What to Wear for Valentine’s Day


Valentines Day Date

Style Edits for Dates in 2020

Valentine’s Day, it takes us by surprise every year! We have only just recovered from Christmas and New Year and suddenly the big V is on the horizon!

Whether you have someone special in your life to celebrate with, or you treat it as a day to show big love for your fellow singletons, Valentine’s Day need not be a last minute panic for gifts/outfits/something to do.

It’s easy to leave the outfit part of Valentine’s until the last minute, but V-day can feel as daunting as receiving a ‘smart-casual’ invitation to any event. You probably won’t want to show up to your date in a full tuxedo with a rose between your teeth and comically sized heart-shaped box of chocolates under your arm. Equally, this is not the day you want to show up in your ‘fancy’ joggers with a birthday card from the garage that you have crossed out ‘Birthday’ and replaced with ‘Valentine's day’ and a KitKat with a reduced sticker on!

If you’re keeping it low-key casual with a quiet drink or an ever-romantic Netflix/takeaway combination, frankly, we don’t blame you. You can still make an effort with what you’re wearing on Valentine’s Day. Week old lounge joggers and your paint splattered hoodie just won't cut it! Whether it's a ‘mate date’, your first date or your hundredth date, a little thought can go a long way to making sure you look dapper and feel confident this Valentine’s Day.

The Henley House has your back! Stick with us and we will give you some ideas for fun dates and style edits for each!

Let's begin with a classic…

Dinner Date

Fancy Dinner for two at Cheal's of Henley - Henley-in-Arden

Cheals of Henley

You can’t fail to impress with a fine dining experience on Valentine’s Day and Cheal's of Henley is an outstanding example of incredible cuisine mixed with a wonderful atmosphere. Chef Director and restaurant co-owner, Matt Cheal is part of the reason why Cheal's is the go-to restaurant in the area! Not only are Matt and his team ridiculously talented, but they are dedicated to locally and seasonally sourced ingredients with specialisms including meat and game as well as a beautiful array of veg grown on the nearby Cheal’s allotment.

Cheal's of Henley has 40 covers in the restaurant so there's a buzz about the place but it's not overcrowded - perfect for an intimate dining experience. This is one of our favourite places to visit for special occasions and the eagle-eyed among you will notice the front of house team sporting some very fine tailoring...wonder who styled them! So with the wait staff looking debonair, you will want to dress to impress!

Don’t confuse going all-out with overdoing it. All-out to The Henley House, is a polished version of yourself in classic tailoring. For somewhere like Cheal's of Henley, or any fine dining establishment really, you have full licence to go fully suited and booted in a three piece suit or take it down a notch with a two piece or a mix and match look. For a Valentine’s Day fancy dinner, jeans should really be avoided. Instead, build a look around elements of tailoring whether that's a full suit, mix and match trousers and jackets or a more laid back trouser and shirt combo. Remember, you’re not off to a job interview so, loosen it up. Try separates in complementary colours, subtle patterns or a dressed-down double-breasted jacket.

If casual is more your speed, don't be afraid to ditch the tie. You can still look polished and put together with an open collar and blazer look, plus you reduce the risk of dipping your tie in the wildly delicious Mussel and Saffron soup! For something a little different, why not play with pattern and texture? Add a touch of personality with accessories like a pocket square or cufflinks. Cheal's of Henley has a relaxed atmosphere oozing with class and sophistication - much like its menu - so you can have fun with your look for the evening without putting out the nose of the concierge! Chances are, every bloke in the place will be wearing a shirt and tie (it's a go-to classic after all) so for stand out elegance why not swap out the shirt and tie for a turtleneck or a lightweight knit.

Date Night Edit:


Burgundy three piece suit

Burgundy Three Piece Suit - £349.00

Black Silk Pocket Square - £15.00

Baker Tunstall Double Monkstrap Shoe - £225.00

Remus Uomo White Detailed Shirt - £65.00

Burgundy Swirl Blazer - £179.00

With the stunning three piece Burgundy suit as your foundation you can really play with this loo. Try wearing it as god intended with an open collar white shirt and pocket square or ditch the waistcoat and show off that crisp white shirt. Why not swap out the jacket for this gorgeous navy and burgundy one for something a little different? We are obsessed with the effortlessly cool monk strap shoe at the moment and this double buckle version in black would look banging with this outfit ... so many options

Wild Date

Ghetto Golf and Cocktails - Digbeth

Ghetto Golf Birmingham

Demonstrate your sporting prowess and get flirty with a cheeky bit of competition at Ghetto Golf in Digbeth. For a date with a difference why not go a bit ghetto! The best thing about Ghetto Golf in Digbeth is that it is also a cocktail bar so it is strictly 18's and over so your date won't be interrupted by the spunky 7 year old taking 40 attempts at the first hole. With rounds taking between 60 and 90 minutes to complete and packages starting from £10 per person, Ghetto Golf doesn't have to break the bank!

Don’t be fooled though…this is not your average crazy golf, Ghetto golf is a seriously twisted 18 hole mini golf course surrounded by incredible street art and DJ's pumping in the party vibes.

