Peter’s Guide to Dressing for a Date

Ah, Valentine’s Day. I remember our 2nd Grade class getting loads of pink cardboard paper and glitter to create cards for “our valentine,” not knowing what that was. Then I found out. A good way to jump-start anxiety at an early age. Fortunately, I was exempt, because if you’re like me (you know who you are), every day is Valentine’s Day!

But let’s say you want to take your SO on a special date. What do you wear? The answer to that depends on the situation. Dinner and a movie? Opera and cocktails? A walk on a moonlit beach? Decisions, decisions.

The quick answer is: be you, but a bit nicer looking. You could show up in your pajamas, but dressing up demonstrates respect for your date and the occasion, because both are special, right? Right. Unless the date is a pajama party. In which case, wash your pj’s first.



For new couples, keep it casual. If you’re meeting at a coffee shop, wear a nice pair of jeans or khakis, a button up oxford, and clean sneakers or oxfords. After coffee, why not take a walk at a nearby park? Or better yet, find out what activities she likes – hiking, bicycling, karaoke – and plan around that.

valentine's day outfit menswear

Shawl collar jacket: Eidos | Long-sleeved t-shirt: Orcival

Of course, just because you’re a new couple doesn’t mean you can’t get all fancy. If you’re date’s down for a night on the town, go for it – and dress accordingly. If you start with dinner at a nice restaurant, go for a dark outfit. It’s safe, unfussy, and easy to dress up or down, depending on where you go. A fail-safe option is a navy suit. Pair it with a crisp white button up shirt, or swap the shirt for a thin charcoal or black merino turtleneck. If dark jeans are your thing, reach for black Chelseas or zip boots, a blue oxford button down, and a grey tweed sport coat or field jacket.

Daytime date from Beige Habileur. Everything about this is awesome and chill, but refined.

Shirt: G. Inglese x Beige | Pants: Husbands



Perhaps you’ve been together for a while now, and are looking for something special to do. Show that you were paying attention – you were, weren’t you? – by choosing something she said she liked to do. It could be a picnic, wine tasting, or a leisurely walk to a park, downtown, or movie theater. If you have access to a beach, lake, or river, walk there, and bring a frisbee with you to enjoy the sun – everybody can play frisbee. All you need are a nice pair of jeans, boots, and a nice button-up shirt.

However, when it’s a special occasion that calls for something a bit more formal, consider what she’ll be wearing. Being over- or underdressed can be a bit embarrassing, so set the tone by saying “Let’s dress up,” and be sure to follow by saying what you’re wearing so that she can have something on which to base her decision. On the other hand, she could have that one outfit that she’s been dying to wear, so let her choose and follow suit. What if she says she has nothing to wear? Besides starting an argument (don’t do it), you have two options: go shopping with her (that’ll score you major points) or tell her far enough in advance so she can plan to go shopping with friends. Whatever she chooses, be a gentleman and let her take center stage. You may have the perfect red velvet cocktail jacket, but be careful not to outshine your date; remember that this is her night. Show that she’s important by taking her into consideration. For example, ask her what her favorite outfit of yours is and wear it. Or find out what her favorite color is, or which one she’ll be wearing, and chose a flower or pocket square that complements it.

the armoury menswear outfit date night valentine's day

Shirt: The Armoury | Pocket Square: Drake’s


Dinner and a show is always a safe bet, but why not try something different? Go to that one restaurant she’s been dying to try, and then follow up with a dancing class. Or you could go to a club that plays her favorite music. Many museums have evening hours, perfect for an after-dinner stroll and providing easy topics for conversation. If black tie is too formal, a nice suit, comfortable shoes, and a listening ear are all you need to enjoy your time together.

Pro tip: if she likes perfumes, start the evening out by going to a department store and trying scents. Let her pick one for herself, ask her to pick one for you, drop your bank card, and the rest of the evening is set. You’re welcome.

Evening date - houndstooth flannel suit and rollneck

Evening date – houndstooth flannel suit and rollneck.



