WHAT TO WEAR: Valentine’s Day Date Outfits

By Madison Gillespie


Valentine's Day Date Ideas - Try New Restaurants


Tonight’s the night.  Tonight’s the night of blurred candlelight and fluttering hearts, of love both new and old.  It’s Valentine’s Day, but this romantic holiday is no simple affair.  Many who celebrate this holiday are fueled by expectation, determined to have nothing short of a perfect evening.  One of the biggest challenges in preparing for Valentine’s Day is choosing the right outfit, an ensemble to take your date’s breath away.  Finding the winning look is complicated by the type of date you will be going on.  A candlelit dinner in an upscale restaurant requires different clothes than a date to the movies, but with a little guidance, you will be able to dress for anything.  Here are some sample outfit ideas for a variety of potential Valentine’s Day dates.


Date #1: Ice Skating

Ice Skating

With winter’s tingly chill in the air comes a plethora of seasonal dates, one of the most popular being ice skating.  Whether you can glide effortlessly across the ice or can’t go a few steps without stumbling, ice skating is the perfect activity to incorporate into your Valentine’s Day festivities.  It is a fun and active way to spend the evening, and you and your date can catch each other if you fall.  Here are some tips for a cute and practical outfit so you can take on the ice like a pro.

  • Since you will be outdoors, staying warm will be your first objective.  At the same time though, you don’t want your ability to skate to be hindered by a heavy winter coat.  Layering a quilted down vest over a tight-fitting sweater will give you the same level of warmth, but with increased mobility.
  • Fleece-lined leggings add extra warmth to the ensemble, and their stretchy material will allow you to skate with ease.
  • Instead of focusing heavily on jewelry, adorn your look with adorable wintry accessories like a pom pom knit hat, detachable gloves/mittens (to better hold your date’s hand with!) and fuzzy boot cuffs.
  • Make sure to wear a crossbody purse that will remain securely on your body as you skate.


Date #2: Dinner and a Movie

Dinner & A Movie

Dinner for two plus the latest box office hit is a staple date any time of year, but especially on Valentine’s Day. Exchanging smiles and laughs beneath the mood lighting of the restaurant and snuggling close in the theater is a guaranteed way to generate sparks. Here’s how to come up with an outfit that will make this classic date into a night to remember.

  • Button-up skirts are an extremely trendy item this season and would make an excellent addition to your look.  They come in multiple varieties; you could choose one with more fit or flare to better suit your style.
  • Tucking a slightly oversized turtleneck into the skirt will create a charming, endearing feeling (and give you some extra warmth as you are wearing a skirt).
  • You can add extra charm by curling your hair.  There’s nothing quite as adorable as some bouncy, doll-like ringlets!
  • Pairing tights with heeled booties will give more of a presence to your ensemble.
  • Wearing a long necklace with your sweater will add length to the outfit and draw more attention to your look as a whole.
  • Make sure to bring a large purse to help smuggle in food – Valentine’s Day is already expensive enough!
  • A long woolen pea coat will make a good blanket for your tight-covered legs in the theater.


Date #3: Formal Dinner

Formal Dinner

This is by far one of the most popular Valentine’s Day dates.  A meal from an expensive restaurant is bound to make your evening even more romantic and special.  However, the luxurious setting puts extra pressure on some when selecting an outfit.  There’s no need to be nervous, though.  Use the following suggestions as your guide, and you will be beautifully suited for any five-star establishment.

  • A fancy restaurant certainly calls for a wow moment.  However, that does not mean you should dress outrageously; overdressing in this instance will achieve the opposite effect.  Instead, be simple and tasteful. Let the little details speak for themselves.
  • Try a spin on the little black dress.  Choosing something tight in the waist with flare in the hips will give you a classically beautiful look.
  • When selecting accessories, try out nude or blush tones that will blend effortlessly into the ensemble.
  • Wearing a cape increases your elegance and will be easier to remove than a coat.
  • Pair your neutral accessories with a bold red lip.


Date #4: Movie Night at Home

Movie Night:Netflix

Staying in on Valentine’s Day means quality cuddle time with your significant other and a plethora of romantic movies at your disposal- a sweet and cozy way to spend the evening.  Here’s some advice on how to dress to maximize your Netflix-fest.

  • The goal here is to be cute and comfortable at the same time so that you can snuggle up with your date; if you try to make your outfit too fancy, it will be difficult to really get comfortable.
  • Wearing an oversized knit cardigan is the perfect way to stay warm and cozy.  Pairing it with a chiffon tank will add some elegance to your look.
  • Fuzzy socks will keep your feet nice and warm, not to mention they are super cute!
  • Keep jewelry to a minimum as it could scratch you or your date, or snag on something as you cuddle.


Date #5: The First Date

First Date.png

Some lucky individuals will be spending Valentine’s Day on their very first dates- a thrilling time in the world of young love, but not so much when planning an outfit.  Because it is the first date many become nervous, especially when they don’t know the other person very well.  The best thing to do is to choose a look that can be applied to any type of date.  That way, you can focus your attention not on your clothes, but on the person you’re about to spend the evening with.

  • A loose sweater with a chiffon/lace hem is an adorable and on-trend item to wear.
  • Layer a plaid blanket scarf over your sweater to add some more warmth and charm.
  • Tight black leggings will balance out these looser items.
  • Keep your accessories cute and simple; rose gold is a recommended color as you search.
  • Take a large bag to ensure that you will have anything you may possibly need for this date.
  • An olive green jacket/coat is a classic and appealing outerwear choice.
  • An additional tip for hair and makeup: since you may not necessarily know your date very well, keep your makeup beautifully simpleCascading curls and a soft red lip are all you need.



*Image Sources:

Cover image taken from https://cbssacramento.files.wordpress.com/2014/01/112.jpg

All other images created with Polyvore by Madison Gillespie

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