🚗 What I Wore on Our 5-Day Road Trip (With Links!)

Planning a family road trip? As a busy mom of three, I know firsthand that what you pack matters. You want to feel good, look put-together in those vacation photos, and be comfy enough to wrangle snacks from the back seat or dash across a rest stop parking lot without a wardrobe fail. 🙈

In this post, I’m breaking down the exact outfits I wore during our 5-day road trip—with links to everything on Amazon. These pieces were: ✅ Comfortable for long rides
✅ Cute enough for surprise photo ops
✅ Easy to mix, match, and rewear

Let’s hit the road… in style.

🧳 Day 1: Travel Day – Comfy, But Not Sloppy

Our Itinerary:
Left early, grabbed breakfast on the road, and stopped at two parks before arriving at our Airbnb.

What I Wore:

• Lightweight sweatshirt
  
• Drawstring joggers
  
• Slip-on sneakers
  
• Crossbody bag for phone, wipes, and snacks
  

🛒 Shop the Look:

• ANRABESS Two-Piece Lounge Set 
• Hey Dude Women’s Wendy Loafer 
• Baggallini RFID Crossbody Bag 

Mom Tip: Skip belts and stiff jeans on Day 1. You’ll thank me when the inevitable spill happens mid-snack pass.

🌄 Day 2: Nature Day – Layers + Movement Friendly

Our Itinerary:
Nature trail walk, local park picnic, and dinner in town.

What I Wore:

• Cropped workout tank
  
• High-rise leggings
  
• Utility jacket
  
• Walking shoes
  

🛒 Shop the Look:

• CRZ YOGA Butterluxe Tank Top 
• Colorfulkoala High-Waisted Leggings 
• Soulomelody Women Military Anorak Jacket

Mom Tip: Pick one jacket you can wear multiple days—it becomes your signature “travel mom” look.

🛍️ Day 3: Downtown Exploring – Easy, Breezy, and Photo-Ready

Our Itinerary:
Coffee shop breakfast, antique stores, and ice cream stops.

What I Wore:

• Midi dress with pockets (!!)
  
• Denim jacket
  
• White sneakers
  
• Straw tote
  

🛒 Shop the Look:

• ZESICA Boho Midi Dress 
• Levi’s Original Trucker Jacket 
• Adidas Cloudfoam Pure Running Shoes 

Mom Tip: A comfy dress = one piece, zero decisions. Bonus points if it twirls!

🏖️ Day 4: Splash Pad & Picnic Day

Our Itinerary:
Morning splash pad stop, afternoon outdoor games, and picnic-style dinner with friends.

What I Wore:

• Black one-piece swimsuit
  
• Flowy cover-up
  
• Slide sandals
  
• Wet bag for swimsuits
  

🛒 Shop the Look:

• Tempt Me One-Piece Swimsuit 
• Ekouaer Beach Cover-Up 
• Crocs Brooklyn Sandals 

Mom Tip: Always pack at least one swim-ready outfit even if you don’t plan a water day. Trust me.

🏞️ Day 5: Drive Home – But Make It Cute

Our Itinerary:
Packed the car, grabbed breakfast to go, detoured for a scenic overlook, and drove 5 hours back home.

What I Wore:

• Cotton tank top
  
• Paperbag shorts
  
• Lightweight cardigan
  
• Slip-on sneakers
  

🛒 Shop the Look:

• Amazon Essentials Relaxed-Fit Tank 
• GRACE KARIN Paperbag Shorts 
• Miz Mooz Leather Slip-On Sneakers 

Mom Tip: This look was my most complimented outfit. And yes, I wore it again two days later. 😂

🎒 5 Essentials I Always Pack on Road Trips

1. Wrinkle release spray – Iron who?
   
2. Packing cubes – Each kid gets one. No more suitcase chaos.
   
3. Mini laundry bag – Dirty clothes go in, stress stays out.
   
4. Extra hoodie for every child – Just trust me.
   
5. Portable first aid kit – Bandaids are the new currency.
   

🧡 Final Thoughts

Your road trip outfits don’t have to be boring or blah. With a little planning, you can build a 5-day capsule that covers every adventure—from hiking trails to late-night ice cream stops—with zero stress and a lot of style.

If this post helped you plan or inspired a look, I’d love for you to tag me on Pinterest or Instagram @RelaxationPlanner and show off your travel style!