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Leandra and Harling Try to Figure Out Which Gifts to Get Their Partners

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What Would You Wear With This?, heir to the throne of Should I Buy This?, is a monthly conversation between Leandra and Harling about the contents of their online shopping carts and the potential outfits that lie within. Come for the clothes, stay for the feelings.


On Tue, Dec 3, 2019 at 10:08 AM Leandra wrote:

What’re you getting Austin for the holidays? I am uniquely unskilled at giving gifts to Abie. I’ve never been good at getting stuff for guys, which is weird given that I have three brothers. Do you have, like, a formula that helps you figure out what to get for Austin?

On Tue, Dec 3, 2019 at 11:04 AM Harling wrote:

Does Abie shop a lot for himself? Austin rarely does, except to buy something he really *needs* and in that case it’s usually a carbon copy replacement of something that has worn out after many uses. Ergo, when I’m brainstorming gift ideas for him, I try to think of things that ascribe to the following criteria:

1. Something he doesn’t necessarily need (because he has that area pretty much covered) but might want and/or enjoy in ways that extend beyond simple functionality

2. Something that I would personally take pleasure in seeing him use and/or wear often (the selfish part of the selflessness that is gift-giving?)

One of my best “hits” in the gift arena to-date that checks both of these boxes was a pair of shearling-lined suede slippers, which are a significantly softer and more aesthetically-pleasing upgrade from the college-era moccasins he used to wear. Another good one was a nice-looking raincoat. This Christmas, I’m looking to make a similar kind of upgrade vis-a-vis the sweatpant joggers that he always wears on airplanes. I don’t love the ones he currently has because they have a weird zipper in the back and a huge logo on the front. They put too much emphasis on the ath element in athleisure and I want to get him an alternative option that feels… dapper? stylish?… in addition to comfortable, thus fulfilling both points of criteria because he (conceivably) wants to look good and feel good and I love to witness these objectives come to fruition together. Few things are more satisfying than airport attire that can do both.

Joggers I’m eyeing include: these from Aime Leon Dore (I’m planning to stop by the store to check them out in person sometime this week) and these from Outdoor Voices.

What are you thinking about for Abie? You could always ask Madelaur to make him a pasta necklace.

On Tue, Dec 3, 2019 at 4:23 PM Leandra wrote:

Oh that’s a smart strategy! Get him a thing within a category you know he uses, but make it a more enhanced version of that thing.

Abie is just so specific about his STUFF. I hated this pair of Rag and Bone sneaker-boot-things that he used to wear, so I got him a navy blue suede pair from a fancy store on the Upper East Side to replace them, but they were half a size too big and he is such a stickler for comfort which is honestly an experience I cannot empathize with so he never wears them. He mostly wears an Outdoor Voices fleece with joggers (actually the ones you sent) and Spalwart sneakers now. I wish he’d wear skinny khakis, brown suede monk straps, and cable-knit crewnecks. That seems like a far stretch from his current fare, but maybe a good in-between could still apply the joggers, modify the fleece to, like, a cardigan a la this.

And I’m into these too!

If I were shopping for Abie as if he were me, I’d get this cardigan.

And this colorway in the sneakers.

Will Austin basically wear whatever you get him? The best gift I ever gave to Abie was a theragun for his birthday last year but in hindsight, it probably wasn’t that good a gift because he never uses it anymore….

Maybe I should just draw up like… a certificate credit for him to use the next time I have a nervous breakdown that gets him out of psychological jail free.

What are good like, non-fashion things to get a guy?

On Wed, Dec 4, 2019 at 4:23 PM Harling wrote:

Honestly IDK if Austin would wear whatever I got him because, now that I think about it, I have yet to fully test the boundaries. I would love it if he wore these sneakers with these socks, but proposing that might be the equivalent of asking him to consume ashwaganda powder: not particularly in-character. And that’s the other tricky thing about gifting!!!! Especially to a partner I think, because it’s kind of made out to be a physical manifestation of how well you understand them… right? Which is absurd, since some people are simply better at gift-giving than others and therefore more adept at expressing their understanding of partners/friends/fam in that particular way. I guess that’s why it’s a love language.

