3 Things You Should Read And 2 Travel Outfits I Swear By.

An excellent airport outfit reduces stress by 59%. It's science.

Hi everyone! I’m so glad you’re here. Memorial Day is almost here, and that means: Sales, sales sales! And travel, travel, travel! Next week I plan on covering some of my favorite pieces at reduced prices, but today I’m more interested in exploring what to wear whilst on the road. 

A few weeks ago I flew to New York for the premiere of City On Fire (watch it on Apple TV), which my husband worked on, as the show’s music supervisor. I will be honest; I haven’t traveled a ton over the past few years due to the whole small-kids-and-a-pandemic thing, and to say I was startled by what I saw in the airport was an understatement. So I want to talk about that, too.

Before we dive into it, I have a question for you all. Can we make this a place where we share what we’re reading and why we loved it? Yes, this is about books, which longtime readers of this newsletter know I love to chat about (and there is a roundup of my favorite recent reads coming as soon as humanly possible), but also the newsletters and articles we can’t stop thinking about?

Please?

I’m happy to kick this off, so here are a few of mine.

---

NEWSLETTERS

Line Sheet by Lauren Sherman

When I tell you there’s no one doing it like Lauren Sherman right now, I mean it. She’s the fashion industry’s best journalist (SAID IT), and her new venture with new media company Puck is legit the bee’s knees. She gets the best scoops, has flawless sources, and knows everything first and with better details. The Line Sheet is the newsletter form of sitting at the most insider-y fashion editor dinner, where everyone’s talking about the industry’s biggest and breaking stories. 

She covers a lot of ground, from the drama at LA’s beloved Horses (one of the go-to spots for fashion dinners), to what’s the deal with the CEO who ran the Something Navy clothing line (into the ground), to how Tory Burch became cool (the line, that is; the lady has always been IMHO). It’s all brilliantly contextualized, impeccably reported, and just a pleasure to read. Delicious. Just delicious.

Jane on Jeans by Jane Herman

Of all the people I have met in my life, there is no one more knowledgeable about all things denim than my friend Jane Herman. A longtime fashion industry vet (Gap, Theory) and former magazine writer/editor (we met as assistants at ELLE; she also worked at Vogue for years), she’s evolved into a founder and designer with her company The Only Jane, which makes the world’s best jumpsuits. (She also co-founded the amazing site Jean Stories, which was excellent.)

So you can only imagine how thrilled I am that she’s sharing all of these denim insights via her new newsletter, Jane on Jeans. Her first installment went live this week, and it’s just impeccable. A blend of truly aspirational, completely interesting, and warmly pragmatic (look at the comments; she’s in there advising readers on their specific denim queries!), this is a must-read for denim devotees and dabblers alike. 

STORIES

“If I Were a White Woman, Would My Child Have Been Born Two Months Early?” by Cecilia Rabess for Vogue

This brilliantly written personal essay cracked me open in so many ways. Every time I think I have some comprehension of my privilege, I’m reminded anew of how all encompassing it is. This piece is a must-read reminder of the mind-blowing inequity in this country, especially when it comes to birth. I really hope you read this story, and if you can join me in supporting the Black Mamas Matter Alliance, that would be much appreciated.

BOOKS

Just wanted to say thank you to everyone who sent me ideas for my Books of the Summer List, which I am trying to race through, albeit thoughtfully. Truthfully I will probably just do what I normally do, which is stalk Tyler McCall’s Instagram for ideas. (She single handedly is responsible for like 83% of the books I’ve purchased in the last couple of years.) And also, I regret to inform you that I do not have a Goodreads, but thank you for the inquiries. As you fall in love with new books, will you please let me know in the comments?

Most recently I really enjoyed Fake by Erica Katz, which is set in the wild world of high-end art forgery.

---

AIRPORT OUTFITS

As I mentioned earlier, on a recent LAX → JFK trip, I was gobsmacked by the absolute shitshow of what people were wearing. Does that sound judgmental? Well it should, because honestly there is no reason anyone should be wearing booty shorts or have bare feet on a plane. Not because we are policing people’s bodies, but because It’s legit not sanitary? (For the record, the person wearing the booty shorts was male and I literally saw his genitals touch the seat. And no, I am not kidding.)

I’m not suggesting you dress as formally as I once did. (My dad was a commercial airline pilot, and that meant that I, as a standby passenger representing the company, had to wear flesh-colored hosiery. Even in coach! Even in the ‘90s! Forsooth!) But I also don’t think I should be subjected to the aroma of a stranger’s feet as we hurtle across the Midwestern plains. Or ever, come to think of it. 

But Hillary, I can hear the naysayers whine, who wants to put effort into what they’re wearing on a gross airplane? I’m not suggesting you hire a stylist and get pro hair and makeup before sauntering to your gate. I’m just recommended that everyone figure out a couple of travel outfits that work. 

And the best part is, once you get it sorted, you can just use those outfits on repeat. For me, there’s a great comfort in knowing that no matter what the day brings, how stressful the trip may become or how annoying the delays, at least I’m going to feel completely comfortable and put together, so if I end up unexpectedly seated next to a colleague, industry rival, former flame, or frenemy (all of which have happened), I will feel confident. 

