How To Dress For Your Valentine’s Date | Men’s health


Picnic date (park):

If you have the confidence to arrange a date in the park on a picnic blanket, you kill him. Bonus points of course for having an (extremely obedient) dog with you! But just because you pulled off the food and the scenery doesn’t mean you hit a perfect score – dress is also crucial.

With Valentine’s Day falling during the summer months, consider the sweat factor even if it is a nighttime event. We recommend a fitted blue t-shirt if you have the build or if you want to go for a more casual atmosphere, a linen shirt. When it comes to pants, chinos and jeans will do the trick.

RELATED: Top 5 Grooming Habits Women Expect In A Relationship

In the shoe department, you really have two options. if you go for a casual skate or boat shoe, we recommend that you pull your pants up slightly above the ankle to prevent wrinkling of the pants above the sole. Your other option is a chelsea boot or a Timberland. The boots are perfect because they show that you care about the occasion, they fit perfectly with any pants and they are also extremely comfortable.

The final piece? Accessories will complement your outfit by making your personality shine – your date will know right away that you are ready for a fun outing. Go with a classic pair of ray-bans or a wide-brimmed felt hat.


Will and Bear

Will and Bear

Asos ripped jeans


Picnic date (beach):

Beach picnic dates are perfect as 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 take to the sand, your date is in the same boat. If she likes you, she will laugh at it.

We’re really digging a white linen shirt here. Just make sure it’s extremely light to keep your body from overheating. White linen always looks great with the blue sky and ocean background. Considering the beach vibe, we may wear cream colored pants. When choosing the bottom of your choice, be aware that the color is slightly darker than your shirt so it doesn’t look like it’s 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 gives off nautical vibes. If you can pull it off, we are fan of the leather sandal like a Birkenstock. If this is your kind of jam, we’re sure she’s seen you in it before, so you won’t scare her!

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

Sperry boat shoes

The Iconic

Country Road chino shorts

Countryside road

The Academy's linen shirt

David jones


When it comes to dining out on Valentine’s Day, it’s important that you adapt to the vibe of the place. Do your research. If this is a trendy local bar, dress smart and casual. If it’s a fancy meal, dress up. Just because it’s a laid back place, that’s no excuse not to try – dress to impress – and trust us, she will notice the effort you put in.

If this is a local restaurant, stay chic and relaxed. Either way, just wearing a nice brand can show that you appreciate the importance of the occasion. If you’re well built with desirable arms, wearing a nice t-shirt can never go wrong – keep it simple in blue, black, or white. Be careful that you are wearing a good fit though. You might be tall, but if you wear a size small to show off your arms, you’re in his bad books. Pro tip? You’re not 13, throw away the graphic t-shirts. One exception? Whether they come from your travels or if they are Mambo classics. – still no reason to take them out on Valentine’s Day.

For the shoes, keep it simple with a chelsea boot or a pair of hush puppies. Again, this will show that you have thought through your outfit without going overboard. No need for any accessories here – you don’t need to shield your eyes from the sun indoors. In the second moment, choose a formal shoe that is waxed without being too shiny.

Polo Ralph Lauren David Jones

David jones

RM Williams The Iconic

The Iconic

Myer blazer chinos


Homemade meal

Just because you are in the comfort of your own home doesn’t mean you can slack off. She’s definitely spent over an hour showing off for you, so there’s no excuse for neglecting crucial grooming habits. If you put in the effort and play your cards, you might find yourself under the sheets in the next room. (MH Tip: Just because you’re at someone’s house doesn’t mean they want to get dirty.)

Perhaps a rare occasion to wear shorts on a date, a pair of Bermuda shorts, cropped chinos, or denim shorts will do – just make sure they fit. Pair the bottom with an oxford collared shirt – preferably a color to complement your shirts – think of slightly darker tones that blend together perfectly.

One thing my parents always taught me: If you have guests in your house, be sure to wear something on your feet. No one wants to see your toes. Go for a simple, basic shoe, it’s causal, but the effort to have something under your ankles shows you’ve thought about the importance of the evening.

Blue Country Road Oxford Shirt

Countryside road

Sullivan Staples

The Iconic

Tom Tailor denim shorts


As you prepare for one of the most romantic nights of the year, remember that women really care about what you dress. Not in a superficial way, but in a way that says you care enough for her to make an effort for her. It’s okay to keep it simple – sometimes style is just the confidence that comes when you put on something. And remember, always take a jacket. If the evening is getting late and it’s cold, several brownie points for giving him a coat.


Comments are closed.