rabbit hole

A Deep Dive to Find the Right Faux–Boxer Shorts

Photo-Illustration: by The Cut; Photo: Retailer

Lewis Carroll first coined the term “rabbit hole” in the opening chapter of Alice’s Adventures in Wonderland, referring to the strange and lengthy journey Alice takes after following a rabbit into a burrow that ultimately leads them to Wonderland. Strange and lengthy happen to be fitting descriptors for how I shop. Each and every one of my shopping rabbit holes is entirely self-inflicted — the result of becoming obsessed with something niche or particular that I have to find and not relenting until I do (or at least come close).

I thought it would be interesting to start bringing some of my rabbit holes out into the open — a voyeuristic peek inside my digital underwear drawer (or rather, my laptop search history). Maybe you happen to be looking for the same hyperspecific thing, or maybe you’re interested in seeing how I poke around the dusty corners of Google, Etsy, eBay, and the RealReal. Let’s jump in, shall we?

Origin Story | Criteria | Rabbit Hole | Winner

Searching for:

The perfect pair of boxer shorts that aren’t actually boxer shorts.


The Origin Story

Faux–boxer shorts (i.e., boxer shorts that are intended as outerwear instead of underwear) are a dime a dozen these days. At first glance, I understand why this search might not seem very specific, but it is, because I’ve got some pretty stringent criteria.



  • Look distinctly more like outerwear than undergarments
  • On the shorter side (higher than the middle of my leg) and flaring out slightly on the sides
  • A soft, comfortable, and very flat elastic waistband
  • Lightweight but not flimsy or see-through
  • High-waisted (hitting right above my belly button)
  • 100 percent cotton.


The Rabbit Hole

First Step: Google Photos Is Your Friend

Before it shut down, Entireworld created the perfect pair of faux–boxer shorts. I own a single pair and rue the day that I didn’t buy them in every color. I used these shorts as my first reference.

When I have a photo of something I’m looking for, my usual first stop is the Google Photos app. A friend told me about it last year, and it has been life-changing. You upload a photo, and after analyzing it, the app will either tell you exactly what it is and where you can buy it or show you a small selection of very similar search results.

I uploaded a photo of my beloved Entireworld shorts and was delighted when the app accurately identified them and served up a few promising Poshmark and the RealReal hits. Unfortunately, my excitement was short-lived, because all of them were either sold out or not in my size.

After striking out on the exact hits, I started analyzing the “similar” search results. Keeping in mind all of my criteria and weeding out the shorts that only came in toddler sizes (there are lots of those), the following looked like the most promising.

I liked Everlane’s seersucker boxer shorts at first glance because of their great colors and 99 percent cotton, but they weren’t quite what I was looking for. I wanted them a couple inches shorter, slightly flared out, and sans drawstring.

For Days’ Poplin pull-on shorts got points for no drawstring, but they seemed too long for me and didn’t have the right silhouette.

These objectively cute Faithfull shorts are on sale here and here. For me, though, they were a tad long.

Second Step: Look for Secondhand Options

Secondhand boxers might be questionable, but my search led me to the following pairs.

The RealReal always features on my rabbit-hole journeys, because even though it can be hit or miss, when it hits, it hits. In this case, it was more of a miss, unfortunately. I found this great Caroline Constas pair that checked a lot of my boxes, but it isn’t my size.

I hightailed it over to Etsy, where I found some incredible pairs of vintage men’s Jockey boxers from the ’80s in three different shades of blue stripes. It looks like they have an open fly, but in this case, exceptions should be made, because they’re just too good. Plus the stitching is very subtle, and I’m sure you can easily have it sewn shut by your local tailor. (These weren’t my size either.)

Third Step: Choose Three Key Words

I had a brief eureka moment when I saw that one of the Etsy descriptions referred to a hem as “scalloped.” I tried using it as a key word, but as you might expect, it kept leading me to stuff like this, which is cute but not the objective. Undeterred, I decided to text my friend Claudia, a professional clothing designer, and ask if there was a “professional clothing-designer name” for this type of hem that would be more helpful. Genius that she is, she responded, “It’s called a dolphin hem.” Never in a million years would I have come up with that. It was key-word gold. I typed “dolphin hem cotton shorts” into Google and found these.

The Tech Dolphin Shorts from Tilley aren’t boxer-adjacent (or reasonably priced), but they’re the perfect length and silhouette, and I love the khaki-green color, so I’m keeping an eye on them to see if they go on sale.

The key word “cotton track shorts” led to these. They’re cute, but they look too much like underwear.


The Winner

I ended up buying the shorts below.

I’ve already worn these a few times this summer, and they fulfill almost all of my criteria. My only wish is that the dolphin hem slanted up and kicked out a little more aggressively, but otherwise, they’re pretty perfect. I like them a lot and have zero regrets.

That said, I’ve got saved searches on Poshmark and the RealReal in hopes of locating a pair of my favorite Entireworld boxers in my size. Down the rabbit hole I go again.

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A Deep Dive to Find the Right Faux–Boxer Shorts