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The Last Word

A Valentine's Outfit

Valentine’s Day can be a high pressure time of year, with the impetus to get the card, present, activity and flowers right getting many men hot under the collar. This is before you even the navigate the sometimes tricky world of selecting your outfit.

Whether you’ve been with your partner for a while only you’ve only got together recently, you want to look your best for this special day. To help we’ve pulled together four outfits that will cover you no matter where the day takes you.


The cinema is a classic Valentine’s Day date venue, with plenty of viable options to see this year including the likes of T2 Trainspotting, La La Land and Jackie. As you’ll be obscured in darkness for most of the evening, turning up dressed to the nines is probably inappropriate. Instead, a focus on casual comfort is the way to go, stopping short of stepping out in your pyjamas, of course.

The classic Harrington, black jeans, t-shirt and trainer combo, supplemented by a Portobello watch, is your perfect option

Slightly Formal

By trading in the cinema for a decent local restaurant with a Valentine’s menu on, the level of formality ramps up a notch, too. Trainers are the first thing to go, swapped out for a pair of classic brogues, while the black jeans that worked at the cinema are also inappropriate here, with cotton trousers in a light marl, teamed with a textured crew neck jumper and blazer, the perfect option.

The day/date display on our Ben Sherman watch adds an extra veneer of class, and shows you mean business.

Smart Casual

Between the two, is the much-maligned smart casual. It’s negative reputation seems unfair to us, although there is no denying the phrase has caused much confusion when it’s appeared on office party invites over the years.

Despite all of this, it’s not at all difficult to pull off the smart casual look, perfect for if you’re cooking a meal at home or if you’re getting a quick bite to eat before hitting the cinema or a bar.

A parka is a great choice here, with its classic sensibilities counterbalancing nicely with the playfulness of the fishtail. The desert boot is the ultimate smart casual footwear of choice, and our Portobello striped watch juxtaposes well with the chequerboard shirt.

Dressed Up

You’ve gone all out and booked into a Michelin starred restaurant, or that place run by that bloke of the telly. You haven’t skimped on the venue, so don’t skimp on the outfit either.

Opt for a gingham-checked shirt – a Ben Sherman staple – teamed with our stretch skinny chinos. The embossed-strap version of our Portobello adds welcome texture to the outfit, with the clean lines of our cotton mac finishing the outfit off in style

Watches play a big part in each of our outfits – you don’t want to be late for the night you’ve planned meticulously after all – and we’re giving away a Ben Sherman watch of your choice up to the value of £85 to five lucky winners. Simply visit this page to put your name in the hat.