Valentine’s Day Style for Your Big Date Night (or Day)!

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date night looks

Valentine’s Day is coming in a few weeks! That means it’s time to spend some special time with our loved ones. Whether you have a fancy night out planned or a casual family game night at home, these V-Day outfit ideas have you covered. All items shopped for on, because we all like shopping in our pajamas! 


Date 1: Dinner & Dancing

The traditional date night includes a fancy dinner and a show or dancing! This Astr the Label midi dress ($53.40, reg. $89) is the perfect balance between sexy and classy. Bonus: it comes in ten colors! For the classic Valentine’s vibe, go for the rust color pictured here. Elevate the traditional neutral heel with a fun texture, as in these metallic Sam Edelman ankle strap sandals ($120). Throw your essentials in a glittery clutch like this Leather Pouch Wallet from Madewell ($29.50). It doubles as an inner pouch for your bigger bags during the week.

Date 2: Casual Dinner & Movie

My favorite kind of date is the one where I can have margaritas and queso for dinner then get absorbed in an entertaining movie while holding my hubbies hand. This kind of date calls for the perfect pair of skinny jeans (with just enough stretch!), like these Good American High Waist Ankle Skinny Jeans ($159). Add a neutral top like this side tie blouse from Topshop ($55), and a statement jacket like this 1901 pink and gray plaid blazer ($139). Add a little sexiness by cuffing your jeans and wearing these trend right Steve Madden sock booties ($99.95). These pieces can all be repurposed for other types of outfits, which make them great investments.


Date 3: The Day Date

My favorite day dates are wine tasting and (obviously) shopping. A champagne lunch needs to be thrown in somewhere in there. For the day date, you want to look daytime appropriate but still sexy and chic. This Boden Juliet Jersey Midi dress ($150) fits the bill! The bright colors and chevron stripes are flattering and the jersey material is flowy and fun to wear. Try pairing a jersey dress with a knit moto jacket like this Liverpool Stretch Cotton Moto Jacket ($98). A minimalist mule like this Cole Haan Piper Mule in misty rose leather ($100) fits the cheerful vibe and will be easy to walk in for a stress-free day date. 

Top it all off with a pair of glossy acrylic hoops like these Kennedy Hoop Earrings from Cult Gaia in Carnation ($88).



Date 4: The Outdoor Date

This date involves some exercise. Maybe it’s a hike on the Land’s End Trail or a bike ride in Golden Gate Park, followed by a picnic with your family. You can still plan a super cute outfit for this kind of date. Start with the classic Three Stripe Adidas leggings with a fun pop of pink ($60). Add a top that will make you feel good from the inside out, like this one from Spiritual Gangster ($48), and top with an ALO Foxy Faux Fur Jacket ($188) that will keep you cozy in the fog while looking stylish. Invest in some new kicks that will go with all your workout outfits, like these light bone color Nike Cortez sneakers ($90).


No matter what you decide to wear, enjoy your kid-free time together. Cheers to style!

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Laura is the founder of Merry Styling, a mom of two, and a former teacher who lives in San Francisco. She grew up in Columbus, Ohio and relished the changing of seasons because it meant revamping her wardrobe! After completing graduate school at The Ohio State University, Laura relocated to San Francisco, where she taught elementary school for nine years before having her two children Noelle (6) and Lucas (2). When her youngest was six months old, Laura started working as a stylist with jewelry and accessories company Stella and Dot. Since then, she has earned a Fashion Merchandising degree from the Fashion Institute of Design and Merchandising, styled with nonprofit Dress for Success, and done various merchandising projects for different retail organizations. Laura knows that style is more than clothing and accessories. She has found it to be an amazing confidence booster. Finding the perfect outfit on a bad day can turn it into a great one. She is especially passionate about working with moms Laura started Merry Styling because she wants to help other moms and anyone else who feels "left behind by fashion" to feel confident, empowered, and beautiful through personal styling, closet detox, and personal shopping sessions. Follow her at @merrystylingsf on Facebook, @merrystyling on Instagram and check out for more!


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