Worked up a hunger? Treat your date to some insanely tasty BBQ street food at the brilliantly named ‘Apocalypse Cow’ and then chat the night away at the ‘Birdie Bar’ with cocktails sure to get you just as twisted at the gold course itself! (Don't forget to drink responsibly and never drink and drive - and all that jazz!).

The venue has a smart/casual dress code so active-wear and joggers will have you turned away at the door. There are lockers available, so beat the chill with layers safe in the knowledge that you can store away your gear safely whilst getting your date on! No-one wants to be the Donkey carrying all the coats and scarfs from hole to hole!

A fun date needs a strong look, don't neglect the basics of dark denim, a striking white T and a painfully cool jacket to pull it all together.

Date Night Edit

leather jacket

Remus Uomo Black Leather Jacket - £139.00

White Round Neck T-Shirt - £20.00

Black Pursuit Trainer - £40.00

Remus Uomo Black Aldo Chino - £69.00

Athos Black Jeans - £79.00

Bristol Black Chelsea Boot - £54.99

V Neck Merino Wool Khaki Fine Knit Sweater - £55.00

You can't go wrong with a leather jacket, and this bomber style is a modern take on the moto style we see a lot of. Keep your lines clean with a basic white T and black jeans or chinos and a leather trainer or add a pop of colour with this khaki merino wool sweater. For a more industrial feel, add these black Chelsea boots and take your look to the edge!

Chilled Date

Dinner and Drinks at The Boathouse - Stratford-Upon-Avon

The Boathouse Stratford upon Avon

Want to wow your date with fantastic food and a great atmosphere, but don’t want to go the full ‘fancy dinner’ route? The Boathouse in Stratford-Upon-Avon is the perfect balance of feeling luxurious and special without being over the top ‘fancy’. With new owners, a brand new menu and a complete face-lift, The Boathouse is fast becoming the ‘place to be’ in Stratford-upon-Avon.

The Boathouse is an independently owned riverside bistro and bar offering freshly prepared food in a friendly and relaxed environment. The Restaurant has the best views of the river which, quite frankly, looks magical at night. The restaurant is situated on the first floor of an 18th Century working boathouse...super romantic! The menu at the Boathouse is really varied so you and your date will be spoilt for choice - the burgers are bangin’, for the record! What’s even better is that you won’t be left tripping over your tongue trying to pronounce the names of the dishes.

One thing The Henley House loves about The Boathouse is the way it seamlessly incorporates the restaurant and bar into the same space, you get the relaxed feeling of being at a restaurant then only a few steps later you get the atmosphere of being at a great bar!

For a Valentine's Day date at The Boathouse anything goes, to an extent, but smart casual attire should be your go-to. When in doubt, combine some of your favorite casual basics with tailored pieces such as chinos and a blazer or even jeans paired with a waistcoat. Taking a piece of striking tailoring can work wonders for taking an ‘okay’ outfit to a whole other level.

Why not jump in on the theme of The Boathouse and add a nod to the nautical look? Think chinos and loafers with a shirt and blazer or fine knitwear - just leave the captains hat at home, trust us on this one!

Date Night Edit

Barker Studland Loafer in Castagina Suede - £225.00

V Neck Merino Wool Cabernet Fine Knit Sweater - £55.00

Remus Uomo Indigo Jeans - £79.00

Cavani Bonito Cropped Suit Trouser - £65.00

Penny Round Collar Shirt - £35.00

Marl Grey Coat

Marl Grey Overcoat - £220

We love these gorgeous, rich brown loafers, wear them with no socks and show off a bit of ankle! With these uber stylish shoes creating the base for your look, go bold with these checked cropped suit trousers or add a casual element with these indigo jeans which can be styled with a turn-up or worn as they are. Add a touch of flare with the penny round collar which is very on trend for 2020 or switch it out for a nod to Valentine's day with a Cabernet red merino wool fine knit. For that romantic stroll down the river after dinner, you can't go wrong with this sleek and stylish marl grey overcoat which looks good with anything - also available in other colours if you prefer a darker tone. Rock the boat with a bold look this Valentine's Day!

Luxurious Date

Spa Day or Stay at The Belfry - Wishaw

The Belfry


Experience total relaxation at The Belfry Spa, this is the perfect place for a luxurious retreat located just outside of Birmingham. For a Valentine’s Day full of peace and pampering, The Belfry is an opulent hotel and resort offering indulgent spa day and spa break packages sure to get you major brownie points.

Enjoy the pleasures of the modern man with the Fire and Ice Spa, which is an invigorating 90 minute relaxation experience through a variety of bio thermal rooms or make use of the world class spa and fitness facilities by creating your own package.

It would be remiss not to mention that the Belfry is synonymous with golf and has hosted the Ryder Cup four times – more than any other venue in the world. So, why not treat you and your date to a Golf stay at The Belfry and combine the serenity of a spa break with the thrill of some of the best golfing in the area!

