The Tip Jar #7: I’ve Got a Family Spring Break Trip to Pack For — What Am I Packing?

The only two hats you need for beach hangs, flight delays, and every vacation hair moment in between

And we’re back! Coming in HOT with another installment of The Tip Jar.

Last month, we raided the men’s section. I teed up a plethora of clean cuts, cool basics, and how to make them distinctly yours—without overhauling your closet, and most importantly, your budget.

The Tip Jar #6: How to Borrow from Menswear

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This month, I’ve got your head seasonally covered. Without further ado, let’s dive in.

A great outfit is all about the details and the right accessories can make even the simplest look feel intentional. Which brings us to this month’s reader request:

There are a bunch of great recent Substacks that have this topic covered -

Abby Arad

has your ultimate Spring Break Checklist,

ChickLits

shares her Airplane Mode and Beach Bound Roundup, and

Sogole Kane

gives you the perfect reasoning behind investing in white pants.

I thought I’d take a different approach with this request and shift the frame.

But first, a little backstory. My childhood home is a quick 1.3-mile jog to the beach. And yet, I’ve always had a complicated relationship with the sun. I’ve never truly been a beach bum, even though I married a surfer (the irony’s not lost on me). Over 20 years ago, I was diagnosed with melanoma on my left arm, and ever since, I’ve taken my sun protection very seriously. Which is why a hat is my most prized accessory.

In my opinion, there are only two hats you really need this spring and summer. They’re both incredibly chic and can be total game changers, especially on bad hair days, to pull a look together with minimal effort. Welcome the baseball cap and sun hat to the chat.

For When Time (and Dry Shampoo) Aren’t on Your Side

You’re jetlagged. You’ve overslept. You’ve got two minutes to get downstairs before the buffet ends, and there is definitely no time for a shower. It’s not revolutionary, but the baseball cap is your new best friend. Kendall Roy has been wearing his for years, and you repping your favorite team works too — but those are the obvious choices. Let’s take it a step further.

I love adding a bit of personal flair to the look—a great conversation starter if you’re a solo traveler looking to make a new friend…or spark a little vacation romance. Wild things can happen when you’re on vacation. White Lotus, anyone?

All of the caps below are the perfect addition to a casual look, but each one cranks the outfit up just enough to feel a little more thoughtful than the average cap—and a lot more you.

• Full Stop. Etsy should be your go to destination when you need a personalized cap. A colleague of mine owns this zipcode hat. A big fan of this state hat. Or pronounce your area code. All can pay homage to your current residence or your childhood hometown.

• Elevate your beach ensemble with this chic raffia cap from Hat Attack.

• This embroidered hat from Zara gives me Paris in the springtime energy.

• This hat showcases one of my favorite seasonal fabrics—eyelet. Soft, feminine, and just the right touch of sweet.

• Wayforward is a quirky West Village embroidery shop I recently discovered. They do customized embroidery too. I’ve got my sights set on a custom Beckham button-down, but if you own a wiener dog - this cap is absolutely for you.

• Favorite Daughter has you covered. Need I say more?

• Ciele Athletic makes my favorite running hats. They're colorful, unique, and offer UPF 50+ sun protection. I’m currently feasting my eyes on her.

If I haven’t convinced you yet,

Intuitive Style

delivers spot-on suggestions, Pinterest-worthy inspo, and personal closet picks in this perfectly tailored post:

Issue 63. How to style a baseball cap when your style is *not* sporty

A baseball cap is your go-to hat for a casual vacation fit, but if you are looking for something a little more elevated, then the sun hat is your best altnernative.

For When the Forecast Calls for Shine… or a Bit of Shade

Sun hats wear a lot of hats. They don’t just shield your face and shoulders from the season’s strongest rays — they can be the finishing touch that pulls your whole outfit together. They can even make such a strong statement that everything else you’re wearing becomes an afterthought.

I’ve searched and searched over the years for the perfect sun hat, but there’s always something just a little off. The fit is slightly too tight. The price feels outlandish for something you’ll only wear occasionally. The material doesn’t travel well. Or there’s one design detail that throws it off — like wearing mostly blue, but the straw hat is trimmed with a black grosgrain ribbon.

But then I discovered Lorna Murray — and all bets were off. An ethical and sustainable Australian brand where effortless glamour meets coastal bohemian, their hats somehow manage to be both functional and fashion-forward. A winning combination in my book.

[Pleated with perfection.]

There’s no other hat on the market quite like a Lorna Murray. They spark immediate joy when wearing.

Exhibit A

[Seen here trying on the Summatra Capri Hat right out of the box.]

Here are four other reasons to consider one for yourself:

• Thanks to their innovative pleated construction, these hats can be folded like origami, making them easy to pack without losing their shape. The best travel companion out there.

• The brand’s commitment to sustainability ensures minimal environmental impact while supporting traditional craftsmanship by artisans in Southeast Asia.

• Their 100% natural grass fibre material is certified UPF 50+, protecting your precious skin from all the elements.

• Their pleated construction is the delicate, feminine detail you didn’t know your wardrobe was missing. It adds a touch of elegance and sets them apart from every other sun hat out there.

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Whether you’re booking flights, lounging close to home, or just dodging a bad hair day, let your hat do all the heavy lifting this spring and summer. And remember the mantra: may your caps be personal, your sun hats packable, and your vacation snaps 10 out of 10. Same time next month?

Until then, stay shady—in the chicest way possible 😎.