Ah, the always unnerving ‘what to wear on a date’ scenario. It’s a tough time for a man; trying to blend what makes you feel comfortable with the expected dress code of the venue you’re about enter. That’s without even trying to factor in what she’ll be wearing.

And one particular day of the year becomes the cherry on top of what is already a sundae chock-full of confidence issues, low self-esteem and performance anxiety: good old St. Valentine’s Day.

Now before we get into the meaty part of this sartorial sandwich, I want to clarify two things. Firstly, I appreciate that this article could be excluding a fair amount of our readership i.e. those of you who will be single on this particular day. However, that doesn’t mean it won’t be useful for you in the future or you can’t share past experiences when it comes to dressing for a date. FashionBeans is all about sharing and building each other’s knowledge for future reference.

Secondly, the advice that I’m going to be giving – try not to take everything I say as gospel. I’m going to be providing you with guidance for general situations that could arise but if you happen to be going to a certain place that you already know how to dress for, then go with your gut and dress that way. Don’t follow my advice blindly.

Hopefully, this will eliminate any comments along the lines of “I wouldn’t wear that outfit in that situation…” because if you wouldn’t wear it, then don’t. Simple.

Dressing For A Date – Valentine’s Day

So what do you need to start thinking about when it comes to dressing for a date on Valentine’s Day? Well, you want to make sure that whatever you wear, you feel comfortable. This will ensure that you won’t be focusing on other things such as how uncomfortable and awkward you feel, because this will translate in your body language. This is sound advice for any date really.

More importantly, keep things simple, stupid! You don’t want to be wearing anything too outlandish, outrageous and attention grabbing for two reasons: one, by toning things down and dressing in a simple classic manner it brings your personality to the forefront – you’re a man that’s wearing the clothes, not the other way around. Two, this special day happens to be all about her – so don’t try and show her up, OK?

Other than that, it’s about dressing for the situation:

The Formal Event

Now these are pretty much a rarity but they can happen. If you have somehow managed to wind up in this situation, then check the dress code on the invitation and dress accordingly. It will probably call for minimum a suit, maximum a tuxedo.

Either way, just follow this simple rule: take your trusty navy suit (an item every man should own) and pair it with a closed front French cuff white dress shirt, a black bow tie and a pair of black Oxford shoes.

A foolproof combination for nearly every formal event you could come across.

Key Pieces
  • Asos Slim Fit Suit In NavyAsos Slim Fit Suit In Navy
  • Topman Navy Bogart Slim SuitTopman Navy Bogart Slim Suit
  • Reiss Naples Three Piece Check One Button Suit NavyReiss Naples Three Piece Check One Button Suit Navy
  • Debenhams Black Tie White Long Sleeve Dress ShirtDebenhams Black Tie White Long Sleeve Dress Shirt
  • Burberry Prorsum Cotton Dress Shirt With Pleated BibBurberry Prorsum Cotton Dress Shirt With Pleated Bib
  • Lanvin Dress ShirtLanvin Dress Shirt
  • Asos Cotton Bow TieAsos Cotton Bow Tie
  • Topman Black Textured Bow TieTopman Black Textured Bow Tie
  • Lanvin Woven-silk Bow TieLanvin Woven-silk Bow Tie
  • H By Hudson Burges Oxford ShoesH By Hudson Burges Oxford Shoes
  • Allsaints Merit ShoeAllsaints Merit Shoe
  • Churchs Buckden Leather Oxford ShoesChurchs Buckden Leather Oxford Shoes
The Fancy Date

I.e. one that has required a reservation to be made at least a couple of months in advance. This is normally at a restaurant, with the possibility of heading to a fancy bar for a few drinks after.

In this situation, I would again recommend wearing a suit as it will show you understand the importance of the night. However, don’t dress it like a suit. Skip the belt, the tie and loosen up a couple of buttons.

Opt for a suit with a bit of texture – such as grey tweed, khaki cotton or brown hopsack – in order to cement the off duty aesthetic. Pair them with a simple striped shirt, a colourful pocket square and some burgundy or brown loafers.

Even if you don’t follow this advice to the letter, make sure whatever shoes you wear, they’re in good condition. She will notice, trust me.

