5 V-Day Gifts that Your Preppy Significant Other Would Hate

5 V-Day Gifts that Your Preppy Significant Other Would Hate
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Sad Preppy Couple

Judging by Google trends, we spend a LOT of time pondering the perfect Valentine's Day gift. To be fair, it's a tall order. We're supposed to distill a person't entire personality into a single romantic object or act, even if we've known that person for just a short time. Rather than rehash this immensely stressful process, we're taking another tact. You're preppy. Odds are, your significant other shares the same taste. Accordingly, we can make a few deductions about him or her.

So rather than guide you to the perfect preppy gift, we're going to give you some advice that's even more valuable. Here are the top five gifts to avoid at absolutely all costs if you want to keep your preppy significant other. Also, these things are real.

5. Socks for Boat Shoes

Socks and Boat Shoes

What You Think You're Telling Him: "OHMYGOSH! I can't believe we've been together for two whole months! Your formal feels like it was just yesterday! I know you love your Sperrys, but I got you some socks because they're the only shoes you wear, and I don't want you to be cold this Winter, and your feet smell terrible. Love you!"

What's Actually Happening: When it comes to the preppy fashion faux pas, it's hard to find one more egregious than the sport sock/boat shoe combo. Part of the allure of the inimitable boat shoe is that one may wear it in any weather, temperature, or locale, and one need not bother with socks.

Indeed, the sockless ankle is as much a signaling device for status as your grandmother's heirloom pearls. That unavoidable Sperry musk is a badge of pride.

If you suggest to your beau that he cover his preppy toes when he dons his favorite pair of A/Os, you not only run the risk of insulting him, but you also reveal your own fashionable ignorance. For shame! Take the safe road and suggest a nice flip flop instead.


4. A Gift Card for Exercise Classes

V-Day Dos and Donts

What You Think You're Telling Her: "Hey babe, I know you love to work out and keep your body tight and stuff, so I got you some exercise classes so you can hit up pure barre or flywheel or hot yoga or whatever, 'cause I know you love your fro-yo at the d-hall. Text me!"

What's Actually Happening: This should go without saying, but apparently it really needs to be said - don't buy exercise classes for your girlfriend. Just don't do it. Would you buy her a dieting cookbook? Do you think that she likes you for your 45 beer a week physique and former-high-school-athlete-who-just-started-drinking silhouette? You want to stay as far away from this one as you can, chief. Trust us.

3. His & Hers Tribal Tattoos


What You Think You're Doing: "I looove you soooo much, and I'm going to love you forever and ever and ever. We should get matching tattoos so everyone knows we belong together, and I saw Dances with Wolves once, and I thought about going to Burning Man, so I totally think we could pull off the whole "tribal" thing."

What's Actually Happening: Let's revisit what we know about you. (A) You're preppy. (B) You have great taste in websites. While you could probably sneak into just about any country club or deb ball of your choice without raising any eyebrows, you're not going to pass unnoticed in a biker bar or Nickelback concert anytime soon. We recommend you pass on the ink, unless you're willing to cover your back with a full-on Lilly Pulitzer print. Now that's hardcore!

2. A Homemade Needlepoint Boyfriend Belt

Boyfriend Belt

What you Think You're Doing: "I totally love Stephen, and I'm going to give him something special that represents all of the things he loves and all of the things I love about our relationship. I'll make a belt that has his favorite football team and his hometown zip code and an oak tree because he's southern and his fraternity letters because he's a frat lord and..."

What's Actually Happening: You're breaking up. That's what's happening. Someone probably told you it would take about 3 months to knock this thing out, so you started back in October just to give yourself some time. You had been dating for 3 months then, so now you're running up on 7 months. You look at the belt. You still have AT LEAST 5 months of hand-destroying needlepoint to go. Do you really like this guy that much? Maybe you do, maybe you don't, but you HAVE noticed that his holiday binge and penchant for late night fried food have added an inch or two to his waist, so even if you finish this God-forsaken icon of preppy fashion, it might not fit. Why not just let the needlepoint masters from Smathers & Branson handle it?

1. A Subscription to Netflix


What You Think You're Doing: "I'll give Catelyn a subscription to Netflix so we can watch at her place since she has a single room and I have 3 roommates who never leave."

What's Actually Happening: Your transparent attempt to build-in a booty call at your girlfriend's place has been noted. Maybe it'll pay off. But you've also just guaranteed that her friends will start mooching off her subscription, thus negating your intentions. You also just made a nice little setup for the next guy she dates after she dumps you for being so transparent. WOMP WOMP.

Happy Valentine's Day, everyone!



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  • Author image
    Patrick Simmons Harrigan: February 14, 2019

    On the other hand , a pair of Stubbs & Wooten hoes or Belgian Loafers 👞 has always been a great change from all weather SPERRY…after you have made V.D. Mistakes!

  • Author image
    Hannah: February 13, 2019

    Thank you for sharing the needlepoint belt wisdom!!!! Seriously, ladies, take note. An old coworker of mine needlepointed a belt for her bf and 1) it was too small 2) it took her months and months and 3) lo and behold they broke up shortly thereafter.
    Maybe just don’t buy your college bf belts in general.
    And unpopular opinion stop painting coolers for non-bfs. Takes too damn long and you’ll get pissed when other girls take yeti butt pics on them a week after the formal.

    Ok bye!!

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