6 Valentine’s Outings & How To Style Them

6 Valentine’s Outings & How To Style Them

Oh dear - another Valentine's Day article. Hear me out, if you're barely holding it together and symbolically burning tacky Hallmark cards just to feel something, this isn't just another "how to dress for the love of your life" editorial piece. You can still knock them dead regardless of which 'first date' you're going on.

Oh dear - another Valentine's Day article. Hear me out, if you're barely holding it together and symbolically burning tacky Hallmark cards just to feel something, this isn't just another "how to dress for the love of your life" editorial piece. You can still knock them dead regardless if you have a classic awkward dinner res with that guy on Hinge you've been talking to for half the pandemic, or an inaugural Zoom date with your one-that-got-away crush from high school. You can still dress the part if plans include group dates with besties or hosting a casual wine night with sisters-in-single-solidarity.

Whatever you're doing this year, this is your essential style inspiration to slay this international day of romance:

1. Girl's Date Night

Pictured (something similar): Mini Lady Dior Bag, DiorH&M (something similar) Dress Pants, Ralph Lauren (something similar) Wool Crepe Blazer, Stuart Weitzman, Nudistsong Heels

In the words of Leslie Knope on Gal-entine's Day, “You shut your mouth, you have all the strengths.” If February 14th is just another day or god help us, a cursed one filled with traumatic flash backs, plan a first of many 'girl's night'! The key on girl's night is to look sexy as all hell for no one but yourself. If you're in need of a serious confidence boost - roll up to the first recurring dinner (or brunch) date in a matching trouser-blazer set with a sparkling bralette underneath. It's daring, beautiful, confident - just like you. 


2. Business-Romantic

Is business romantic a thing? Anyway, whether you love or hate Valentine's Day, that shouldn't dictate who gets to rock the boldest color known to us. The classic red lip? Yes. How about a matching pant suit? Even better. If you're going out for the first time this winter (no judgment, because, same) style it like the inspiration for Girl's Night. If you're heading to a late meeting or going out with work friends, throw a high-collared shirt underneath for a more professional fit. 


Pictured: Zara (something similar) Blazer, Dior, 30 Montaigne Bag, Everlane, The Pima Micro-Rib Turtleneck

If you still want to dress this look up a bit, focus on decking out your ears and wrists. Ear parties are perfect ways to not only elevate any look but make even the most basic outfits pop - perfect for a night out when you just want to throw together an outfit quickly.  

3. Brunch-love

You didn't think I'd leave out brunch-style, did you? My suggestion is if you have never done so before, take yourself out on a brunch date. You deserve it and you don't need anyone on your arm in order to drink champagne at 10:00 AM with a side of one-of-everything.

The reason I'm so hyped up on brunch this year is because people are finally accepting that casual brunch is a thing! In downtown Toronto and probably every other city on earth, women are showing up to Sunday brunch in cocktail dresses and heels. All the power to you if your ankles can handle Jimmy Choo's before noon, but in the spirit of the lingering working-from-home vibes, style your hash browns with ath-leisure. That's right, no need to change out of your sweatpants, ladies. 

Image: Glamour
A shin-length teddy, a half-moon bag, and the Winter 2022 trending Moon Boots; a brunch buffet has never seemed more possible. I had to go with the cherry color example to be on theme, of course! If you're wearing ath-leisure out, dress up your outfit with a trench coat or teddy, a hat and bag, and a layered look over-top of those leggings. If you're in a hoodie or crewneck - focus on elevating the look with accessories like sunglasses and earrings


4. Night In/Night Out

Say you have a date with that cheeky merlot on your counter and watching Notting Hill for the thirtieth time, and you get the Bat signal from one of your friends: come out. No need to panic. What you need is an action plan. If you're already in you silk pajama set - why bother changing? It's time to accessorize. Add strappy heels, layered chunky jewelry, and a clutch or bag that matches your 'sleepwear' suit. Because sleepwear is also street-wear if you style it correctly. Plus, sillk will always look sleek. 

Pictured: Zino Official, Eda Shirt in Silk, Bulgari, Crossbody bag, Stuart Weitzman, Nudistsong Heels

5. Actual Date

If you find yourself asked on a legitimate first date this year - take it as an opportunity to go full throttle in the style department. I'm talking hair, makeup, dress, heels, and accessories. Seriously, when is the last time you put thought into your ear party? Use this as an excuse to try new things like huggies, threaders, pearls, and chains to layer your necklaces and bracelets and dress your ears to impress. 

Pictured: Verie, Diamond Cuff with Chain 

If you're not in a climate which allows comfort when wearing a slip dress and open-toed heels, or you're having a casual drink with a soon-to-be non-casual, look dashing by candelight in a brownstone-inspired casual outift (pictured below).

Pictured: Veronica Beard, Oria Glen Plaid Dickey Jacket

Put the outfit together with a sheer white-buttoned blouse and a tweed or plaid jacket over-top. You can either match the jacket with trousers or if you're in a warmer climate, high-waisted pleated shorts and heels. Complete the look with stacked bracelets or a dainty chain necklace overtop of your buttoned-up blouse collar. 

Pictured: Fendi Beige Short (something similar) Revolve, Lilly High Waist Short, Malone Souliers, Alessandra 70MM heel

6. Red-Themed Party

Are you so deprived of social interaction that your friend group will use literally any 'holiday' to host a themed event? If so, you're in need of color-coordinated outfits that fit the day. Valentine's Day is all pinks, reds, and whites; but try patterns this year. This is an easy way to stand out in a sea of heart-colored lovers with red skirts and pink tops.

Pictured: Stuart Weitzman (something similar) Stuart 100 Stretch Bootie

If you just can't bring yourself to wear the bold shades, use small statement pieces of red and pink and lean into colors that will make them stand out - like a white dress with your favorite red lip (ours right now is Chanel's Rouge Allure Shade 99 because it's super bright and bold) or a black dress with a pink bag. 

Pictured: Leia Heart Necklace & Arya Choker

For a really chic and subtle fit, try a red tartan or plaid skirt (trending this season) with bold accessories against a white background like what Valeria's wearing below. A white shirt allows those chunky gold chains, black boots and most importantly the red skirt truly pop. All you need is a brick backdrop and you've engineered your own V-Day photo campaign. 

Pictured: Verie, Drew Sunglasses in Black, Plaid Skirt (thrifted!), The Frankie Shop, Eve Padded Muscle Shirt, Martha Calvo, Initial Lariat necklace

If you're really into the color of the season - matching your boots or heels to your outfit for a fully blushing red look will fit the bill. Same colors in accessories might be a bit much when you're working with bold colors like deep reds - so pair this look with a more subtle black, white, or beige bag. 

Pictured: Fendi (something similar) Peekaboo Isseu Small bag


Read Next: 8 Hacks To Instantly Look More Attractive

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