What to Wear on Valentines Day

by Jamie Wilson

Reviewed & updated: October 19, 2022 by Jamie Wilson BA

Need to know what to wear on Valentines Day? Look no further, as this simple style guide will have your Valentines outfit covered for every scenario. 

As the dress-code process can be a walk in the park for women, valentines outfits for guys can leave us slightly puzzled. Whether you have the cliche dinner for two or a spontaneous trip to play some crazy golf, we’ve got the best outfits for guys on the big day.

Valentines Day Outfit Ideas

Valentines Outfit: Evening Meal

If you’re going out for a slap up meal, like most of the nation will be doing, then you’ll want to dress yourself up a little bit to impress your other half. I’m sorry lads, those pizza stained jogging bottoms won’t cut the mustard this time, and I’m pretty sure your other half will be seriously impressed when you turn up looking like Brad Pitt ( a bit of a long shot but we can dream).

When you’re out for a meal in the evening you have to dress appropriately. But appropriately doesn’t always mean bringing out your best suit. If for that matter, a stand-up collar shirt is too unimpressive for the anticipated night, switch to the alternative. A grandad collar shirt is a perfect substitution, which elevates style and looking sharp. Complete the look with a mac jacket and the heritage favourite of a G.H Bass loafer for a classic touch and you are good to go.

Man wearing smart casual in a bar

Valentines Outfit: Cinema

Keeping with the cliche valentines expectations? The cinema will always be a guaranteed successful date destination – especially if the movie is for your own interest rather than theirs. However, if this is your first valentines with a special someone, finding an outfit which doesn’t leave you looking sluggish can be a struggle. Sure, you are probably just going to sitting there for 2 hours, pondering at a movie – however, that doesn’t mean you can get away without making an effort.

For the cinema, you want a look which is relaxed yet effortlessly stylish. Editor’s and I see this as a no-brainer, as we recommend opting for more boxy shapes than to your usual wardrobe. Wide leg chinos are always guaranteed to keep you comfortable yet looking clean-cut. Pair the chinos with a shirt, a pair of converses and a bomber jacket for a full minimalistic look.

Valentines Outfit: Crazy Golf

The tedious activity is always a lot of fun for that anticipated date night. However, this doesn’t mean turning up dressed in your best Tiger Woods gear. Instead, we advise opting for a look which shows a bit of personality but also is adaptable to any crazy golf location. Whether it’s outdoors or indoors, a look which is easy to transition between the two is crucial.

Opting double denim is the first protocol for successfully pulling this look together. While double denim can seem quite spontaneous, it works incredibly well every season. Adding a touch of pattern to your look will also give your look a lift in personality, while also keeping subtle and comfortable. Lastly, to make sure your look is casual down, opt for a pair of minimalistic trainers.

denim jacket striped top mens street style

Valentines Outfit: Day Out

If you aren’t an evening activity type, or both have the benefit of a whole day free – a day out is always the best way to spend valentines with your other half. As it’s February, finding the perfect valentines outfit which keeps you warm but also looking impressive can be a challenge. Fear not, we have the looks up our sleeve the prove it is possible.

A rule to this look is to make sure your jacket is the most tailored piece to your outfit. As you’ll probably be wearing it 80% of the day, make sure it’s the statement piece to keeping your look completely defined. For this, we recommend a spring favourite, the overcoat. Layer with a roll neck jumper creates a modern yet sharp look, without stepping too out the comfort zone.

magic fox mens street style the idle man overcoat peacoat suede

Valentines Day Outfits: Weekend Away

If you feel like treating your other half this year, or, your other half feels like treating you, then you may be off on a weekend away. Lucky you. Of course, you’re going to want an appropriate outfit for travelling in, something comfortable and warm as we always seem to forget that Valentines always hits at the tail end of winter.

When you’re on your way to your fancy new destination you’ll want to be comfortable and practical to any last minute plans at the same time. This means packing tactically. When filling your suitcase, there are some key top picks you must always include which a tailored to any weekend away situation.

herschel weekend bag the idle man

Make sure to pack pieces which shouldn’t leave you looking too overdressed, nor under. We recommend always opting for our own label tweed blazer. Easy to spruce up with a pair of chinos, or comfort-down with a pair of jeans, a tweed blazer will always have you covered. From the ankle down always pack a pair of shoes which are easy to maintain on your trip. Dr Marten’s 3 eye blackout shoes are the blurred line between smart and casual, just like the blazer.

Lastly, an oxford shirt is another ‘last-minute’ life-saver for any crisis you have on your weekend away. The iconic shirt a timeless piece to any wardrobe, or suitcase. Again, easy to wear with almost anything you pull out your suitcase, the Oxford shirt is guaranteed to eliminate the stress.

What to Wear on Valentines Day

  • Suited & booted will always a spot-on choice for most evening occasions on the day.
  • If your partner can’t decide where to go, casual with a smart blazer can also suit every scenario.
  • Always add a touch of personality with colour and statement pieces.
  • Opt for more slim-fits in your looks.

mens street style beige blazer

On That Note

It doesn’t matter what you’re doing for Valentines Day, just make sure that you look stylish whilst you’re doing it. Your other half will be impressed, trust me. Whether you’re off for a weekend away or going out for an evening meal, you can always look smart and stylish.

Following this guide will refrain you from last minute dress-codes and guarantee to looking prim and proper for the day (or night). Howeve\r, if your plans are still up in the air, you cannot go wrong with a casual-smart blazer and a pair of jeans. Going between smart and casual will have you covered for whatever the scenario – and will leave your other half impressed.

Feature image from Pinterest

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