Valentine's Day Outfits For All Phases Of Your Love Life

February—the month couples around the Bay Area get elated for. Chocolates, champagne, and a reason to get dressed up. It’s the month to show your love that you are ultimately are the right choice. Same can be said for first dates, friends, and even S.A.D (Singles Awareness Day).

The Valentine’s Day outfit is a direct reflection of how you want your date to perceive you. The color-ways, the fabric, the accessories, the way items fall on you—for better or for worse, it’s the first and last impression you make. With every outfit, it’s a staple in your timeline that makes you remember where you were, and how the date came to be. The bomber that you got avocado toast in, the dress that you accidentally said “I love you” in—the outfit you created timestamps these particular moments. When SFGoodwill and Bob Cut came together to curate outfits for every phase of your love life during this romantic filled month, we hit the ground running.

In a city where luxury retail tempts your wallet—finding a complete outfit for under $50 (which is all of these outfits below) is exactly what every San Franciscan wants ultimately. And your contributions to thrifting don’t go unnoticed—SFGoodwill provides second chances and training for local people in need. Store revenue funds job training programs for local people facing barriers to employment. An organization that puts people and planet at the heart of their mission.

These outfits we designed and constructed alongside Goodwill of San Francisco, San Mateo and Marin Counties, these pieces were found at the Goodwill stores on Clement, Fillmore and Haight! These outfits represent a variety of comfort, price, and style aspects that can be inter-swapped between each other. How magical is that? Which one is your favorite? Let’s discuss.

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The First Date

A sense of the jitters, you want to flex comfortability and stylish undertones. Luckily for you, you chose a casual meeting spot like Boba Guys on Divisadero St. An outfit that’s easy to sit in, a denim jacket that keeps you warm (just in case of SF’s micro climates), and easy to walk-in—just in case if the date goes from one hour to eight hours. We also recommend a clutch or some sort of bag that can keep you belonging all in one place but still have an essence looking together. The goal here is comfort because it already takes a lot of nerve and confidence to meet someone you inherently don’t know. // Bird dress; Maeve, denim jacket; Old Navy, shoes; Cole Hann. Shop the look here.

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The Anniversary Date

You’re the wow in their life—let’s be real, you’re clearly a stunner. So why not dress like one? This is where the heels can be thrown into this outfit’s chemistry. Creating a longer silhouette against the flowiness of a pleated skirt engages your dominance in the room. And we didn’t forget about the comfort factor, this Marc Jacobs sweater is the balance between practicality and style. So whether you have reservations are Che Fico or a chicken sandwich date at Mini Bar—your outfit is interchangeable. // Metallic sweater; Marc by Marc Jacobs, Skirt; unknown brand, shoes; Nine West. Shop the look here.

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The Friend Date

For those who identify heavily with “S.A.D” (Single Awareness Day)—a day to go out with your best gal pals is seriously needed. Whether you’re hitting up the farmers market to then devour brunch—being in an outfit that allows you freedom is a blessing in disguise. Giving yourself pops of color to remind the fact that today is indeed beautiful and that self-love is in the air. Wear the pieces you don’t get flaunt on the daily basis—it’s the perfect time to give this outfit some fresh air. // Blouse; Equipment, denim; Bullhead Denim Co., shoes; EG Shoes. Shop the look here.

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The Heartbreaker Date

Maybe Valentine’s Day isn’t all the ooey-gooey romance you need—this date may just be needed to break things off in a civil and adult manner. But a heartbreaker type outfit should ensue when you clearly need to look like you mean business. There around about 1 Million fish in the sea and for you, you’re still fishing. In an outfit where you’re breaking it off. Keep a casualness that helps lend itself to highlighting pieces from you look, i.e these skin colored leggings falling into a pair of heels. // Sweater; Brandy Melville, shorts; Zara, jacket; Jackson, shoes; Sole Society. Shop the look here.

// You can source your outfits this holiday season at the Goodwills of San Francisco, San Mateo and Marin Counties. We constructed our outfits at Goodwill Haight and Goodwill Fillmore (1700 Haight St, San Francisco & 1669 Fillmore St, San Francisco.) In case you can’t go to the stores physically, you can shop Goodwill here: https://www.ebay.com/str/goodwillsanfrancisco. Photography by Anthony Rogers, styled by Nichole Kreglow, modeled by Alyssa of SCOUT Modeling and Talent.


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