Your Spring Break Alter Ego, Styled
Nailing the art of vacation dressing (and fitting it in a carry-on)
Hark! Spring break season is upon us. And it is such a mood. That glorious week of reality suspension when we assume our vacation alter egos, day drink with zero judgement and continue breaking up sibling squabbles, but in a different city. Praise.
Maybe the big city lights are calling and you’re answering texting back a week later. For some, ski runs inside a storybook snow globe town is the ideal. For others, it’s saltwater, SPF and a beach bag that will be mysteriously depositing sand in your home for the next three to five years.
‘Spring break style’ is not a single formula — Miami maximalism, Lake Louise layering, Vegas va-va-voom, Cabo casual (elevated, of course).
Trips are not one-size-fits-all, so neither is your packing list.
Which is why I built nine. Nine destinations. Nine moods. Nine outfits that make sense for wherever you’re going — practically, aesthetically, and not to be dramatic, but spiritually.
You deserve this, babe.
How to Look Like You Belong Anywhere
Embrace the culture.
Whether that’s cowboy culture, Vegas glitz or the color-drenched capital of Mexico — the through line is this: dress with the city, not against it.
AUSTIN
Alter Ego: The Cool Charismatic
This isn’t cowgirl — this is cool girl. Lean into sophisticated textures: fringe, cowhide and whipstitch elements bring depth and heart. Vintage pieces shine here. Boots > sandals, even in the spring. Austin style is an unfussy, confident wink at cowboy culture. Curated, never costume-y. Tell the bats I said hi.
HERO PIECE: A great pair of boots (suede, pony hair or cowboy) will take you far.
PACK LIKE A PRO: Layers matter – morning and night temps in March swing wildly. Throw in a denim jacket and a pair of tights for under your mini skirt.
Shop the full Austin look — plus denim tops, suede jackets and fringed pieces here!
LAS VEGAS
Alter Ego: The Desert Dramatic
I’m not a gambler, but betting on the chaotic cutout, body-con dress aesthetic feels like Russian roulette. Leave that for the bachelorette trippers. We’re turning up the style heat in a grown-up way. Metallics and sparkles? Absolutely, it’s Vegas. But measured. Elevated. Sophisticated. Chartreuse and burgundy feel unexpectedly luxurious with just enough drama, while structured silhouettes (even by the pool) ground the looks. Desert glam, done right.
HERO PIECE: Your poolside bag won’t have to battle ocean waves and beach sand, so don’t be afraid to elevate the material. Better yet, double it as your plane tote and get more wear out of it.
PACK LIKE A PRO: Vegas is the ideal spot to bring multiple personality-heavy evening bags. Nest them inside each other to save space in your suitcase. Bonus points if you can fit a pair of flip-flops in your clutch for the walk back to the hotel.
Shop the full Vegas look — plus sophisticated evening and pool pieces here!
MEXICO CITY
Alter Ego: The Elevated Explorer
I’m certain interior designers coined the term ‘color-drenching’ after visiting Mexico City. Art, culture, vibrancy everywhere (not to mention, culinary goals). Whether you’re museum-hopping or dining at Michelin-starred restaurants, embracing high-frequency color is the key.
HERO PIECE: (Okay, two pieces). First: the striped mini dress. Evening appropriate, sure — but pop it over a swimsuit for even more mileage.
Second: the fringed swimsuit and pareo combo. If it were me? I’d double the swimsuit as a bodysuit with loose, light-wash jeans and sandals for a café lunch. For dinner, I’d fashion-tape the pareo down the side and wear it as a skirt, paired with an elevated white tee, bold necklace and strappy heels.
PACK LIKE A PRO: Similarly to Vegas, you don’t have to contend with beach conditions to be by the water — your sandal doesn’t need to be a plastic flip flop. Try leather or beaded. It can easily be the only sandal you pack, re-worn throughout the trip.
Shop the full Mexico City look — plus artisan jewelry and bags here!
Doubling Down on Winter
Cold weather doesn’t have to mean boring clothes (proof: my last Substack post). Winter wonderlands await — bursting with premier shopping, fireside relaxation and snowy outdoor activities.
