The Packing Tips I Live By (For All the Seasons of Travel)

Packing for a trip can feel overwhelming, but with a few simple strategies, you can travel light, stay stylish, and be prepared for any weather. Whether you’re heading to a winter wonderland or chasing the sun, these packing tips will help you maximize space and minimize stress.

Packing Tips for Every Trip

1. Get Your Roll On
Rolling softer items like sweaters and tops helps prevent wrinkles and saves valuable suitcase space.

2. Stuffing for the Win
Tuck scarves and socks inside boots to help maintain their shape and make the most of your luggage space.

3. Coloring Coordination
Choose pieces in coordinating colors so everything mixes and matches effortlessly.

4. Accessorizing is Key
Pack items that can be dressed up or down with accessories—like scarves, statement jewelry, or belts—to get the most mileage out of your outfits.

5. Layers, Layers, Layers
Focusing on pieces that can be layered allows you to adjust for different temperatures and unexpected weather changes.

For the Winter Travelers…

Core Pieces:

  • A high-quality wool or cashmere sweater in a neutral shade (gray, black, or navy)

  • Two lightweight merino wool base layer tops (one black, one white)

  • One pair of dark, well-fitting jeans

  • One pair of wool or fleece-lined leggings

  • One versatile midi skirt that can be dressed up or down

Outerwear:

  • A packable down jacket that works for both casual and dressier occasions

  • A lightweight cardigan or shacket for indoor layering

Accessories (Minimal Space, Maximum Impact):

  • Two winter scarves—one neutral, one with a pop of color

  • A warm beanie or hat

  • One pair of gloves

  • Two pairs of warm socks

Footwear (Wear the Bulkiest Pair While Traveling!):

  • Waterproof ankle boots that can handle winter weather

  • A pair of comfortable walking shoes or sneakers

For When You’re Heading to Warmer Temperatures…

Core Pieces:

  • Two lightweight cotton or linen t-shirts

  • One sleeveless blouse that can be dressed up or down

  • One or two sundresses that work for both day and evening

  • One pair of denim shorts or a neutral skirt

  • One pair of breathable, ankle-length pants

  • One light cardigan or wrap for air-conditioned spaces

Swimwear & Activewear:

  • A versatile swimsuit that doubles as a bodysuit

  • A light cover-up that can work as a casual dress

  • One pair of quick-dry athletic shorts

Accessories:

  • A wide-brimmed sun hat or ball cap

  • A light scarf that serves multiple purposes (head covering, sarong, wrap)

  • A statement necklace

  • A versatile belt

  • SUNSCREEN!

Footwear:

  • Comfortable walking sandals

  • Dressier sandals for day or night

  • Sneakers for activities

No matter where you’re headed, these packing tips will keep you stylish, comfortable, and prepared for any adventure. If you want a customized packing plan based on your wardrobe, travel itinerary, and style preferences, I’m here to help! My personalized styling service ensures that every look is tailored to you—and conveniently accessible in your custom app. Let’s make packing a breeze!

Annie Peck