Potentially viable non-fashion ideas I’m percolating on are: a non-boring cup for desk pens, a chic humidifier, and a facial (fairly sure Austin would love if he tried but likely wouldn’t take the initiative himself so this is a humdinger option according to my aforementioned criteria). I’ve always wanted to be the type of person who is good at coming up with “experiential” gifts like concert tickets or trapeze lessons but have yet to assume this elusive identity.

Do you and your brothers exchange gifts? I have zero brothers so zero experience in that particular man-gift arena (actually, my sisters and I usually tell each other what we want with great specificity, which is kind of funny), but I’m very seriously considering getting this absurd contraption for my dad.

On Wed, Dec 4, 2019 at 5:00 PM Leandra wrote:

We don’t celebrate Christmas, so gift giving is mostly in the context of birthdays, and historically I haven’t given my brothers stuff, even though my oldest brother would be easy to shop for. He has such a distinct sense of style that is hard to miss–could basically get him anything from John Elliot or Aime Leon Dore and he’d be thrilled. I just did a quick Mr. Porter scan and this hoodie has his name all over it.

My two younger brothers are less communicative both visually and verbally about the material things they desire, so I’d be at a loss on what to give them. Though now that I think about it, I wonder if that just means I’m being lazy about actually evaluating what I know about them and their interests and using that information to suggest a gift. Overall, tho, I feel like family gift-giving has less pressure on it. With your significant other, particularly in the beginning, I feel like there’s so much pressure on getting it right because of the assumption that it indicates how well you know your person, though I’d argue that’s a flaky theory.

Do you remember the first thing you ever bought for Austin? I’m trying to think of the first thing I gave Abie and I think it was a tie, which was probably my mom’s idea, and timed with his first job offer. In hindsight it was so, so stupid because… is anyone ever excited to get a tie? Even if you need one! I also got him an orchid as a housewarming when he moved into his first apartment. He broke up with me the night I set it on his windowsill. Maybe my theory’s not that flaky….

On Thu, Dec 5, 2019 at 2:04 PM Harling wrote:

All roads lead to Rome = all lack of good guy gift ideas lead to a tie. That was the first gift I ever gave Austin, too. We were in ninth grade. It was navy with sailboats. I’m going to check his tie rack tonight to see if he still has it.

The pressure is def more acute in the beginning, even beyond tangibly demonstrating your understanding of the other person, because at that point it can also be a tangible measure of how serious you think the relationship is. And mismatched reads can easily occur—I remember one of my friends telling me that she got her boyfriend a really nice pair of loafers the first Christmas they were together and he got her a gag gift (‘Football for Dummies’). What do you think the perfect “I know we only recently started dating but it’s the holiday season and I like you” gift for a guy is? Should there be a rubric for this too?

Dating 1 month: a book of funny essays (good source of potential inside jokes)
Dating 3 months: a monogrammed airpod case (personal, but only in the most literal sense)
Dating 6 months: a vintage travel poster (from one of his favorite cities, or maybe somewhere you’ve talked about going together)
Dating 1 year: a couple’s mitten (JK, but I’m thrilled this is a thing that exists)

On Thu, Dec 5, 2019 at 2:52 PM Leandra wrote:

I’d say go broader —

Dating 1 month: A personal joke/gag gift—coming to mind is the DVD of Along Came Polly that Abie bought for me when we were dating because we both loved it (IRL I’m Jen, he’s Ben). This sets you up for a hopeful future because it’s the first inkling that you’re starting to get each other.
Dating 3 months: A useful gift—kind of like that airpod case if you know he often loses them or, like, a set of pillows if they often complain about neck pain and shit.
Dating 6 months: An experience—you’ve been together long enough that you know you like to spend time together, now do it on steroids. This could be a fancy dinner or off-Broadway show if you’re more old fashioned and won’t travel together until later into the relationship (which I wouldn’t, but mostly because I couldn’t). If you have enough $$, doing a one-night staycation at a good hotel + multiple room service meals is cozy AF and tbh probably leads to v good $ex.
Dating one year: An engagement ring for yourself. Are you fucking kidding me!? You have been the best and most thoughtful partner through all the gift milestones. It’s the least you can do.