CHICAGO
Alter Ego: The Metropolitan Minimalist
If the wind comes sweeping down the plains in Oklahoma, it comes barreling between the high-rise buildings in Chicago. When my friends and I visited the Windy City for a college spring break, we wore the official 2008 sorority winter uniform: black North Faces, dark skinny jeans and Uggs. Bless our hearts and digital cameras. Our collective style has grown up a bit. You can’t spell Chicago without chic.
HERO PIECE: A really, really good pair of jeans that takes you from Magnificent Mile shopping to dinner at Atelier or Petit Edith. Stretch or rigid — you pick.
PACK LIKE A PRO: Sometimes the coat is the outfit. Be sure to pack pieces that bring interest in other ways — sculptural earrings, patterned scarves, chunky bracelets layered over unique colored gloves.
Shop the full Chicago look — and more denim, shearling coats and warm footwear here!
PARK CITY
Alter Ego: The Luxurious Lounger
Park City is the Aspen of Utah — ski amenities aplenty. But in case no one told you, you are not contractually obligated to launch yourself down a mountain. That’s what the Winter Olympics are for. Zero shame in the lounge game. Order the spiked hot chocolate. Attend après ski whether or not you did any actual skiing. I’m dressing for the fireside patio seating, not the lift line.
HERO PIECE: The sweater is the easiest, most versatile base no matter what you’re doing (or not doing). Don’t be afraid to splurge on a high-quality, flattering knit — you’ll wear it endlessly back home.
PACK LIKE A PRO: If you’re planning to hit the slopes, use vacuum bags for down coats and ski pants to reduce volume.
Shop the full Park City look — plus chic, snow-friendly boots, jackets and sweaters here!
LAKE LOUISE
Alter Ego: The Soft Sophisticate
Alberta’s Lake Louise feels like a glowy, romantic, cinematic escape. Monochromatic base layers allow cozy sweaters and diamond jewelry to shine. Bringing your own fluffy slippers for spa treatments feels incredibly luxe. Cream, camel and pastel-colored coats photograph beautifully against the snow. Hot springs, relaxed dining and scenic sleigh rides provide the perfect backdrop for chic winter statement pieces.
HERO PIECES: Cold-weather accessories act like jewelry, so choose ones with personality — metallic elements, colored cashmere or shearling details all work. Don’t forget sunglasses for the snow glare.
PACK LIKE A PRO: Wear your bulkiest wool coat on the plane to save precious suitcase space.
Shop the full Lake Louise look — plus faux fur coats, gloves and elevated loungewear here!
Beachy Keen
These sunny destinations each have their own rhythm — vacation looks built around the climate, the culture, and the kind of big-trip energy you want to bring.
CABO SAN LUCAS
Alter Ego: The Curated Casualist
Refined. Understated. Considered. Curated. That’s Cabo style. Pattern and color should feel like an intriguing whisper, not a shout. Resort tailoring is relaxed and timeless for a reason — maximum comfort, minimal brain power. An oversized hat. Special jewelry. One great woven bag that carries you and your lip gloss hoard through the trip.
HERO PIECE: An astoundingly versatile fringed satin dress that moves effortlessly from the beach club to the pool bar to dinner. This is the kind of piece you build the suitcase around.
PACK LIKE A PRO: Start with a base of creams and browns, then add two brighter color punches for interest (electric orange and minty blue are doing the work here). Keep it cohesive. Keep it easy.
Shop the full Cabo look — plus more resort-worthy jewelry and swimwear here!
MIAMI
Alter Ego: The Master Maximalist
When we went to South Beach a few years ago, I decided I wanted to look like a walking Art Basel exhibit. I highly suggest you adopt the same mindset. Miami rewards the bold. If you’re allergic to attention, hear me out: wearing neutrals here will make you stand out more than the loudest color combination you can conceive. Top Miami memories — lowkey stalking Vince Vaughn in a tiger striped swim-cover-up-turned-dinner-dress and dining at the Versace mansion (obviously, in Versace). I would make another trip back just to sit by Gianni’s iconic pool again — and step into the visually stunning world that is the Cult Gaia flagship store.
