Style

What to wear on Valentine's Day: 9 outfits to suit any date, from dining to hiking

Valentine's Day is almost here and the date plans are made, but what will you wear? Everyone wants to look their best without looking like a walking Sweetheart candy or Hallmark card.

No matter what your date plans, here's how to get into the holiday spirit without looking silly.

New couple or a first date

What's the secret to a perfect first-date look? Make sure you feel comfortable and confident.

Samantha Okazaki / TODAY
The key to a great first-date look? Feel comfortable and confident.

On Zach:

Go for a bold pattern! Like this leaf-covered shirt from American Eagle. A young, fun trend to try is the “invisible tie;" get it by buttoning the entire shirt up to the top. Pair it with corduroy skinny jeans — a big comeback fabric in menswear. Top with a cozy, shawl-collar sweater and she won’t be able to resist a hug goodbye.

American Eagle shirt, $40, ae.com; Bonobos corduroy pants, (on sale) $48, bonobos.com; Bonobos shawl collar cardigan, (on sale) $98, bonobos.com

On Melanie:

Target recently partnered with style site Who What Wear to offer a monthly collection of affordable options all under $50.(Amazing, right?!) We love how this striped off-the-shoulder dress works at any age and it’s a great way to show some subtle skin. And the adorable belt bag adds a pop of red while allowing you to be hands-free — in case you hold hands, of course.

WhoWhatWear x Target dress striped Bardot dress, $29.99, in Target stores *dress available online Feb. 28; WhoWhatWear x Target belt bag in Valentine, $24.99, in Target stores

  • Slideshow Photos

    Stephania Stanley

    First date makeup guide to try this Valentine's Day

    Makeup artist Lauren Cosenza shares her expertise on nailing the ever-elusive "no makeup" beauty look.

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    Prime your skin

    Start with a nourishing primer for soft, supple skin and to create a smooth canvas for makeup. Apply using your fingers. 

    Photos: Stephania Stanley, Makeup: Lauren Cosenza
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    A touch of glow

    Warm the skin with BB cream bronzer, with emphasis on the cheeks, hairline and jawline.

    Stephania Stanley
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    Get wet

    Go for the wet look on eyes with an eye gloss (we used Rouge Bunny Eye Gloss).

    Stephania Stanley
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    Define

    Subtly define eyes by rimming them with a sexy metallic shadow and then immediately smudging the liner for an effortless, worn-in effect.

    Stephania Stanley
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    Lash it up

    Coat your lashes in a defining and enhancing mascara, like Maybelline Lash Sensational Luscious Mascara.

    Stephania Stanley
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    Leave them shiny

    Cover lips in a sheer lip-enhancing gloss that nearly mimics your natural color. Hint: That's the secret to kissable lips.

    Stephania Stanley
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    Looking fab!

    Stephania Stanley
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    Leave hair loose, natural and soft. That way, it seems innately touchable.

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    Pair with a subtly sexy halter or spaghetti-strap top and some earrings that swish.

    Stephania Stanley
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    Your date doesn't stand a chance.

    Stephania Stanley

Adventurous or active experience

Valentine’s Day is the perfect excuse to share a memorable experience together. Mix it up by going hiking, ice skating or rock climbing. Luckily, the athleisure look is still in style, with plenty of cool options to choose from. The key is to layer so that you can go inside and out comfortably.

Samantha Okazaki / TODAY
Sporty and fun never goes out of style.

On Jerry:

By now you’ve seen men’s joggers a thousand times, but khaki is the latest iteration and classier than the original. This universal fabric keeps the outfit from looking sloppy — or like you're wearing sweatpants.

American Eagle joggers, $50, ae.com; Old Navy quilted chambray shirt jacket, $60, oldnavy.com; Old Navy henley shirt, $10, oldnavy.com; Knockaround sunglasses, $10, knockaround.com

On Gabby:

This outfit is cute enough to take you from a walk in the park straight to brunch without skipping a beat. Don’t be afraid of playful patterns and bright colors — that’s the fun part! (And they will look great in your social posts). Accessories are the name of the game: this fun pom-pom hat paired with reflective sunnies will take your outfit to the next level.

Old Navy leggings, $21, oldnavy.com; Uniqlo ultralight down vest, $38. uniqlo.com; Uniqlo hoodie, $30, uniqlo.com; Neff ‘Lulu’ beanie, $30, amazon.com; Knockaround sunglasses, $10. knockaround.com; Adidas ‘Superstar’ sneakers, $89, finishline.com

  • Slideshow Photos

    Stephania Stanley

    'No makeup' makeup to try this Valentine's Day

    Makeup artist Lauren Cosenza shares her expertise on nailing the ever-elusive "no makeup" beauty look.

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    Start simple

    Apply a sheer layer of MAC Face + Body Foundation, or any other non-heavy, non-cakey formula.

    Photo: Stephania Stanley, Makeup: Lauren Cosenza
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    Layer lightly

    Pro tip: Emulsify (in other words, diffuse) the product using your fingertips and press it in with the brush for a second-skin finish.

    Stephania Stanley
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    Fill in brows

    Anchor the face by filling in brows with a brow gel. We used Ecobrow.

    Stephania Stanley
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    Dust a bit of shadow

    Sweep on a wash of natural, soft brown shadow over eyelids. 

    Stephania Stanley
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    Love your lashes

    Gently define lashes with a round wand (to ensure you reach every lash).

    Stephania Stanley
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    Nothing but nude

    Paint lips with a light pink or nearly nude color. We tried NYX Matte Lipstick in Nude.

    Stephania Stanley
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    Look at you, natural beauty!

    Stephania Stanley
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    Who's ready for a weekend upstate or a hike?

