How a Chronic Over-Packer Can “Carry-On”

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I’m hopping a flight for a girls’ weekend and want to live the “carry-on” life!

Carry-On Personal Item Backpack

If you’re naturally a light packer, this may sound simple. As a fashion stylist and a mom, minimalism isn’t my thing. It’s my job to be prepared for every activity, temperature shift, social scenario, and just-in-case moment—with backups. Add tech devices, chargers, meds, and my deep fear of fitting all liquids into one tiny zip bag, and you can see why this keeps me up at night.

But the opportunity to travel solo, with the promise of breezing through security and skipping baggage claim, was enough to make it happen without looking like Joey from Friends wearing all his clothes at once!

1. Choose the Right Carry-On Bags

The secret is maximizing what airlines already allow. Most flights allow one personal item (under the seat) and one carry-on (in the overhead bin). Always check your airline’s size rules first, as they vary.

My personal bag
Allowed size: 18 x 14 x 8 inches
I found a backpack designed to fit exactly under the seat. It’s basically a structured rectangle, which means zero wasted space. Bonus: built-in compartments that keep everything organized. I wish I had found this miracle bag sooner!

My carry-on roller
Allowed size: 22 x 14 x 9 inches
My roller bag fits these dimensions perfectly, which is great. Disclaimer: There is an option to expand if I find some must-have souvenirs to take home. I’m only human!

2. Check the Weather

Warm trips are always easier to pack for, but this one is a mix. Daytime temps in the 50s, nighttime lows in the 30s—right when I plan to wear my cutest party tops. Translation: pack layers for versatility!

3. Map Out the Activities

There’s talk of hiking…which for me could translate to shopping. Add in nice dinners, nightlife, and dancing, and suddenly the outfits are adding up.

4. Pick a Color Scheme

This is where carry-on magic happens. I’m building a mini capsule wardrobe with black as the base color. Everything mixes, matches, and works overtime.

5. Plan Outfits by Day

Instead of packing “options,” I plan actual outfits for each day and night. This alleviates stress and unworn items.

6. Travel Storage Cubes Are a Packers’ Delight!

They save space, keep outfits together, and make unpacking way less chaotic. Once you use them, there’s no going back.

Cubes Rolled Pants Socks in shoes
Space Savers: fold pants in half, roll, pack in cubes; store socks in your shoes

Bonus win: Our rental has a washer and dryer so that I can wash and re-wear. Huge.

What I Packed

Friday
Travel: black washed sweats, black sneakers, black jacket, black/tan wool wrap scarf (perfect for layering!)
Evening: black stretch cords, black asymmetrical off-the-shoulder sweater, black boots
Bed: pajamas, slippers

Saturday
Day: leggings, sweatshirt (worn the day before), lightweight nylon (waterproof) jacket, sneakers
Evening: jeans, black sparkly tank with attached wrap cardigan, black jacket, boots
Bed: pajamas, slippers

Sunday
Day: jeans, t-shirt, black cardigan, sneakers
Evening: black jeans, black button-down, black jacket, black boots
Bed: pajamas, slippers

Monday
Travel: black washed sweats, black sneakers, black jacket, black/tan wool wrap scarf

The Essentials

  • ID and wallet
  • Toiletries and cosmetics
  • Tech and chargers
  • Hair dryer and diffuser
  • Underwear (4)
  • Bras (2)
  • Hosiery (6)
  • Day to evening bag
  • Black belt
  • Tank top for layering
  • Thin cashmere base layer top for warmth (can be worn alone)
Carry On Roller Bag and Personal Item Backpack
Carry On Roller Bag and Personal Item Backpack

And that’s how a chronic over-packer officially gets it Done! Done! Done! (Sorry, I hope my fellow moms can forgive that one!)

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anne
Anne is a career fashion stylist - her dream job. She has made getting dressed easy and enjoyable for busy moms everywhere. A natural-born shopper, she is always on the lookout for super sales, thrifted treasures, and the ever-elusive stylish and comfortable shoe! A true New Yorker, Anne did not drive or have her own washer and dryer until she moved to the burbs. Anne and her husband, Rob, are happily raising their two children, Jude and Vivienne, who are seven and a half years apart, in the aptly named “friendly village” of Mamaroneck. Anne is thrilled to connect with her fellow moms as a contributor to Westchester County Mom. Find out about her styling services at www.positivelystyling.com and follow her on IG @positivelystyling.