HERO PIECE: Something striped, something sheer, something patterned, something animal print (preferably all worn together). Sorry, couldn’t narrow it down. This is maximalism, after all. Oh, and statement sunglasses are mandatory.
PACK LIKE A PRO: Invest in a good jewelry organizer when your destination calls for multiple statement pieces. I’ve found that a sunglasses organizer also works beautifully for oversized jewelry.
Shop the full Miami look — and more bold evening and beachwear options here!
HAWAII
Alter Ego: The Relaxed Romantic
Simple but soulful, sun-soaked silhouettes and soft color palettes. That’s the island mood. Nothing fussy, forced or overstyled. Just pieces that move with the breeze and make getting dressed feel almost ceremonial. Breathable fabrics, easy layers, and swimwear that doubles as daywear — because in Hawaii, you’re rarely far from the water. Let the landscape do the talking. Here, your wardrobe is the exhale.
HERO PIECE: High-quality swimwear. For years, I thought it was better to have more swimsuits at lower price points. But I found myself reaching for the better-quality, better-constructed pieces every time — the kind with thoughtfully designed structure and special details, made from fabrics that don’t pill or fade.
PACK LIKE A PRO: Wear your sturdiest sandals on the plane. Bring a full beach look in your carry-on. Island energy starts immediately. A lightweight button-down (or three) is the most versatile piece you’ll pack.
Shop the full Hawaii look — plus elevated accessories, swimwear and warm-weather separates here!
The Passport to Smart Packing
Decision fatigue is real. I want to use precisely zero brain cells while I’m on vacation. Here is how I prep my outfits so my brain can go fully Do Not Disturb.
I try everything on ahead of time (yes — even the jewelry and sunglasses)
I eliminate anything that doesn’t feel 10/10 or has no re-wear potential
I photograph each final look (on my body or laid out flat)
I use the iPhone lift-and-paste trick to transfer the images into my Notes app.
I label each look by occasion (ex: Night #2 Dinner, Beach Look, Travel Day, etc.)
HOW TO TURN OUTFIT PICS INTO A SIMPLE LOOKBOOK:
— Press and hold your finger on the outfit image until it “lifts”
— Tap Copy
— Open your Notes app and start a new note
— Tap anywhere and select Paste
— Resize as needed
— Repeat until all outfits are together in one scrollable lookbook
— Label each look
That’s it. Your entire trip — visually mapped out.
If You’d Rather Chew Off Your Own Arm
Some people reach euphoria during the outfit planning process.
And some people would absolutely rather have a root canal.
If you wish you could skip straight to the good part — all the benefits of being prepared without any of the mental gymnastics— that’s exactly why people hire me.
This year alone, I’ve helped clients:
Build full vacation wardrobes using a thoughtful mix of existing pieces and strategic new additions
Edit and streamline overpacked suitcases
Recommend luggage and organizational tools that actually make sense
Create personalized digital lookbooks so getting dressed on the trip feels effortless
One recent client was headed to a tropical destination for a full week of wedding festivities. We mapped every event, every outfit, every accessory — and she never once had to ask, “Wait, what am I wearing tonight?”
Carefree. Confident. Clear. That’s the sweet spot.
If that sounds like something you’d love support with, reach out to me for a menu of my vacation styling packages.
Bon voyage
Alter ego jokes aside, spring break style isn’t about buying a whole new personality — it’s about dialing up a version of yourself that makes sense for the setting. Wherever you’re going — snow, sand, or somewhere in between — dress like you meant to be there. Your clothing should transport you into whatever version of escape you’re chasing. If you take one thing away from this post, let it be this:
The more thought you put in beforehand, the less mental work you have to do on vacation.
Start planning now. Your vacay self will thank you later.
Get dressed like you’re already there,
Joey
Need a personalized, one-on-one styling approach? Reach out for a menu of my styling services and packages: jordangraystyling@gmail.com
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