The Annual Tomboy’s Guide: How To Gift Him Right

Ladies, who here finds gifting the men in your life confusing? I get it: the one-word answers, football season tunnel vision, and overall boredom surrounding shopping for the holidays. How do you shop for a guy with such limited communication on what they want? It seems like a code we should be able to crack through careful analysis. However, the answer is much MUCH easier than you think. It’s why I started this series three years ago, to help each of you gain a greater understanding of how simple men can actually be when it comes to gifting. I’m exposing the guys… Welcome to this year’s iteration from your fave “bruh” girl: the annual tomboy’s guide on how to gift the men in your life!

How to gift the men in your life: The Rules of Engagement

I’ve gone over recommendations the past few years, but what’s the secret sauce? This year, I’m sharing the pillars of my strategy. “This is not ‘Nam, THERE ARE RULES!” Just like Walter says in The Big Lebowski, there are rules we must abide by when it comes to how to gift the men in your life. Surprisingly, they’re not as restrictive as you might think. With a little finesse, you can tailor them around any man you might be gifting this season, regardless of their personality or sexual orientation.

  1. Stay away from large expensive purchases. Unless you’re on that level of understanding with them, it’s not a good idea. Yeah, they may be talking about investing in their first pair of skis or Gucci loafers, but let them be the one to buy it. Guys love fulfilling these purchases themselves, let them have their moment, they know what they want more than you will. Don’t believe me? Think how annoying it is when a guy buys you an expensive piece of clothing or jewelry you hate. We all saw it with Carrie and the Judith Leiber purse.
  2. Aim to complement their daily lives or biggest hobbies with your gift. Guys appreciate it when you can really see who they are at the core.
  3. Solve a problem with your gift. Guys are simple. Help them with a daily struggle. They will appreciate it so much more.
  4. Consider experiences instead of tangible items. Every guy loves an element of adventure.
The 2020 UNOFFICIAL Edit
The In Laws + Your Boss

Holiday parties can be stressful if you aren’t sure how to gift the host. I’m looping my preview into in-laws to this post since there is a male party involved. I like to elevate basic needs for these types: it’s a way to make their daily life easier with a bit of elegance and thoughtfulness. I’ve given a few of these in the past, and some for this year:


Close Friends

The easiest way to make your gift a hit? Aim for indulgence. We know our friends best, play to the opposite of whatever it is they love most. Yes, this is counterintuitive: what would they lust about binging on after a workout? What would they love to come home to after a stressful day at the office? These play:


Significant Others

This can be a tricky thing, especially if you’re a new couple. I personally love gifting experiences in this case. It allows you to bond doing something exciting together: something every guy will appreciate. Top it off with a small gift in the meantime that plays into their current life and interests. Some of my tried and true hits:

For more recommendations and tips on how to gift the men in your life, head to my former post and/or 2017’s original post: I’ve given them the 2020 twist!

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Photography by Mari Uchida 


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