Grey flannel suit: Eidos
Navy turtleneck sweater: Stephen Schneider


Any date, no matter the day, is an opportunity to show your partner that you care about your relationship. Let your dress reflect that by notching it up a bit. These are occasions to engage in relaxed conversation, have fun, and cement your relationship. The special dates are your chances to create long-lasting memories. Don’t let your dirty sneakers ruin it.

Top 10 Valentine’s Day Netflix Binges

Valentine’s Day sucks.  Now, I’m not saying that you shouldn’t celebrate your undying love, nor even to not celebrate Valentine’s Day at all.  However, the day itself sucks.  It’s a money grab, and every even peripherally-related industry knows it.  Roses are about four times the price of roses the day before or the day after, and restaurants change their menus to hackneyed Valentine’s Day menus that are designed to be able to be easy to prep and serve.  Every chef I know hates the Valentine’s Day menu.  None of them want to cook yet another molten chocolate cake.  Do you really want to eat food that is cooked with that degree of hate?

No, of course not.   Choose love, choose life.  Choose to stay in and netflix and chill.  Literally.  Here’s my list of the top 10 Valentine’s Day Netflix binges.  Your date night can wait until the 15th.

  1. Daredevil (Netflix)Starring that guy from Numbers, and also Hannibal (Charlie Cox), the first and second seasons of this adaptation of Marvel’s blind ninja-like superhero mixes complex characters with a somewhat convoluted, but still generally compelling, narrative.  It also features some of the best fight scenes since, well, Old Boy, which inspires single take fight scene in a hallways full of henchmen.  The Valentine’s Day tie-in: the muddled relationships between the main characters.
  2. Orange is the New Black (Netflix)

    This adaptation of Piper Kerman’s novel is a bit less gritty than the memoir, and a lot less “authentic,” but that goes for pretty much any adaptation.  No one really wants a police procedural in which a moose wandering in the park is the main crisis, anyway.  The later seasons get a bit flabby, and then bam, you are hit with a doozy of a season.  Of course, in the memoir, the protagonist is in the system for two years.  So, to fill out so many episodes, either she has to get stuck in the clank for much longer, or things just happen at a frenetic pace in prison.  Romance?  It’s a choice between Jason Biggs and Laura Prepon.  C’mon now.  Of course, then you get a season of Ruby Rose.
  3. The Walking Dead (AMC)The Hospital Scene in the very first episode of the series, when Rick wakes up from coma into a world that has taken a decided change for the worse, still resonates.  It’s hard to describe the awesomeness that is the first two seasons, and “survivors navigate lawless, zombie-ridden America” seems somehow inadequate to describe one of the best shows of the decade.  Enjoy  the first two seasons as our protagonists navigate couples counseling in the zombie apocalypse.
  4. Lemony Snicket’s A Series of Unfortunate Events (Netflix)This was much anticipated, and it doesn’t disappoint.  At least, not the first few episodes.  No spoilers, please (my kids finished this one well before me). The show follows the three talented and precocious Baudelaire children, who constantly outsmart the villainous, vain, and only semi-competent Count Olaf, who is after their vast fortune following a mysterious house fire that apparently claims the lives of their parents.  The series plays out like a collaboration between Wes Anderson and Tim Burton, and it’s really an excuse – I mean vehicle – for Neil Patrick Harris to ham it up.  And there is nothing wrong with that.
  5. Narcos (Netflix)I thought I was practicing my Spanish, but it seems that the joke is on me. Apparently, Wagner Moura, who plays Columbian drug kingpin Pablo Escobar, speaks terrible Spanish. Nonetheless, he gives an amazing performance that is charismatic and terrifying, and sometimes, touching.  Besides, the series is visually stunning.  The entire show drips the heat and the fecundity of jungles and blood, although I think that the setting never moves further north than Miami).
  6. Black Mirror This is the American release of a British anthology set in a dystopian near-future (or even a future-now).  That it’s an anthology means that unlike the other, character-driven series I’ve been recommending, it will be easier to stop watching so that you can get to more Valentine-y activities.  Note: if you are looking to engage in after-the-show intimacies, maybe skip the pig-fornicating (really) episode.  Unless you like that type of stuff.
  7. Justified (FX, on Amazon Prime – I know, I know)If ever there was an American hero, it would be Timothy Oliphant’s Raylan Givens.  That is to say, he embodies being crap at relationships while being hyper-competent at his job, which he demonstrates by acting constantly insubordinate in the name of efficacy and efficiency.  In other words, he sucks at relationships, but that’s okay because he is a badass who gets things done and is a rugged individualist who has no time for bureaucracy.  Also, he is great with one-liners.  If you have ever dreamed of being this hardcore even once, this show is for you.
  8. Shameless (Showtime)Robert H. Macy plays the drunken, narcissistic, father of a large Irish family in South Chicago.  The family copes with the turd pie life serves to them, as well with all the romantic, legal, and other mad troubles they get themselves into.  What’s to not like?  It’s like your family, but with much better acting.  Plus, you have Emmy Rossum as Fiona, the oldest sibling.  The show is worth showing for that alone.
  9. The Leftovers (HBO – on Amazon Prime)What if 2% of the population of the world suddenly disappeared?  The Leftovers explores the world after something that could be the rapture.  On Valentine’s Day, a day dedicated to love, counteract all those gooey, icky feelings with a marathon spent watching of a show dedicated to the themes of isolation, grief, and disorientation.
  10. Westworld (HBO – on Amazon Prime)In Westworld, androids called “hosts” cater to the whims of the paying customers, or “guests,” in a virtual western setting.  But what happens when the hosts start to realize that maybe not everything is as it seems?  You can see this as a treatise on artificial intelligence.  Or, it could just be a fun and scary science fiction show.   This was one of the HBO’s biggest names of 2016, and for good reason.

