7 Things That Are Always Chic, IMHO.

A reminder that this list is not definitive, and that you can have your own list. The limit does not exist!

The plan was great, if I do say so myself: I had a work trip this week to London, a wild 48-hours of board presentations and meetings with luxury fashion brands, meeting up with my chic colleagues, and even a scheduled moment at the pub. The outfits were planned! The bag was packed! The ensuing story—meant for today—was cute! I could see it all!

But we make plans and Mercury Retrograde laughs, and in my case, that meant a raging fever and a throat full of knives, and not leaving my house a single time since last Sunday. The closest I got to outside was opening the door for yet another Postmates delivery of an overpriced smoothie and the world’s most spendy bone broth.

The only good thing about a dreary haze of a week like mine is that it forces you to slow down, and instead of flying halfway around the world, I actually had a minute to think. And by “think” I mean “scroll TikTok,” let’s be honest. The other night whilst doing so, I came across a relatively straightforward video in which a creator was talking about things she thinks are chic. She’s young, so it was full of sweet things like having a signature drink at a bar (“a vodka soda doesn’t count,” she says) and having a closet of sundresses for hot Chicago summers. And it made me think: What do I think is chic?

Before I get into it, I want to acknowledge that what one thinks is chic will change over time, and depends on your life circumstances. If you’d asked me this when I was in high school or college, I wouldn’t have understood the question. Chic simply wasn’t on my radar; I was interested in hotness.

To be perfectly transparent, if you’d asked me this when I was in my late 20s or early 30s, I’m still not certain I’d have a great answer. At that point, I was interested in coolness. It was the heyday of the model-off-duty look (think: Alexander Wang x Erin Wasson), which was not for me per se, but I was keen to find my own version.

But now, in my genteel 40s, I’ve finally got more of a grasp on the topic, and it’s surprisingly easy to list what I think is chic. Here are a handful of my personal favorites; if you have a moment, let me know in the comments.

This girl was not interested in the concept of chic. HAHAHAHAHAHHA.

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Also: I have an upcoming interview with my luxury travel agent friend, Rebecca Bullen, who gave us all her insider travel secrets last year. I’ve already sent her a bunch of questions, but if you have anything you’re curious about (like what should you be booking now, or where the coolest new hotel is opening), just leave a comment and we’ll try to get it answered!

Photo from the Rosewood Kona Village, where Rebecca sent us last spring. 11/10 recommend her and this hotel!

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1. A perfect gray t-shirt / The Great The Boxy Crew ($95) in Heather Gray

In my entire closet, I have two perfect gray t-shirts, and I guard them with my life, because the right gray is literally the best thing in the entire world. A perfect gray t-shirt can be the biggest workhorse in your wardrobe, and truly has the ability to make anything from jeans to a giant ballgown skirt look incredible.

My original perfect t-shirt is a gray deep v-neck American Apparel t-shirt I got in the mid-to-late 00s, and it’s flawless. The other perfectly chic t-shirt that has saved my outfits more times than I can count is The Great’s The Boxy Crew ($95) In Heather Gray. I love the brand’s The Slim Tee ($95) as well, and honestly you can’t go wrong with either shirt. They’re impossibly soft, and just the most ideal shade of gray known to humankind.

If you have ever trusted me about anything, it should be on the topic of the perfect gray t-shirt. And that The Great makes the best ones. Period.

2. Bringing your own polish to the salon / Hermes Nail Enamel ($50) is always chic.

No shade to folks to like to experiment with their polish; I totally understand why you would like to pick color at the nail salon. I’m just saying, I think there’s something really chic about women who bring their own polish. It’s chic that they’re the only ones who have used it (yes, I have some germ issues). It’s chic that they know themselves so well, they’ve already figured out what they want ahead of time (I like the decisiveness). It’s giving I know who I am, and that’s fundamentally chic to me.

As for the polish itself, I own a wide range of brands and colors, but my YCOHO would be Hermes nail polish in 64 Rouge Casaque, which is currently 15% at Nordstrom right now for reasons I don’t understand. Also, I know this is an insane amount of money for polish, however, I will say that 1) The colors are superior to anything else out there 2) The polish lasts longer on my nails than any other polish I have ever used and 3) I literally buy a bottle every two years at most, and I don’t buy other polish now. I have one bottle of Rouge Casaque for summer and a bottle of 85 Rouge H for winter, and that’s that.

Once you go Hermes polish, you never go back.

3. Women in menswear / Karla Welch on the cover of The Hollywood Reporter

First of all, let’s be clear: I think Karla Welch is chic. Today, tomorrow, always. I find everything about her chic: Her politics, her cropped hair, and definitely her personal style, which always plays with traditionally masculine elements in ways I find deeply sexy and unquestionably elegant.

