Preppy Style Guide: Travel Outfits

Hello from Nantucket! I’ve actually already left Nantucket but these are the first photos I’ve shared from our trip! My friends and I had the best vacation to Nantucket… I truly can’t recommend the island enough! It’s a pretty easy two flights to Nantucket from Charleston but still a travel day. I wore the most comfortable, yet still cute, travel outfit for the journey! I wanted to share it with you so here is a little preppy style guide: travel outfits edition…

Top (more sizes here) / Jeans (also love these) / Purse / Tennis Shoes / Suitcase

Preppy Style Guide

Y’all always love my posts when I share preppy style ideas and preppy style guides. Since I haven’t shared many travel outfits, I thought I’d share a preppy inspired travel look. For a look back at some preppy style of mine in the past here are a few posts to love: preppy spring outfits, nautical stripes, exploring Carmel Valley, an affordable red + white + blue outfit, a preppy shirtdress, preppy earrings, and preppy Valentine’s Day outfits.

Preppy Travel Outfits

Feminine Sporty Travel Outfit

So, how about my preppy travel outfit? I wanted to be comfortable but also look cute because I was so excited to land on Nantucket and to meet up with my friends right away upon on our arrival. I love this airplane look so much because the tennis shoes and jeans allow me to be quick on my feet, comfortable, and sporty in every way necessary for a day of travel where breaking out into an airport sprit can happen at the drop of a hat. However, my billowy eyelet top and straw tote keep my outfit feeling feminine and fresh.

Hence, a feminine sporty travel outfit! This is my uniform for travel days with the only extra addition being a cardigan or a sweater in the colder months and a pair of trusty Ray Bans for when I step out of the airport. This outfit kind of reminds me of old street style photos I used to love so much caught of bloggers (can these come back in a big way again?) because this is something I could see on someone on the street and actually translate and wear myself!

Cozy Chic Preppy Cardigan Travel Outfit

A cozy chic travel outfit is one that is dressed up but still incredibly comfortable for a full day of planes, trains, and automobiles. Have you ever talked to your parents or grandparents about how they dressed for the airport? Being cozy was not part of the equation! However, times have changed and now being cozy is allowed. I think a pullover or a hoodie really makes a travel outfit look casual so to keep it on the chic side of cozy, I recommend wearing a cardigan. Cardigans are easy to wrap up in and stay warm in on planes but also not a sloppy layer so it’s a winning wardrobe piece!

Classic Preppy Button-Down Travel Outfit

If I’m not wearing a sporty feminine travel outfit or a cozy chic cardigan travel outfit, I’m wearing a classic preppy button-down travel outfit. Button-downs and oxford shirts are timeless and warm, which is always a bonus when traveling (planes are so cold!). No matter what, button-downs look polished so wearing one immediately helps you achieve a preppy travel look while also avoiding a sloppy travel look. I love all oxford shirt styles from oversized boyfriend styles to slim fit styles. There are so many classic American brands that make perfect button-downs and oxfords from Ralph Lauren to J.Crew and from Tommy Hilfiger to Vineyard Vines so you can’t go wrong.

Preppy Travel Style For Men

When we’re traveling, Edwin goes for a casual, put together, preppy look too! He always wear practical shoes, usually a pair of desert boots, Nikes (these are his current Nikes), or All Birds. When traveling, I always like when men embrace a polished preppy look (Edwin does!) so a button-down or a polo shirt and a pair of chinos or jeans is my preference. You can never go wrong with this look… polo shirts and such for the win!

Top (more sizes here) / Jeans (also love these) / Purse / Tennis Shoes / Suitcase

Get my Preppy Style Guide: Travel Outfits look:

Photography by Edwin Eversole