Outfit Inspiration

Dressed Down Suits Lookbook

Key Pieces
  • Asos Slim Fit Suit Jacket In TweedAsos Slim Fit Suit Jacket In Tweed
  • Topman Green And Navy Skinny Fleck Two Piece SuitTopman Green And Navy Skinny Fleck Two Piece Suit
  • Reiss Pinot B Two Button Cotton Mixer TaupeReiss Pinot B Two Button Cotton Mixer Taupe
  • Zegna Rossini Fit Bruno Collar Shirt 141986Zegna Rossini Fit Bruno Collar Shirt 141986
  • Reiss Mccaan Striped Shirt Antique RoseReiss Mccaan Striped Shirt Antique Rose
  • Austin Reed Quick Iron Slim-fit Blue Stripe ShirtAustin Reed Quick Iron Slim-fit Blue Stripe Shirt
  • Reiss Gunsmoke Triangular Geo Hank Seafoam BlueReiss Gunsmoke Triangular Geo Hank Seafoam Blue
  • Reiss Braz Lapping Disc Print Hank OrangeReiss Braz Lapping Disc Print Hank Orange
  • Austin Reed Viyella Mosaic Silk Print HankAustin Reed Viyella Mosaic Silk Print Hank
  • Asos Tassel Loafers In LeatherAsos Tassel Loafers In Leather
  • H By Hudson Tyskatu Brown ShoesH By Hudson Tyskatu Brown Shoes
  • American Apparel Logan Shoe By BassAmerican Apparel Logan Shoe By Bass
Drinks & Then A Night Out

This is probably the one scenario where you can really dress however you want, because it will depend heavily on where you’re heading.

Saying that, why not take it up a notch for a change? My go-to here would be a pair of straight slim indigo jeans, an Oxford cloth shirt in blue, white or grey with a complementing cardigan/v-neck jumper. I’d probably top it off with a thin black leather jacket and some black penny loafers. But you could of course substitute in chinos, a t-shirt or a denim/varsity jacket to suit your own style.

If in doubt about colour, stick to neutrals. This is especially true of black and grey because they are always appropriate for evening events, communicate sophistication/elegance and can hide the inevitable stains that come from a night out brilliantly.

This particular look would also be appropriate for a more casual meal.

Example Outfit
  • Farah Vintage Sky Blue Hudson ShirtFarah Vintage Sky Blue Hudson Shirt
  • Farhi By Nicole Farhi Navy Cotton V Neck KnitFarhi By Nicole Farhi Navy Cotton V Neck Knit
  • Reiss Norton Lightweight Leather Biker BlackReiss Norton Lightweight Leather Biker Black
  • Topman Black Italian Leather BeltTopman Black Italian Leather Belt
  • Acne Raw Ace Skinny JeansAcne Raw Ace Skinny Jeans
  • American Apparel Logan Shoe By BassAmerican Apparel Logan Shoe By Bass
Outfit Inspiration

Valentine's Day Night Out Lookbook Inspiration

The Cinema Date

This one’s even easier to dress for, as you’ll spend a lot of the time in the dark anyway.

I would probably still wear a blazer, or at least a smart jacket, as it shows that you want to make the effort. You don’t have to go over the top with a formal version – why not opt for a more casual knitted style or a deconstructed cotton version? Pair it with a neutral t-shirt, a pair of casual chinos and some desert boots.

For those who want to dress down but dress well, try substituting the blazer for a shawl neck cardigan, classic trench or Harrington.

Finally, remember to not be cheap on popcorn and drinks!

Outfit Inspiration

Dressing for a Cinema/Movie Date - Men's Lookbook Inspiration

Key Piece: The Unstructured Blazer
  • Pepe Jeans Casual Blazer Slim FitPepe Jeans Casual Blazer Slim Fit
  • Triple-button BlazerTriple-button Blazer
  • Two-tone Shawl BlazerTwo-tone Shawl Blazer
  • Allsaints Combine BlazerAllsaints Combine Blazer
  • Reiss Fielding Merino Wool Blazer NavyReiss Fielding Merino Wool Blazer Navy
  • Universal Works Navy Poplin Town BlazerUniversal Works Navy Poplin Town Blazer
  • Bottega Veneta Unstructured Slim-fit Washed-cotton JacketBottega Veneta Unstructured Slim-fit Washed-cotton Jacket
  • Lanvin Lightweight Cotton Jacket 141844Lanvin Lightweight Cotton Jacket 141844
  • Dolce & Gabbana Slim-fit Linen And Cotton-blend BlazerDolce & Gabbana Slim-fit Linen And Cotton-blend Blazer
A Night-in/Home Cooked Meal

This could be round yours or hers but either way the dress code is the same – whatever you normally wear there. With the exception of sweats and hoodies, because it’s still a date remember.

You’d probably find me in a pair of dark indigo jeans, a plaid dress shirt and a v-neck jumper, topped off with a pair of leather Jack Purcell’s. But feel free to go with whatever you normally go with.

Final Word

Generally speaking, that’s all there is to it. Just be mindful of where you are going and the sort of expectations your lovely date has and you won’t go wrong.

Then it’s just a matter of relying on your personality to get you through the evening. Which is such a ball ache, right? Why do they think we got into menswear in the first place? So we could snare girls (or guys) with our fancy clothes and not have to worry about things like small talk and being interesting, of course. What other reason could there be?

As always, I want to hear what you have to say – so leave your thoughts in the comment section below. Where are you taking that special someone this year? And what will you be wearing? Do you want to come and see Die Hard 5 with me and all the other sad singles? Let me know.

Matt Allinson