In the photo below, she’s wearing a Giorgio Armani shirt and tie, with vintage Levi’s and a Cartier watch, and it’s just everything. Here’s another look at a similar outfit; perfect, no? Does it make me want to buy a classic rep tie from Brooks Brothers? Not no!

More examples of Karla being chic: In a barn jacket, in nothing but a Tiffany Elsa Peretti ring, in a suit, with slicked hair, in polka dots (!!) x two (!!), in a vintage gown, in a tux…the list goes on and on.

karlawelchstylist

A post shared by @karlawelchstylist

4. A bitchy black heel / Gianvito Rossi Gianvito 70mm Suede Pump ($795)

Now here’s the thing about a bitchy black heel: There are incredible options via a wide range of brands and price points. For me, for my feet, and for my investment shopping, it’s always going to be this style from Gianvito Rossi. It’s super comfortable, gives me height while still be walkable, and makes anything I’m wearing look more expensive. That heel height might seem low to you (in that case, look at the 85mm version), or it might seem high, but that part doesn't matter; what matters is the material and the silhouette. Suede is just better than leather here, and the pointy toe and slim heel are key.

Jimmy Choo makes a great version too, and I of course love the Manolo BB pump, a true classic, which is a bit more narrow in the toe box than the Gianvito, if that matters to you. And you can’t forget Christian Louboutin’s iteration, which was named for Kate Moss, the high priestess of chic. My point is, all the greats make a version, and for me, this is a wardrobe staple that works so hard it’s worth buying the best version you can get.

5. A slightly sporty, high-neck tank top / J.Crew Perfect-Fit High-Neck Tank ($20.65 on sale)

To be clear: I am not talking about a sports garment here. No moisture-wicking material allowed! Instead, this should be a 100% cotton or lightly stretchy cotton tank top that has a high neck and preferably some sort of racerback-adjacent silhouette. There’s something so elegant about this shape; it’s not coquette-ish like a cami, not as male gaze as a trad halter, and less expected than a simple tank. I love how it nods to ‘90s minimalism too.

I adore J.Crew’s iteration, which is also bra friendly; my tip is to size down. I also recommend James Perse’s Ribbed Stretch-Supima Cotton Tank ($95) and continue to fall in love with the brand’s t-shirts over and over again. For a dressier iteration, I like Citizens of Humanity’s Akira Ribbed Knit Tank Top ($150), and for a steal try The Gap’s Modern Rib Halter Tank Top ($19); the navy with white trim version is really good too.

If this isn’t straight out of the ‘90s, I don’t know what is?

6. Monochromatic outfits.

The color of the look is variable and seasonal, but monochromatic dressing as a concept always looks chic to me, whether it’s a non-boring neutral like olive green from head to toe, or even a shocking or unexpected color, like Timmy in butter yellow at the Oscars or Selena doing an all-red look last week.

And brands are making it easier than ever to do with the rise of so many sets or coordinating pieces. Like Reformation’s Moya Linen Two Piece Set ($298) which is an a-line skirt and simple blouse that would make a statement in red. Or Aligne, which makes a pistachio duo that’s just divine, and J.Crew does it too in a heavenly red sand color. (PS: The Soleil pants are delish.)

Also: click on the @whowhatwear IG post below; the olive green slide is obvi my fave)

whowhatwear

A post shared by @whowhatwear

7. Clothes that fit.

This is both the easiest and the hardest thing to get right. Easiest because a good tailor can literally make anything fit your exact body, assuming you did my trick which is to buy a garment that accommodates the biggest part of your body with ease, and then take it in from there. Hardest because you might not want to take things to the tailor, in which case you have to try on lots of things to find something that truly works with your exact form.

And look, I get it: I used to go to the tailor on a monthly basis and it was worth all the time spent, because a few tweaks can make that vintage piece or that great basic from the high street look 1000 times better. But that’s not my life now, as someone with kids and a hectic career. Now it’s an every six months, if I’m lucky situation. So I’ve become stricter about what I buy, knowing that I’m less likely to alter it.

But there is nothing that makes someone look better than well-fitting clothes. Irrespective of your personal style, your body type, or your taste, if your clothes really fit your body, you will look chic. I stand by this wholeheartedly.

Other Assorted Things I Find Chic: Slicked back buns and cunty little bobs, cocktail shorts, healthy and clean no-polish nails, white Levi’s 501s a la Tonne Goodman, a no-bra tux look, commitment (to maximalism/minimalist, full glam/no glam, I don’t care just say it with your whole chest), patina, aviators, Cate Blanchett (in general) re-wearing red carpet looks. But that’s just me. Tell me yours!!!

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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.

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