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How to Shop for Hard-to-Buy-For People

Haley, 27, is on the hunt for 32I bras for herself and gifts for her family that won’t get returned.

An illustration of a coin being dropped into a piggy bank.

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Welcome to Racked’s How Do You Shop? series, in which we ask a variety of people some deeply personal questions about how they earn, save, and especially spend their money. If you know or are someone with an interesting relationship to $$$, email

This week, we spoke with Haley Houseman, 27, who lives outside of Boston and works as a freelance writer and illustrator, as well as a community manager at an astrology startup. She’s been doing a lot of shopping for herself, since she recently changed clothing sizes, and also for her partner and family as the holiday season looms.

What’s your annual salary?

My annual income for this year is close to $40,000, from a mixture of freelancing and temp jobs. I have a new salary, which is $48,000, but I didn’t start that salary until October. I was making between $25,000 and $30,000 before this year, so it’s a big step up for me.

What’s your rent?

I pay half of our $1,450 rent, so $775.

How much do you tend to spend on yourself when shopping each month?

For skincare, I spend, like, $50 a month. For clothes, I actually recently had a wardrobe revamp because I went up a couple sizes, so my spend is a lot more than it usually would be. But I would say that I usually average between $150 to $200 a month.

Let’s talk skincare!

Like everybody else on the internet, I use The Ordinary. I’d been using rose hip seed oil from a really expensive herbalist-type place for a long time for a scar on my leg, and I eventually started using it for everything, so I was thrilled when The Ordinary came out with a cheap option [about $10]. I used to pay, like, $25 for a similarly sized bottle.

So I use that, and then most of my other skincare products that I use every day are Dr. Jart. My regular cleanser is the DermaClear microgel, and then I use the Tiger Grass cream. But I got really into skincare and kind of ruined my skin in my excitement, so I scaled it way back.

The Ordinary Rose Hip Seed Oil, $9.80

My boyfriend is very much a “rub some dirt on it” kind of dude. But I have a lot more success offering him an exfoliator or something from Dr. Jart, and I think part of it is that it’s super unisex in the packaging; I noticed that in the past year or two, all of the trendy packaging has become blues and greens, sans-serif, downplaying the luxury aspect, and really playing up that “medical” look. I think we’re all looking for an excuse to pamper ourselves right now, because things are kind of rough.

So now let’s talk clothes — you mentioned that you’d recently gone up a couple of sizes.

For a very long time I’d had a perfect hourglass size 8, and I was really busty, which meant that as a teen, before we had all these great in-betweener-sized brands that people do now, I wore a ton of vintage because I could fit really neatly into those pencil wiggle dresses and stuff. Which was great, but I can’t fit into that stuff anymore. I loved getting rid of all of it.

Now, my body looks different in clothes. It took me a while to figure out what actually fit, and what I wanted to fit. So there was a lot of buying and returning while I figured out what cuts now look better on me. My bra size went up out of proportion to my actual dress size. I’m now a 32I! I’m a lingerie enthusiast, so I have plenty of places to buy it. But I can’t wear crop tops anymore because crop tops are just like nipple bibs on me. Like, I had to scratch whole things that had made part of my look and could no longer be part of my look.

What brands do you find yourself going back to again and again?

I wear a mix of ASOS, Everlane, and & Other Stories. I’m also trying to buy a little bit more ethical fashion, as opposed to fast fashion, but I couldn’t quite afford to revamp my whole wardrobe that way. Everlane for me is pretty hit-or-miss in terms of whether or not I’m gonna be able to size myself into them. I used to love American Apparel, but they’ve scaled way back now. I still do try to do a little bit of vintage shopping, but I’m just not a size that people were back in the day.

What about lingerie?

So I was a DD cup in fifth grade. (And, like, retroactively, a DD is not that big, because now we all are much more focused on bra fitting, and that’s actually not that big of a cup size.) But I just started being into lingerie very early. If I wanted something to hold my breasts up and actually be comfortable and not give me any pain — it’s much more of a concern when they get that big. You just really want them to stay put!

But I really love pretty lingerie. My favorite brands are Fortnight, Playful Promises, and Lonely (which doesn’t make bras my size, but I like their panties). The big aggregator site that I use is Journelle. And when people are getting into underwear, I’m always like, “Go to a Journelle store if you can, get fitted by a real person. Either get fitted by the elderly woman who runs the bra shop in the strip mall, or go to Journelle. Don’t go to Victoria’s Secret. Get somebody who’s gonna use a tape measurer.” I also love everything about the blog The Lingerie Addict.

Let’s talk about shopping for other people, since this is the time of year when folks are thinking about buying gifts.

Usually, I buy my Christmas gifts over the course of the year. But it’s been kind of a crazy year for me, and so I did not do that. What I am doing this year is getting people stuff specifically that I know that they want to replace but never get around to it. Like, my dad is really particular, so I found the exact vintage briefcase that he used but isn’t as worn to shreds, and just got that.

As for my partner and I, we’ve been together a really long time. We’ve been together for 12 years. So this year, I finally caved and got him to make a wishlist of things that he might want to get for himself. He’s a musician, and he wanted some very specific sheet music, stuff that I wouldn’t want. My big philosophy is not to be shy about asking people what they want.

When I ask them, like, “What do you really want? Is there anything you’re really excited about?” very rarely are people like, “Oh, no, there’s nothing.” And those people are hard. My mother does that to me — she’s also very hard to buy for. I always keep the receipt and I put it in the card. And I say, “Okay, if this isn't the thing, we’ll go back and we’ll buy you something you like. We’ll go shopping together.” But she loves to shop, so she’s equally into the idea of going to the store with me. Whereas my little brother is not, and so he gets Mario Kart.

Growing up, Christmas was mostly about the family and the connection, and we did a lot of familial travel. As we got older, that stuff changed, as it does. And for a couple of years, it was all about the presents, and somebody always ended up crying. It was always like, someone didn’t get exactly what they wanted or blah, blah, blah. Often, I would get really worked up over trying to make everything perfect and then have a meltdown. So a couple years ago, we actually made a family edict that everybody does one gift, especially now that we’re all older.

You get one shot. We spend most of the holiday eating. My partner is from the same hometown as a lot of our mutual friends, and so we spend a lot of the holiday like it’s not really about the presents anymore. We spend a lot of it bopping from house to house; we do a cookie swap in the neighborhood, where we make trays of cookies for every neighbor on the street and stuff. So I’m really grateful that it’s not all about the presents, because it takes the pressure way off.

And this is an adult choice that my partner and I made when we moved in together: We set a $100 limit on presents. It’s the total budget for everything. So if you want to go all out and buy a $100 gift, that’s stuff that you do. And if somebody wants a $100 gift, then you know that, and that’s cool, but we usually do a mix of little stocking-stuffer type things and bigger stuff.

Any other advice?

Everlane Day Heel, $145

I’m really obsessive about planning my purchases ahead of time, especially for stuff for me. It sounds so nerdy now saying it, but I try really hard to do a lot of research about what I want to look like and then keep my eye out for pieces. I organize on Pinterest, and I try to wait a couple of months if there’s a piece that I really want. Like, I wanted the Everlane Day Heel, but I probably waited six or seven months to pull the trigger on that, and I waited until I had stuff I knew I could wear with it and I knew exactly what I wanted it to look like. Something is always gonna come back into stock. It’s very rare that something is gone forever.