I’ve picked some unconventional pearls (pun both intended and not).

This enamel ring
This silver band
This gold ring (but you gotta get two)
And this $100 cocktail ring.

What’s the best thing you’ve ever given Austin? I actually don’t think I feel uniquely good about anything I’ve given to Abie!! Though now that we’re talking about this, I have grand plans for his 35th!

On Mon, Dec 9, 2019 at 6:02 PM Harling wrote:

Honestly, I thought those slippers I linked earlier were the best thing I’ve ever given him because he tells me how much he likes them all the time, but now that I’m thinking about it I’m like, really? That’s all I have to show for myself 16 years into a relationship? Slippers? Idk.

I was in the midst of a lengthy subway ride over the weekend, apparently my preferred environment for potentially questionable navel-gazing, when I had a thought that instead of buying him something for Christmas this year I should write him a love letter. Have you ever written someone a love letter?? I haven’t really, unless you count the one I wrote to my parents when they let me take a semester off from college to live at home because I was having a rough time, so I feel like it could be a ripe idea in terms of a gift that is free but also pricele$s, if you know what I mean. It’s also possible I’m just projecting my own desire to receive a love letter, which I never have (this is not a hint, just the truth, but maybe I’ll combine the gift of a love letter with the gift of nice stationery to plant the seed for a response).

Also, as I’ve been typing this, a memory just resuscitated from third grade when my class did a class-wide Secret Santa, and the girl who had me cleaned out and organized the contents of my desk because she knew I was the type of person who hated doing that whereas she was the type who gets high off of Kondo-ing stuff. And I remember being DEEPLY TOUCHED, not to mention thrilled that I could actually see everything in my desk for the first time in months. So that made me think that doing something for a partner that you love doing but they dislike doing or aren’t as good at doing could be a fun gift idea, too. Like cooking them dinner, or shining all their shoes, or arranging some kind of self-care appointment on their behalf. I recently made Austin a dentist appointment and though that wasn’t his actual Christmas gift it was extremely romantic, if you ask me.

Back to stuff for a sec though: I just came across this witty shaving cream and felt an urge to PSA it as a gift idea for sand papery paramours whose make-out calling cards are beard burn.

On Tue, Dec 10, 2019 at 10:31 AM Leandra wrote:

Woah, woah, woah, you can’t just drop that semester off school bomb and not elaborate!!!!!!!!!!!!!!!!!!

I have never received a love letter either. Have always wanted a speech made on my behalf, but have similarly never received one of those. As I get older it becomes clearer that when you want something no one will give you, you have to go and get it yourself, and thus to that point it is time to write yourself a love letter, Harling Ross. Also becoming clearer with age: it is the thought that counts. Your secret Santa gift sounds like exactly the kind of gesture that sticks. Last year I publicly recommended getting your busiest friend two glasses, a bottle of wine (but now that we’re in the era of sober-curiosity, maybe I meant Seedlip, or, if you’re committed to being medium, the artist formerly known as moderate in 2020, Haus–“the Warby Parker of aperitif”) and a block on their calendar. Amelia did that for me and it was my favorite 30th birthday gift.

Feel like our parents’ generation truly was all about the STUFF. Diamonds represent commitment! Jewelry IS the thought that counts! And I know I’m just reiterating what the market has been reflecting for a while now, but that really has changed, huh? But in the interest of being medium, I do like the thought of a gesture that comes with a physical talisman, if only because it serves a signal to remind you of the former. To that point, how about this to accompany a note to Austin every day for the first half of 2020 with the caveat that he reciprocates for the second half?

Now back to that year off school, HARLING.

On Tue, Dec 10, 2019 at 1:46 PM Harling wrote:

Oops, I’m about to REALLY derail this convo about gifts for partners… because the school thing is rather somber and not at all gift-related… but the reason it came to mind is probably because I’ve been thinking a lot about that time in my life recently, for whatever reason things in our past choose to booby trap the present. I don’t talk about my semester off much–not because I’m hiding it, but because it was so long ago and it doesn’t really come up. Except in conversations about holiday gifting, I guess!!!