While my exact formula changes depending on the season and what I’m loving at any specific period in my life, a few things hold true: Lightweight layers and pieces that look polished, but are secretly really comfortable are always a good choice.

Most recently that meant: 

OUTFIT ONE

The Vibe:

Nonchalant but polished, with a slightly femme undercurrent.

The Pieces:

-A simple, stretchy, long black dress. 

Commando’s Classic Maxi Slip ($138) is my longtime love, as you probably remember. I wear a small/medium, but honestly the medium/large is fine too.

-An oversized blue and white striped shirt. 

COS’s Oversized Waisted Striped Shirt ($138) is my current go-to in a size six. It’s low stock right now, so I’d also recommend J.Crew’s Cotton Voile Shirt ($98) in Regal Stripe (Madewell makes a good one too). If your wealth isn’t stealth, Bottega’s version is also quite nice and would look lovely landing at Teterboro. Ha.

-A slouchy, soft overcoat in a warm tan or cognac or even saddle brown.

Unsurprisingly, I wore my favorite (sadly sold out) A.L.C. Wilson Coat, which I am asked about every time I put it on. The dream version is The Row’s Marlita Coat in camel, but if had the money for that, I hopefully would also have the money for private. Jokes aside, Mango has one on sale that’s a nice color at a nice price. But the best thing out there right now with this sort of vibe is Anine Bing’s Dylan Coat ($800), which is more structured, but is made out of a wool-cashmere blend that’s really incredible at that price point. Investment worthy and a future classic, for sure. 

Is it odd to have a coat whilst traveling right now? Well, here’s my thing: Weather is weird. It’s going to reach the mid-to-low 50s here in LA this week at night, plus airplanes often run cold. So pick an outerwear layer that is cozy, but still pretty lightweight, and remember it also makes a nice pillow/blanket for your travels. 

-Classic black sneakers and small socks.

Are there sneakers of the summer? Sure. Do I care? Eh. I’m personally devoted to old-school, low-top black Chucks, but you do you. Just be sure to grab a three-pack of my favorite Vans no-show socks, which still are, and always will be, the best. The point is: The sneakers should be broken in and relaxed, and yes, you must wear socks because heaven forbid you don’t have pre-check and have to remove your shoes for some inane reason. 

OUTFIT TWO

The Vibe:

A tiny bit tailored, a smidge Scandi, and effortlessly cool.

The Pieces:

-Extremely chill wide-leg linen trousers.

If you do one thing this weekend, please let it be buying Abercrombie’s Linen-Blend Tailored Trousers ($80), which are honestly one of the best things I’ve purchased this year. Normally I hate pants, and have trouble with pleat fronts, but these are so dang good. I have them in black in a medium in the regular length, and they are ridiculously comfortable. Do they have an elasticized back, which is gross? Yes. Do they bag out over the course of the day making them even more capacious? Yes. Are they still bomb? Still yes. (For the record, I hide the back by wearing them with a t-shirt tucked in the front, but still loose in the back, so you don’t see it.)

Plus! They’re machine and/or hand washable, so if you wear them on the plane and then decide you want to style them again at your destination with a skinny tank or whatever, they’re easy to clean. 

-A cool t-shirt in a matching washed-out black.

Monochromatic outfits are always excellent for travel, especially if you liven them up with thoughtful accessories. So with those black linen wide-leg trousers, I have been wearing my favorite faded black t-shirts. The best one I own is an Anine Bing Lili Tee Butterfly ($100), which I am a sucker for (as I am most of her band-inspired t-shirts) because it just gives the linen trousers some much needed fuck-off energy. Mine is a small, and I 11/10 recommend it.

Again, style it by tucking it into your front waistband slightly, and leave the back undone. Also: This is probably my favorite Anine Bing t-shirt I’ve ever owned, and I have more than I’d like to admit. Trust me and buy it.

-The same coat and shoes.

UNIFORM DRESSING, FOLKS! That’s the whole point of this. I always try to make sure my travel outfit uses some of the same key pieces, like the coat, shoes, and accessories, so that I’m not packing unnecessary options. 

Okay so those are my go-to airport outfits right now. Can you please share what yours are? And have they changed? Mine used to be: An army green field jacket (pockets FTW), a slouchy horizontal stripe black and white t-shirt or a dark gray plaid button-down, stretchy black skinny jeans, and beat up moto boots. Or I’d wear a The Great t-shirt dress, the best matte opaque tights from Commando (they never itch or pinch), and the perfect camo army jacket from J.Crew. Oh, and always Ray-Ban Oversized Wayfarer Sunglasses ($163)  in black, which have been my primary sunglasses for the better part of a decade. 

---

Okay friends, that’s it for now. If you want to follow me on @hillarykerr, I’d love it. And if you have anything to say or ask (preferably nothing terribly mean), please drop me a note either via DM or in the comments below.

As always, thank you for taking the time to read this post. I’m truly so glad you’re here. If you like what you’re reading, please consider sharing this newsletter. All products mentioned are independently chosen, and some may be affiliate links. Your support is appreciated.