    Valentine's Day Netflix

There you go.  Hours and hours of passive consumption.  After all of that, you should have at least some energy left.  Enjoy yourself.

3 Valentine’s Day Cocktails

Visit a bar and meet someone. Go out on a date and enjoy yourselves. Have a couple rounds with your friends. Or–perhaps, alone at home. The options you have for celebrating Valentine’s Day are plentiful, and, should you opt to imbibe, the selection of drinks is far broader than the common choices from which most people select. Here are three classic short drink options for the cocktail aficionado, with names and flavor profiles aptly suited for differing situations and contexts (although you may choose to enjoy them all, regardless of whatever plans for your Valentine’s Day).

The Aviation – it’s the wind beneath your wings

Just getting to know this person? Want to have a few rounds this evening before dinner without feeling remorse? Best to try the Aviation, a light, floral drink with a lot of interesting flavors mingling together.

The history of the Aviation is a long one: originally listed by Hugo Ensslin in this book, Recipes for Mixed Drinks, published 1916, the cocktail called for crème de violette. However, over the years, other ingredients started being used instead, as crème de violette became increasingly difficult to find inside of the USA. Replacements included Parfait d’Amour, Crème Yvette or ultimately blue curacao, used to provide the drink’s characteristic blue hue. For reasons of taste of course, you will likely want to stick with crème de violette, using Parfait d’Amour or Crème Yvette only if you are seeking a cocktail with more citrus or vanilla driven tastes.

The drink is refreshing and light, works well as an aperitif, and also can help to freshen your breath, thanks to the lovely floral scent provided by the violette-based liqueurs. Classically, you would shake the drink (on account of the inclusion of the lemon juice), but if you want to experience the true aromatics in the gin, you can take your time stirring it in order to ensure adequate emulsion and dilution. Note that the precise ratios of this classic recipe are still highly debated, but as we at Styleforum don’t like our cocktails too sweet, we suggest the following:

    • Eight parts dry gin
    • One part maraschino liqueur
    • Two parts lemon juice
  • One part crème de violette

Combine the ingredients in a shaker tin over ice; shake the drink well; serve up in a chilled coupe. Garnish with a Marasca cherry.