Anyway, I started college unwell but pretending everything was fine because that seems to be my default coping mechanism, for better or for worse. I had an eating disorder that eventually linked elbows with a bad case of depression since it was impeding my social life to such a significant extent, and that combination became unbearable at a certain point in the middle of my sophomore year, so I took a medical leave and lived at home with my parents for the rest of the semester while I got treatment (hence my love letter thanking them). I went back to school the following semester in better mental shape, but the whole thing still reverberated throughout my college experience in ways that remain tender whenever I think about them. I feel like I was robbed of a lot of the experiences I wanted and imagined, and the only thief I can really blame is myself.

Like I said, kind of somber relative to holiday gifting, but I’m pretty sure the worst years of our lives are the ones that manufacture our greatest reserves of empathy. Maybe writing that down is my self-penned love letter for today.

That gift c/o Amelia is genius. My friend made a very low-key dinner reservation for just the two of us a few days before my bday last year and surprised me by footing the bill. It was my favorite gift. I do think our generation cares less about STUFF and more about quality time (sushi making class, anyone??) and/or words of affirmation (let’s restore the good name of romantic Post-It notes post-SATC season 6 episode 7). Do you think it’s because social media has placed more of a premium on those things, particularly the quality time piece, because time is more valuable than ever now? Could be a cynical take, but I don’t necessarily think our generation is less materialistic, just that the nature of the material we covet has changed. I still think you should get Abie these monk strap shoes, though.

On Tue, Dec 10, 2019 at 4:41 PM Leandra wrote:

I’ll never forget the stunning essay you wrote a couple years ago but had no idea you’d gone home for treatment mid-school year in college. I’ve oscillated between both sides of the spectrum–under and over-eating, using food as a coping mechanism or a tool when I’ve either pursued an escape or needed to feel further grounded.

The irony of my tango with any of it is that I think pregnancy actually kind of healed, or put to rest, a lot of my wrestle with self-worth and the ways I am prone to use escapism (I couldn’t drink and could barely have coffee) to avoid confronting it. It sounds so expected, even eye-rolly, but the pregnancy forced me to take care of myself in a way I didn’t even realize I wasn’t taking care prior. My body would just like reject the physical sensation of feeling either too full or too hungry. Its demanding a sort of steadiness through balance in order to function at a basic contributing-human level taught me about a) how extreme I can be, b) the real definition of self-care. Not to mention, I existed for a purpose that seemed far greater than myself, although to the point about self-care comes one about self-love: There is no purpose greater than the sum of ourselves, and that–you, me, everyone–is the reason we must fight to be good to ourselves. Beginning to understand this on a cellular level was wildly freeing.

I say irony re: my tango, by the way, because I lost A TON of weight following my pregnancy. My thyroid was all over the place, breastfeeding sucked the daylights out of me, and the internet body-shamed the shit out of me when I was in the heat of that thinness. It was the first time in a long time that I actually felt super solid and steady and in love with my life and self and it sucked that an old story was being projected onto me. I never wanted to talk about it publicly because to do that seemed to validate it, but I felt somewhat violated. Like I’d lost my permission to be happy. Or something. When you are public with your life, you open yourself up to criticism and feedback and on most days, I marvel in this feedback — taking it, evaluating it, learning from it, all of that equates to growth.

There’s no but here.

So maybe the lesson of that period was to examine the cheap thrill of “bouncing back” into a body I never possessed in the first place; having all my clothes swimming around me instead of supporting me. Maybe I would have luxuriated in that body if it had not been for the criticism from commenters. I like to think I have more agency and moral conviction than allowing an anonymous opinion to upend my mode of operating, but you never know.

I’m still super thin–10 pounds heavier since thyroid stuff regulated, but still a couple pounds lighter than I used to be. Recently I resolved that I’d put effort in putting it back on. It shouldn’t take long, it’s like 4 pounds. And who knows, maybe new complexities will surface and I’ll have a whole old-but-new triptych of learning to share. This time with the wisdom of 3 decades behind me, two kids ahead of me and a body I really enjoy.

In the end, I think this is the best our gift guide could have given.

I just wish I wasn’t so damn earnest all the time.

Feature photo by Alistar Matthews, Prop Styling by Sara SchipaniArt Direction by Lorenza Centi.

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