The Winston Box: #review

I don’t usually do disclaimers, but let’s put this front and center: This isn’t any kind of sponsorship/influencer thing. They aren’t paying me, and I bought my clothes like everybody else.

A couple of weeks ago I became aware of The Winston Box. You’ve probably heard of similar services; this is one of those subscription box thingies where every so often at an interval of your choosing they send you what is effectively a blind box with some clothes that they picked out for you. You specify a few options regarding color and style choices and then you’re basically rolling dice. The hook with these guys is that they specialize in big and tall sizes. As someone who has sized himself out of entire stores– more of them than I care to admit, frankly– this was attractive. There’s a Fat Man Store out by the mall where I buy clothes from periodically, and they’ve got nice stuff but they’re expensive as hell— think $25 for a plain T-shirt, $75 for a sweater level– and the idea of a $75 box that would include two or three items that were likely to fit me seemed like it might be worth a shot.

Plus, and I cannot emphasize this enough, coronavirus. I’m pretty sure I just got involved in this because of my seething need for novelty and entertainment. So, fuck it, here’s $75; send me some shit.

This is why I was so mad at FedEx yesterday, by the way.

So that’s my box. It looked a little on the small side at first, until I thought about just how little space clothing takes up when it’s vacuum-packed. As it turned out, there was plenty in there. But hell, let’s open this thing!

Okay, I admit it: a lavender winter hat as the first item out of the box did not excite me, both because we had damn well better be well out of winter hat weather until next November and … yeah, lavender hats aren’t really my thing? But this was my first box, and they let me know there would be some extra stuff in the first box. So okay, Becky can wear the branded winter hat. I mean, it felt soft and warm, and all that. I’m sure it’s a fine hat.

I figured out pretty quickly that taking pictures of stuff in the bags wasn’t very interesting, so everything else is unpacked, in the order it was in the box:

ITEM THE FIRST! This t-shirt, featuring a vaguely phallic, vaguely Mesoamerican dude. I mean, I wear t-shirts. Like, all the time. I’m not over the moon about this one but I’ll wear it.

Now, this item, on the other hand:

homer drool dot gif, y’all. I will wear this. I will wear this a lot. It fits great and it’s super comfortable and it’s absolutely something I would have picked out for myself. I’m actually kind of mad that we’re moving out of hoodie weather for the year right now, but I expect to live in this thing for the rest of the weekend. Thumbs up A+ will wear. Honestly, this all by itself convinced me to stick around for the next box, because this would have been $100 at the fat man store, easy.

And then there’s Item Four:


At first glance, this was a huge no. One, I don’t wear sweatpants. I have one pair of what I think of as Comfy Pants(*) that I sleep in when it’s really cold, but I don’t even wear sweats around the house. Two, and it took my wife pointing this out for me to realize it, but I have very different rules for colors in shirts than I do for pants. I have at least two shirts very similar to this color, and I wear them as often as anything else I own. All of my pants? Jeans, except for the shorts I wear to bed, which are black.

These are sweatpants and they are baby blue. They are never going to get worn outside the house under any circumstances and I’m really not the laze around in sweatpants guy. Even when I’m lazing about the house, I do it in jeans.

Then I touched them, and … yeah, okay, I’ll sleep in these tonight and see how I feel. I’m a little concerned about the size, since I feel like my waist and inseam measurements for jeans are going to be massively oversized for something with an elastic waistband, but I’ll find out tonight, I suppose. Also, they had a $75 price tag on them, which, again, was the cost of the entire box.

So, one thing I’ll wear constantly and already love, one thing I’ll wear but am kind of meh about stylistically, one thing I immediately gave to my wife, and To Be Determined. Fuck it, bring on Box #2 in a couple of months.

(*) What makes them Comfy Pants and not Sweat Pants? No cuffs at the ankles. I dunno why that makes a difference to me but it does.

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Luther M. Siler

Teacher, writer of words, and local curmudgeon. Enthusiastically profane. Occasionally hostile.

One thought on “The Winston Box: #review

  1. I’m really glad to know about this – I get a subscription box of clothes occasionally but the ones I get don’t have options for men so my husband has been feeling left out. 🙂


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