just because it’s a chilled venue, that’s not an excuse to not try – dress to impress – and trust us, she will notice the effort you’re putting in. 

If it is a local eatery, keep it smart casual. In any scenario, just by wearing a nice brand can show you appreciate the significance of the occasion. If you’re well built with desirable arms, wearing a nice t shirt can never go wrong – keep it simple blue, black or white. Be careful that you wear a good fit though. You might be big, but if you’re wearing a size small to show off your arms, you’re in her bad books. Pro tip? You’re not 13, throw away the t shirts that are covered in graphics. Only exception? If they’re from your travels or they’re Mambo classics. – still no reason to pull them out on Valentine’s Day.

For shoes, keep it simple with a chelsea boot or a pair of hush puppies. Again, this will show you’ve put thought into your outfit without going too far. No need for accessories here – you don’t need to cover your eyes from the sun indoors. In the second instant, pick out a formal shoe that’s polished without being too glossy. 

Polo Ralph Lauren David Jones

David Jones

RM Williams The Iconic

The Iconic

Myer Blazer Chinos


Home Cooked meal

Just because you’re in the comfort of your own home, doesn’t mean you can slack off. She has definitely spent more than hour to look her best for you, so you have no excuses to neglect crucial grooming habits. If you put in the effort and play your cards, you might end up under the sheets in the room conveniently next door. (MH Tip: just because you’re in someone’s home, doesn’t mean she’s eager to get down and dirty.)

Perhaps a rare opportunity to wear shorts on a date, a pair of bermudas, short-lengthened chinos or denim shorts will do the job – just make sure they’re tailored.  Couple the bottoms with an oxford collared shirt – preferably a colour to compliment your shirts – think slightly darker tones that blend seamlessly. 

One thing my parents always taught me: if you have guests over in your own home, make sure you’re wearing something on your feet. No one wants to see your toes. Go with a simple staple shoe, it’s causal but the effort to have something below your ankles shows you’ve put thought into the significance of the evening. 

Country Road Blue Oxford Shirt

Country Road

Sullivan Staples

The Iconic

Tom Tailor Denim Shorts


As you prepare for one of the more romantic evenings of the year, just remember that women really do care about what you dress. Not in a superficial way but in a way that says you care enough to make an effort for her. You’re allowed to keep it simple – sometimes style is just the confidence that exudes when you put on a piece of clothing. And remember, always take a jacket. If the evening does go late and there’s a chill coming through, several brownie points for offering her a coat. 

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