The Bijou – or, I couldn’t afford anything from Tiffany and Co.

Just finishing dinner but you need something to relax you further? Or you want to provide a good-looking gem to someone without breaking the bank? Try the Bijou, an herbaceous and heavy cocktail.

Another classic drink, the contemporary Bijou originally appears in Harry Johnson’s Modern Bartender’s Manual (1900). The Bijou, meaning jewel in French, stands strong with a glorious amber hue that entices the imbiber with its smooth mouth feel and attractive appearance. Johnson’s version of the drink is incredibly complex on account of the use of two strong components with plenty of aromatics and layers of flavor (Italian vermouth and green Chartreuse).

The cocktail works better as a digestif, considering the strong body and alcohol content. Historically the drink was made with equal parts, but in the modern day you want to provide a bit less of a kick, so reducing chartreuse and vermouth help to bring the cocktail into the 21st century. Additionally, for this drink, Plymouth gin works wonders, seeing as how both green Chartreuse and Plymouth gin feature coriander, and the creamy body of the Plymouth can extend the already rich mouth feel of Chartreuse and sweet vermouth.

Stirring the cocktail works best, and if your significant other likes strong drinks, this will serve as an excellent nightcap to your most assuredly already enjoyable evening.

    • Three parts Plymouth gin
    • One part Italian (sweet) vermouth
    • One part green Chartreuse
  • 1 dash orange bitters

Combine the ingredients over ice in a mixing glass. Stir the drink to emulsify it well and provide adequate dilution. Strain and serve with a twist of lemon and a Marasca cherry as garnish.

The Widow’s Kisswhen this Holiday just doesn’t suit you

So your evening is spent alone, or you really just want to have a strong drink before bed. The Widow’s Kiss will serve you well.

Likely first published in George Kappeler’s Modern American Drinks (1895), the Widow’s Kiss is a drink that packs a punch on account of the three strong alcoholic components that make up the body of the drink. The drink has seen itself published identically in a few other cocktail guides, including Bill Boothby’s and Harry Craddock’s. As such, despite not being well known, the cocktail serves as a true classic, providing you an interesting drinking experience that is directly a blast from the past.

The Calvados can be replaced with Applejack if Calvados is not available in your area, seeing as how they are similar spirits with similar flavor profiles. Each is a distillate of cider, and both have a wonderful note reminiscent of fall, dead leaves and freshly plucked apples. On the other hand, the Benedictine and the Chartreuse are both historically created by monks, and include numerous herbs and spices that provide strong, memorable flavor profiles that are interesting enough to enjoy neat on their own. Each of these liqueurs have their own notes, but in harmony they begin to exhibit and complement each other, providing a more interesting drinking experience.

The cocktail is incredibly deep and complicated thanks to the herbaceous liqueurs, and the high ABV content of the drink serves well to keep you warm on a chilly night.

    • Two part Calvados (or Applejack)
    • One part yellow Chartreuse
    • One part Benedictine
  • Two dashes Angostura bitters

Pour the ingredients together over cracked cubes of ice in a mixing glass. Stir well, ensuring the drink reaches adequate dilution. Strain, serve up and garnish with a Marasca cherry.

Enjoy your Valentine’s Day, whichever stylish way you imbibe.

e. v. Empey

Here’s What Women Want You to Wear on Valentine’s Day

They say a well-tailored suit is to a woman what lingerie is to men.

I wholeheartedly agree with that, if by “well-tailored suit” we mean a lightweight, effortless, Neapolitan-style suit in an interesting color combination.

Perhaps it’s the Italian blood pumping in my veins, but I love a man that is confident enough to pull off a spezzato and walk into a room and throw his cashmere coat on top of something, suede loafers softly tapping on the ground (I’m still not over the crush on my ex-Latin professor. Don’t judge me).