For Valentine’s Day you could treat yourself to the incredible 5 course tasting menu at The Ryder Grill for just £70 per couple, and really indulge in a weekend of delights! The Belfry is in idyllic settings and boasts the ultimate in modern luxury across the hotel, spa and resort as a whole!

A little planning will ensure you are looking your best, whether you are lounging in the pool or propping up the bar! Don’t forget your swim shorts!

Packing light is key, so make sure elements of your outfit can take you from day to night!

Date Night Edit



Black 3 Button Polo Remus Uomo - £75.00

Bella Blue Cavani Jacket - £90.00

Grey Textured Checked Jacket - £179.00

Black Cavani Halifax Side Zip Boot £54.99

Remus Uomo Black Aldo Chino - £69.00

Athos Black Jeans - £79.00

Cross & Jones Luxury Swim Shorts - £35.00

You may think we have gone a bit mad by suggesting this long sleeved three button polo as our core piece for this look but it can be paired with swim shorts for a casual daytime look to take you from breakfast straight to the spa then worn with both casual and smarter looks throughout the weekend. Worn with black jeans and the incredible side zip boots, it creates a sleek silhouette for an elevated casual daytime look for that spot of lunch. Switch out the jeans in the evening for black chinos and a blazer for the perfect smart casual look for a romantic evening dinner. Go bold in blue or add some fun with the grey checked jacket for a modern take on smart casual.

Casual Date

Day out at the Black Country Living Museum - Dudley

The Black Country Living Museum

Why not shake things up and think outside the box this Valentine’s Day by taking a visit to the Black Country Living Museum. Stay with me here ...The Black Country Museum is not the stuffy, cruddy museums you got dragged around on school trips, it’s an immersive experience and the location for many scenes in Peaky Blinders!

Why not show your cultured side and take your valentine on a day date, get hot under the collar at the brass foundry or take a romantic stroll around the boat dock and thrill your beau with your best Tommy Shelby impression! Walk in the footsteps of the whole Shelby gang at the Black Country Museum, what could be more romantic than standing under the Canal Street Bridge which became the secret meeting place of Ada and Freddie. So don your best tweet and make an impression!

Get gastro with some old timey fish and chips washed down with a pint of traditional local ale at the Bottle & Glass inn. Everything you could want for a day date is within easy reach at the Black Country Museum and with Birmingham City Center just 30 minutes drive away, the day doesn’t need to end when the museum closes! With one of the most vibrant night lives outside of London, Birmingham has everything from cozy pub nooks to snuggle into, to epic club nights at venues such at Lab11, PRYZM and The Tunnels.

Whether or not your date continues into the night, chances are you will spend the day moving between the indoors and outdoors. So, as well as thinking about looking good you will need to be savvy with layering and ensure that you’re prepared for every kind of weather that February can throw at you. Try teaming stylish outerwear with a mid-weight piece of knitwear, classic crew neck T and pair of dark indigo jeans, or mixing elements of your Peaky inspired tweed suit with classic denim and sturdy boots.

This brings me nicely on to footwear, you’ll want to go for a style that’s both sturdy and comfortable – boots (whether a classic chelsea boot or more industrial style) and leather trainers great options here.

We’re not promising anything, but if the combination of the bracing fresh air and a touch of tweed mixed with a cosy pub corner or a stroll down the canals doesn’t create a 'romantic environment', then we’re not sure what will!

Date Night Edit

Cavani  Blue Windowpane Check Tweed 3 Piece Suit - £169.00

Brendan Check Wine Brown Tweed Suit - £159.00


Penny Round Collar Shirt - £35.00

Drake Navy Overcoat - £189.00

Remus Uomo Indigo Jeans - £79.00

Cavani Holmes Signature Lace Up Boot - £79.00

Navy Mock Turtle Neck Jumper - £75.00

We have doubled the fun with this edit, for your foundation piece a three piece tweed suit is the way forward. We love both of these suits, the blue tweed is a little more sleek and fresh whereas the reddish-brown tweed has a gorgeous texture and warmth. With both of these suits you could totally go all out and wear them as the three piece looks but chances are if your Valentine is 'in' on the location of the date chances are they will be a little more dressed down - therefore we would suggest a deconstructed look. We love the way tweed works so beautifully with denim, so why not go for the indigo jeans styled with the penny round collar shirt topped off with the waistcoat and jacket of the suit? Or even ditch the waistcoat altogether! Another option would be to wear the suit trousers with a cosy mock turtleneck fine knit sweater layered with this timeless navy overcoat. Every combination of this look will be pulled together by the Cavani Holmes Signature Lace Up Boot, which we totally rate for both style and comfort! Keep the nods to Peaky Blinders on the subtle side with beautiful tailored tweed.

Final Thoughts:

Whatever your plans are for Valentine’s Day, and whoever you will spend it with, look fly and feel confident with The Henley House as your ultimate wingman! 

Valentine’s Day can feel like a lot of pressure...pressure to arrange the best date, to buy the best gift and to be your best self. Modern life is filled with so much pressure, so take a load off your mind and let us help you find your style for your Valentine’s date.