Valentine’s Day Date Outfits For Men

You’ve got the perfect date planned and the thoughtful gift picked out, but did you think about what to wear? 

We all know how easy it is to just leave that aspect to the last minute which is why we’re here. Whether you’re planning a candlelit dinner for two or a laid-back hangout with friends, we’ve curated a few outfit ideas that speak volumes without saying a word.

Scenic Walk & Lunch Date

If you planned out the perfect date like going to museums, candlelit dinners, and moonlit lakeside walks, you also might want to make an unspoken effort with your outfit that will seamlessly transition from polished indoors to charming outdoors.

Navy and black create a classic and timeless colour palette, perfect for a romantic occasion. The dark wash jeans and navy polo create a timeless base, while the blue R2 Amsterdam jacket adds a touch of modern flair. The Boss Nadim overcoat completes the look with understated elegance, keeping you warm and confident throughout your date.

Discover more layering tips in our Effortless Transitional Style article!

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Menswearonline Valnetines Day Outfit Idea 1.1

Casually elevated

If you want to keep your date look more casual, but with an elevated twist – adding a contrasting waistcoat is the way to go. 

Jeans, light blue shirt, navy jacket, and camel waistcoat are all classic menswear staples that work well together. They create a timeless and versatile look that’s appropriate for various occasions.

The combination balances casual elements like jeans with elegant pieces like the jacket and waistcoat, creating a smart casual look that’s perfect for a date.

A waistcoat is the secret weapon that elevates an ordinary outfit, adding a touch of gentlemanly flair that’s sure to impress.

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Valentines Day Date Outfit Idea 6

A touch of elegance

Often, when we think of dressing up for a special occasions, we opt for darker colours.

However, if you want to make a statement – a pair of beige chinos and a bold jacket will do all the work for you. 

We love this coral jacket by CANALI. It resonates perfectly with the Valentines theme due to coral unique and romantic colour that is associated with love and passion. 

If coral is a bit too risqué for you, you can opt for a blue jacket, which offers a timeless and sophisticated alternative, perfect for those who prefer a more toned down approach to Valentine’s Day style.

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Menswearonline Valnetines Day Outfit Idea 3.3


If your Valentine’s Day plans include dinner at a fancy restaurant, try this combination of velvet, black shirt, and charcoal trousers.

The velvet jacket adds a touch of luxury and texture, contrasting beautifully with the smooth silkiness of the black shirt and the tailored wool blend of the trousers.

While suited for a classy night out, the chukka boots add a touch of casualness, making the outfit adaptable to different venues and activities creating the perfect balance of classic elegance and modern style.

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Menswearonline Valnetines Day Outfit Idea 2.2


If you planned a casual date after work, we suggest to elevate your existing office outfit with a pop of colour, like a pink jumper.

A pop of colour can instantly transform your work outfit into something date-worthy, especially for a Valentine’s Day outing.

A soft pink crewneck will add a subtle touch of romance while remaining comfortably casual.

This outfit is perfect for a potentially chilly February day as the luxurious blend of wool and cashmere in the BOSS slim fit coat offers both warmth and comfort, while the slim fit adds a modern and polished look.

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Valentines Day Date Outfits Ideas Menswearonline 2.1


Don’t underestimate the monochromatic outfit just because it’s a special occasion. Monochrome (meaning opting for one colour) instantly elevates your look, exuding elegance.

We particularly love this navy shirt by Paul Smith with its playful colourful buttons, which just take this look to the next level.

Don’t forget to check out our comprehensive shirt care guide to ensure your shirt is looking its absolute best for your date!

Adding a white pair of trainers is a great way to inject a touch of personality and keep the look from feeling too formal. It adds a contemporary twist and brings visual interest to the outfit.

Whether it’s rooftop cocktails with your love or laughter with friends, this navy monochrome outfit would be perfect for casual outings. 

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Valentines Day Date Outfits Ideas Menswearonline 1.1 1
Valentines Day Date Outfit Ideas Menswearonline
Valentines Day Date Outfit Ideas Menswearonline 2

Currently studying Business Management and Marketing. Love spending my time at the cafes, trying out new drinks while reading a book.

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