The Best Men’s Clothing Subscription Boxes of 2020 to Build Out Your Wardrobe

Google “men’s clothing subscription boxes” and you’ll find no shortage of options. Style subscriptions like Trunk Club helped to make these box delivery systems a thing a decade ago, and there are now roughly as many mail-order menswear services as there are podcasts for them to advertise on. All of them offer roughly the same deal: you fill out an uncomfortably probing questionnaire about your lifestyle and body shape and spending habits; a stylist or algorithm or some combination of the two selects a crateful of items suited to your tastes; and, finally, you’re only charged for the items you decide to keep. Easy-peasy, right?

Here’s the thing: if you’re even a semi-regular reader of this magazine—if you come to us to read up on hot sneaker drops, or the waviest new labels to check out, or whatever’s popping off in Paris right now—these men’s clothing subscription boxes are probably not for you. That is, they aren’t really for anyone who already considers themselves to have a discernible sense of style, or is actively working towards developing one. There are no wild grails to be found within their thoughtfully-designed cardboard confines.

What you will get—in the best of these boxes, at least—are a bunch of rock-solid foundational basics, the kind of clothes you can build an honest-to-goodness wardrobe around. If you hate shopping with an absolute passion but still need to look somewhat presentable, these services will be your jam. If you earnestly want to start dressing better and have zero idea where to start…well, buy a subscription to GQ…and then maybe consider signing up for one of these boxes, too. And sure, if you’re really into fashion you might occasionally receive something in a subscription box that you love and might not have considered otherwise—but it’s probably still safer to just shop for yourself and pick out stuff you’ll definitely like.

In any case, we spent months testing the patience and limits of our office mail department by signing up for as many of these style subscriptions as we could. Here are our thoughts on the cream of the crop—and a few on the not-so-awesome ones, too.

The New Kid on the Block: Personal Shopper by Prime Wardrobe

Amazon’s menswear offerings are getting better all the time, but actually navigating those offerings on the Everything Store’s often chaotic user interface is a whole other story. That’s where their newly-launched Personal Shopper by Prime Wardrobe service comes in: for just $5 a month, you’ll get a boxful of the choicest bits on Amazon—from brands like Lacoste, Calvin Klein, and Adidas, among others—all curated to your tastes, needs, and budget. You’ll have a week to try on the eight items in your box. 

Given exactly how much the Bezos Empire has to offer, there’s plenty of opportunity to get hyper-specific with your choices and leave your stylist notes along the way. Got a job interview or outdoor wedding coming up? They’ll sort you out. Need some performance activewear or rugged outdoors gear to go with your new hiking obsession? All that’s available, too.

Personal Shopper is exclusively available to Amazon Prime members. If you’re not currently a Prime subscriber, you can sign up for a free 30-day trial—just in time for Amazon Prime Day.

Price: $5 flat fee per month, in addition to the cost of your Prime membership.

The Best All-Around Style Subscription Box: Trunk Club

Trunk Club has one major leg up on its competition: it’s owned by Nordstrom, which means it has access to the hundreds of designers the department chain carries. Couple that with an attentive personal stylist—we were paired with Brianne, who asked us a few clarifying questions about how and when we’d use these clothes and how much we were willing to spend—and you wind up with a box full of totally wearable, reasonably stylish stuff from labels you actually recognize. In our case, that meant a hardy Carhartt WIP chore coat, a Nike windbreaker, a couple of Rag & Bone tees, socks and underwear from Polo, AG jeans, and a whole lot more.

Beyond the range of available goods, the service’s best feature is its flexibility: you can order trunks one at a time, schedule a few in advance, or keep ‘em coming indefinitely, all for just a $25 styling fee per box that gets waived as long as the items you keep total more than that amount.

The problem, of course, is that name-brand clothes come with name-brand prices. Had we opted to keep all 15 items in our trunk, it would’ve cost us just over $2,000. That’s a pretty penny for what amounts to roughly a week or two’s worth of looks. But if you’re just looking to add a solid piece or two to your wardrobe every once in awhile—an AllSaints denim jacket, say, or a chill navy camp shirt—without the hassle of having to go out and actually shop for yourself, Trunk Club is probably your best bet.

Price: $25 styling fee per box, which will be applied towards any items you choose to keep.

The Best Brand Loyalist Box: Frank And Oak Style Plan

If you’re the kind of dude who likes to find a brand that really works for him and stick to it⁠ religiously—and if that brand happens to be Frank And Oak⁠—then have we got the subscription box for you. The Montreal label’s recently-launched Style Plan sends you a crateful of their affordable, hip-adjacent duds each month, selected for you based on your stated preferences via a mix of an algorithm and a real-life stylist. You’ll get all of the items in your box at a discount (up to 20% off retail), and you won’t be charged a styling fee unless you choose to return everything.

Frank And Oak’s clothes tend to look best on younger, leaner folks who work in offices with high ceilings and lots of free snacks. That is to say: expect a whole lot of trim chinos, oversized tees, patterned button-downs, and Vans Old Skools—the kind of wardrobe you’d come across during a stock photo search for “millennials.” It’s a specific look, sure, but the stuff is all pretty well-made for the price, so if it works for you and fits you well, this is a great option.

Price: $25 styling fee per box, which will be applied towards any items you choose to keep.

The Budget Option: Menlo Club

For a flat rate of $60 a month, Menlo Club will send you a couple of items from their roster of in-house labels—the best known of which is New Republic, the shoemaker behind some of our fave sub-$100 Chelsea boots and white sneakers. Beyond the rock-solid footwear, expect to find some trendier bits (like a camo rugby shirt or cropped cargo cords) and style-forward-ish activewear in the mix. This is stuff you probably won’t wear all the time and definitely won’t own forever, but might do the trick if you’re looking for an affordable way to freshen up your fit rotation once a month. One thing worth noting, though: Menlo Club doesn’t do returns (though you can exchange items for size), so what you get is what you keep.

Price: $60 a month for a package of two to three items.

The Other Contenders: Stitch Fix and Bombfell

Stitch Fix and Bombfell are two more subscription services that work on the same basic model as the rest: fill out a form, work with a stylist, receive a box of clothes, pay a $20 styling fee that gets applied toward anything you choose to keep. The stuff they sent us was…totally fine. Solid. Maybe a little dad-ish—and not necessarily in the cool way. They each serve up a mix of low-to-midrange brands you’ve seen in malls (Original Penguin, Jack & Jones, Tommy Bahama) and a few generically-named ones you haven’t (7Diamonds, Hawker Rye). They’re totally workable options if you aren’t really looking to push any boundaries with your style and just need clothes for clothes’ sake. But for just a little more dough, we’d probably choose Trunk Club over either of these any day of the week.

Stitch Fix Price: $20 styling fee per box, which will be applied towards any items you choose to keep. If you decide to keep everything, you’ll receive 25% off the entire box.

Bombfell Price: $20 styling fee per box, which will be applied toward any items you choose to keep. If you choose to keep four or more items in a box, you’ll get 20% off your purchase; 15% off for three items; and 10% off for two.

The Shameless Plug: GQ Best Stuff Box

OK, OK: our quarterly Best Stuff Box isn’t strictly a clothing subscription service. It’s better! For a mere $50 (or even less if you buy a year’s supply), we pack in well over $200 worth of our editors’ go-to style, grooming, and lifestyle products for the season. For summertime, that means a killer pair of shades, a mineral-enriched natural deodorant, a next-level toothbrush, and way, way more. Sign up and let us make your life a little cooler and more stylish—one crate at a time.

Price: $50 per box, or $190 for four.

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