However, a suit is not the only garment that can cause hormonal upheaval in women. Here’s a shortlist of my favorite menswear items:

  • A Turtleneck
    I believe that there is a science behind my love for turtlenecks. The fact that they protect one of the most delicate parts of the human body triggers in me the idea that the man wearing it is sensible and vulnerable – my favorite type of people. The fabric rolls gently on that spot between the jawline and the ear that is made to whisper secrets and give furtive, breathless kisses. Plus, the Italian word for “turtleneck” is dolcevita. Need I say more?


  • A Black Leather Jacket
    I like a man wearing a black motorcycle leather jacket for the exact opposite reason I like a man wearing a roll-neck sweater. It screams confidence, and it gives off an attitude women cannot resist. We all pretend not to be submitted to the charm of an asshole, but the reality is that, while in our minds we swear we would never fall for someone like this (“Who, him? That pretentious, self-centered, reckless egomaniac?”) he is already smoking his #cigaftersex.


  • Imperfection
    I know I’m walking on eggshells here, but I’d like to stress the point that perfection is not sexy, and neither is an obsession with clothes and how they fit. Please understand that no woman will ever be up at night thinking “Sacrè Bleu! That half-break on his suit pants was so neat!” or “Hell, that blazer had no pulling whatsoever,” nor will any woman ever cradle the fantasy of involving your tailor in a hot ménage à trois. If you really want your suit to look sexy, throw it against a wall right after buying it, and don’t show up without a glass of whiskey in one hand and a cubano in the other. Ties are hot only when they’re loosened up and don’t squeeze your neck to the point your eyes look like they’re about to pop out any minute, but just FYI, when it comes to going at it, they’re the male equivalent of a bra: we never know where to start taking off the damn thing.



Date Night Outfit Inspiration from SF Members

There are many ways to approach dressing for a date, whether or not it falls on Valentine’s Day. Most of them boil down to your company and your destination. Going ice skating (which we don’t recommend, at least for first-timers – a broken wrist or fractured coccyx is hardly romantic) necessitates a different wardrobe than hot air ballooning, which necessitates a different wardrobe than a nice dinner. With that in mind, let’s take a look at some outfits submitted by Styleforum members that are the perfect date night outfit inspiration.

1. If you’re going tailored, nail it.

An outfit based around a poorly-fitting sport coat is worse than a great casual outfit, so if you’re trying to impress your date, don’t half-ass it. And unless you’re actually having a black tie dinner, avoid severe outfits – no black suits, please. A luminous blue or a pleasing grey is a fine choice, as are any number of odd jacket and trouser combinations. Here are some great examples to get your creative juices flowing.

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2. A Leather Jacket is Always Good

If you’re spending your time outdoors (or in) and the weather is nice enough, a leather jacket is a great option. You can wear a classic double-rider or moto with jeans, or with a shirt and trousers; and other, more experimental options may be a great way to work something new into your wardrobe. Besides, just about every guy looks good in a black leather jacket, and it’s one of those garments that just screams “touch me.”

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3. Go Casual

You don’t have to wear a suit (or a leather jacket) to look great. If you want to draw the eye, try a beautiful color instead of your standard black or grey, or aim for great texture. Again, try to let your personal style show through. You want to come off as you, not a giant reptile wearing the skin of a human. And as always, you want to be comfortable – so comfortable, both mentally and physically, that you’re focusing on having a good time with your date and not fidgeting with your clothing.

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5 Valentine’s Date Style Mistakes to Avoid

Whether or not you go all-out on Valentine’s Day or treat it much the same as any other, there’s a good chance that, even subconsciously, you’ll want to impress that special someone. It doesn’t matter if you’re headed out on a first date or celebrating a multi-year anniversary – these Valentine’s Date style mistakes should be avoided at all cost!

