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What to Buy for Your Schlubby Work-From-Home Boyfriend

Clothes nice enough to go outside in, but comfortable enough to wear all day indoors.

Collage of T-shirts and Shoes

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There are men who couldn't care less about what they wear and how they look. And then there are the people — the girlfriends, wives, boyfriends, husbands, moms, dads, siblings, and friends — who have to go out in the world with this person. Here, we're taking on the role of stylist to help someone — in this case, our own senior editor Meredith Haggerty — who has some thoughts about how her significant other dresses.

All the while taking into consideration the preferences and lifestyle of her work-from-home type boyfriend, writer Andy Hoover.

Meredith on How Andy Dresses

I don’t want to say that my boyfriend Andy doesn’t dress well. But I am more than happy to say he doesn’t shop well. How can you do something well if you don’t do it at all? You miss 100 percent of the shirts you don’t take, as they say.

In July, we went on vacation to Big Sur, and I found pieces of foam from inside his sneakers shedding around the Airbnb. He has not yet gotten new sneakers. Recently we went to Vermont, where it was snowing. I assume his feet were very cold.

Andy has some nice pieces, but they’re all gifts. From me, from his sisters, his friends, his parents. He has one great tuxedo that we don’t get quite enough use out of (has it been worn at least one place it shouldn’t have been? Yup), but for the most part his wardrobe is a lot of old T-shirts from plays or groups he was in and a couple of pairs of khaki pants of indeterminate age and that’s it, end of list.

He used to have a tan-colored Members Only jacket with a lot of holes in it, but after he wore it with khaki pants and a beige corduroy shirt, my amazing burns (mostly about him looking like the crayon a kindergartener would use to color in white people) became so hot that he had to get rid of the jacket, which was metaphorically singed. He has not gotten a replacement jacket.

Andy on How Andy Dresses

She's right! I don't shop. I don't really see the point. I work from home, I slouch around Brooklyn; these are my days. I prioritize comfort, mostly, with ease a close second. All that said, I don't mind looking good. I just wish other folks would do the thinking for me.

I grew up near an enormous shopping mall. Between my childhood home and the mall there are these woods, and a major highway. I guess I'd rank my comfort wandering those spaces something like: 1) Woods; 2) Enormous Shopping Mall; 3) Major Highway. So it's not like I don't like shopping at all. I definitively enjoy it more than standing on or near a major highway. I just am easily overwhelmed, and don't generally know what to look for, and if you have two pairs of jeans you truly value I don't entirely understand why you would really need a third. (Don't get me started on wearing pant types other than jeans.)

Clothes exist to be worn until they are unwearable. You then thank them for their service and, if you listen very carefully, you can hear them thank you back for all the hard work you put in them, for your resolute willingness to see them worn to their very extremity. Seams exist to be frayed. Most of my zippers, including some central to public decency, have grown slack and indifferent in their old age, their crooked lines of metal teeth like roommates who despise one another. I have way too many T-shirts because there was a time in my life when I was involved in many non-paying endeavors whose end result was: T-shirt. I treasure my socks that actually match, as who can know the hour when one is summoned to a formal affair. You need to be ready for anything, for a cotillion, even (I am not ready for a cotillion).

I am, in short, a mess, but I comfort myself with the knowledge that I am confident in my life choices and have bolstered my savings via prudent investment in not-clothes. In the event of a nuclear war, my sartorial losses will be relatively mild, and it's with this knowledge that I warm myself at night, along with whatever mismatched rags the fates have brought me that day.

Cam on How Andy Can/Should Dress

I worked at home myself for a decent amount of time and often fell into the trap of wearing my most comfortable and unappealing items.

But the comfort never seemed worth it once my girlfriend came home to me wearing the same thing I was in when she left for work that morning. The obvious answer here is a pair of fancy tailored sweatpants. Even Uniqlo makes nice ones for $29.90 now. But if you’re really a pants purist, stretchy selvedge denim (also offered for just $49.90 by Uniqlo) is about as comfortable as jeans get.

Also, there are way too many options for classic, stylish, and affordable shoes out there for you to keep wearing ones with holes in the bottom: Vans’s low-top Eras ($60) or slip-ons ($60) in a more grown-up color; Converse’s Chuck Taylors ($55) or Jack Purcells ($95); Clarks’s Desert Boots ($130); or Doc Martens’s classic Three-Eye Smooth shoe ($105) or Chelsea Boots ($130). That’s about as painless as the bottom half gets — not even once did we have to stand in the middle of a freeway.

Fashion has taken to the logo, so there's no need to completely give up the style of the old T-shirts you've grown fond of. Todd Snyder’s Champion collab immediately comes to mind — especially the Printed Mélange Cotton-Jersey T-shirt ($75) — as does Saturdays Surf NYC and its Printed Cotton-Jersey T-shirt ($40), and this A.P.C. College Shirt ($110).

If you want to get nice plain T-shirts, check these places, organized from most to least affordable: Uniqlo (as low as $6), Everlane (as low as $16), and Unis (as low as $52). Somehow, a black T-shirt has the ability to look great and nice dinner-ready even if you’ve just been podcasting from home all day.