    Stephania Stanely
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    This may just be your new everyday look.

    Stephania Stanley

Classic dinner date

Take a cue from your dinner date by wearing well-fitting classics … and bump it up a notch with cute accessories!

Samantha Okazaki / TODAY
This adorable couple is celebrating their 23rd wedding anniversary!

On Frank:

The window pane print is a hot trend right now for men of all ages. The pattern is subtle compared to a traditional plaid or tartan, while still feeling dressier than your everyday flannel. And for a touch of Valentine's Day fun, pair with these adorable heart socks.

Old Navy shirt, $35, oldnavy.com; Old Navy straight fit jeans, $35, oldnavy.com; Old Navy heart socks, $4, oldnavy.com

On Debbie:

These vegan leather moto pants from Melissa McCarthy’s new fashion line are especially cool in this deep plum color. See, there’s no need to stick to all black to rock a flattering look! And this embellished-shouldered top will frame your face beautifully. Candlelight at the dinner table will reflect off the gems and literally make you shine!

Melissa McCarthy moto skinny pants, $98, melissamccarthy.com; Melissa McCarthy embellished sweater, $118, melissamccarthy.com

  • Slideshow Photos

    Stephania Stanley

    Valentine's Day ideas: Step-by-step makeup for a classic dinner out

    Makeup artist Lauren Cosenza breaks down the classic smokey-eye-and-red-lip combo into six easy steps. Perfect for your V-Day date!

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    Prep with primer

    Prep eyes with Mehron Primed eyeshadow primer to keep eye makeup locked in place for hours. 

    Photos: Stephania Stanley, Makeup: Lauren Cosenza
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    Create a smokey base

    Use Maybelline Color Tattoo Sticks in Creamy Chocolate and Bronze Truffle as the cream base color for your smokey eye.

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    Finish with cream shadow

    Top the cream base color with MAC Bronze (powder) eyeshadow for added intensity.

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    Highlight

    Highlight the inner corner of the eye with Maybelline Color Tattoo Stick in Bone Beige.

     

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    Line eyes and apply mascara

    Apply NYX Jet Black Eyeliner to the waterline and tear line – followed by several coats of mascara.

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    Complete your look with a pop of red lipstick

    Balance the dramatic eyes with Dermalect 4-in-1 Smooth Lip Solution in Obsessive, a spicy red.

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    And there you have it!

  • Valentine's Day ideas: Step-by-step makeup for a classic dinner out

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    Enjoy your date!

    Pair with your favorite LBD and leave your hair long and shiny to finalize your look.

Girls' night out

Valentine’s Day isn't just for your sweetheart: It can be a great reason to spend time and celebrate with anyone you love! A great night out with your gal pals can be just what the doctor ordered. Go for a fun, fashion-forward look — and don’t forget your dancing shoes!

Samantha Okazaki / TODAY
These girls are ready for a night out on the town.

On Vidya (far left):

Red doesn’t have to feel so obvious on Valentine’s Day, especially when it’s this fiery color that the company describes as “Sriracha.” Cutouts will be a huge trend this spring and are much easier to pull off than they seem. Remember: Your waist is the smallest part of your body, so go ahead and show it off!

BB Dakota ‘Keegan’ jumpsuit, $98, articleand.com; Baublebar ‘Rhiannon’ earring crawler set, $36. baublebar.com; Aldo ‘Tiege’ pumps, $43, aldoshoes.com

On Brooke (center):

If you can’t let your inner rock star shine while out with your girlfriends, then when can you? This outfit is begging for a night out on the town and mixes two major trends of the moment: fringe and minimalist camisoles. We love how this kimono from BB Dakota — which will hide all of your sins — has a subtle floral print that keeps it feminine without feeling too over-the-top girly.

Jack by BB Dakota ‘Rosalynn’ kimono, $75, shopbop.com; Old Navy mid-rise rockstar jeans, $32. oldnavy.com; Baublebar ‘Excelsior’ collar, $38, baublebar.com; Wilfred ‘Boscono’ camisole, $55. aritzia.com

On Morgan (right):

Pretty and feminine doesn’t have to feel dated. This flattering wrap dress with butterfly sleeves is sweet enough to look appropriate, yet sexy enough to hug all the right places. Styled differently, you could even wear this to work!

Topshop wrap dress, $80, topshop.com; Old Navy faux suede bag, $17, oldnavy.com

  • Slideshow Photos

    Stephania Stanley

    Valentine's Day ideas: Girls' night out makeup look

    Makeup artist Lauren Cosenza breaks down the ultimate girls' night out beauty look. Try it out this Valentine's, I mean, Galentine's Day.

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    Get glowing

    Add some warmth to your face with MAC Give Me Sun Mineralize Skinfinish Bronzer.

    Photo: Stephania Stanley, Makeup: Lauren Cosenza
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    Add some sparkle

    Dust a sooty, sparkly metallic shade (we used Laura Mercier Black Karat eye shadow) over lids and under lower lashes.

    Stephania Stanley
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    A touch of gold

    Pat a bit of gold shadow (Mehron Metallic Powder in Gold) only in the center of the lids.

    Stephania Stanley
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    Line it up

    Line eyes in a dark brown pencil (like NYX Brown Perfection eye pencil).

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    Make it spicy

    Pop your lips with a punchy, playful orange-red like Rimmel Call Me Crazy lipstick.

    Stephania Stanley
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    Looking sultry!

    Stephania Stanley
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    Accessorize it!

    Pair your playful makeup with a cute braid and some fun earrings. A sparkly shirt never hurt, either.

    Stephania Stanley
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    Ready to paint the town red!

    Stephania Stanley
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    And hit up the dance floor, of course.

    Stephania Stanley
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