1. Don’t Wear Way Too Much Cologne

If you’re fancying yourself up for a special date, you might be tempted to spritz on a little bit extra in order to crank up the sex appeal. The thing is, you don’t need to be broadcasting your scent to the world at large (you probably shouldn’t be doing this anyway). Save your favorite fragrance for the person who matters, and avoid being “that guy” at the restaurant.

Your usual application can be altered or supplemented with some clever placement, though. Instead of sticking to just the wrists or behind the ears, add a dab at the hollow of your throat or base of your sternum. Your body heat will make it project just fine, while keeping the scent intimate so that your partner is the one who benefits – especially if they find the opportunity to lean in close.

If you’d like some suggestions on the perfect Valentine’s Day fragrance – either for yourself or to give as a gift – check out our Fragrance Thread.

2. Don’t Wear the Same Thing You Wear Everyday

Your date’s not going to be impressed if you show up wearing the same pair of distressed jeans you’ve worn every other time you’ve seen them. Headed out to dinner? Maybe try a new tie you haven’t worn before, or a slimming black turtleneck worn under a jacket. If you’re headed out for a fancy evening, maybe use it as an excuse to bust out the peak lapels and grenadine tie. Or, take a play from resident black-tie aficionado @Andy57 and wear a dinner jacket out to dinner. Changing things up – even if it’s just wearing black denim instead of your usual blue – will turn your date’s eye and let them know that you’ve made an effort.

Looking for outfit inspiration? Try one of our three fantastic What Are You Wearing threads:

3. Don’t Shower Ten Minutes Before Your Date

Being clean is great – really. Whatever you’re doing, no one wants their date to show up to smelling like day-old sweat, covered in filth from the road. But make sure you give yourself time to scrub and dry before you head out for the evening. Rushing at the last minute to clean yourself, pick an outfit, and get to wherever you’re going on time is a great way to show up a sweaty, sticky mess.

Give your hair time to dry so that you can style it – heck, maybe even blow dry it. Showing up with a wet mop on your head doesn’t tend to impress. If you’re shaving, give your face some time to calm down with a soothing cream or aftershave balm. And don’t forget the deodorant! Stress can be stinky, and that’s not what we’re after here.

4. Don’t Go Too Far Out of Your Comfort Zone

If you’re a Styleforum reader, chances are you’re on your way to being pretty well-versed in a number of different styles. Plenty of us are inclined to experiment with new or interesting garments, whether you’re a fan of tailored clothing or of streetwear. That said, part of feeling great on a date night – whether it’s first date or five hundredth – is feeling good in what you’re wearing.  You’ll be more comfortable, more confident, and more focused on having a good time – rather than fidgeting in something you’re not 100% certain of. So, when you’re picking out your Valentine’s Day date outfit, understand that it’s maybe not the time to experiment with something you’re not sure you’ll love.

If it makes you feel like fidgeting, if it makes you feel like you’ve got to suck in all night, if it makes you feel like someone who isn’t you – take a step back and pick a different outfit. After all, there’s nothing more unpleasant than feeling uncomfortable in your own skin – and your date will pick up on it too.

Note: that includes the wearing of brand-new shoes. If you’re focused on how much your feet hurt, and how many blisters you’ll have the next day, you’re not going be focusing on having a great time. What if you end up dancing?

5. Don’t Neglect the Details

Again, this is an opportunity to show your date that you take them and their company seriously, so here are some last-minute tips that go beyond just picking an outfit:

  • Don’t tie your tie like a slob – make a perfect dimple.
  • Don’t (EVER) match your tie and pocket square.
  • Do Brush your teeth.
  • Do trim your nose and ear hair.
  • Do take a minute to shine your shoes.
  • Don’t neglect your table manners.
  • Do give some consideration to your undergarments, if that’s the direction your day might take. Give the Bart Simpson boxer shorts a rest.

If you avoid these Valentine’s Date style mistakes – and they’re easy to avoid, so you have no excuse – you’ll be on your way to enjoying this most Hallmark of Holidays.