Planning Fall Outfits for a Vacation

Though it’s early in September and the temperature has barely started to drop, I’ve been planning fall outfits for our upcoming vacation. We will be spending two weeks traveling in Europe. We’re starting in Scotland, traveling through the English countryside, spending a few days in London and ending the trip in Paris. The forecasts there look like we will be experiencing temperatures in the 50’s and 60’s, plus plenty of rain. Fall outfits that are suitable for spending hours walking through cities and museums, enjoying nice lunches and are, of course, adorable are a must!

I have a few favorite fall outfits that I’ve pinned on Pinterest and I’m using them as inspiration for my vacation wardrobe shopping. I will probably do most of my shopping at TJ Maxx, so it’s always easier to shop there when I have an idea of what I’m looking for.

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*Originally published September 13th, 2013. Updated February, 24, 2021*

Planning Fall Outfits for a Vacation

Image via Carah Amelie

This is one of my favorite fall outfits. I love the brown boots and leggings with the cute printed mini skirt. My boots are some of my most favorite shoes, and I’ve worn them on plenty vacations, so I’ll definitely be taking them with me on our trip. Plus, I can change my shoes at the end of the day and be ready for a nice dinner.  With this inspiration photo in mind, here’s one of the fall outfits that I created for our vacation:

Photo via In My Closet

My current favorite items of clothing that I own are my maxi skirts and dresses. They are so comfortable and they look great. I wear them all summer with sandals, but could easily pair them with flats, boots or sneakers to create a fall outfit. I will definitely need a denim jacket or cardigan as well since the weather will be on the chillier side. I actually didn’t own a denim jacket before preparing for this trip. They are definitely a wardrobe staple and a MUST! With this inspiration photo in mind, this is another of the fall outfits I created for our trip. 

Image via SSense (Formerly on Polyvore)

One of my staple fall outfits for this trip will most likely consist of  skinny jeans, a t-shirt, and a cardigan. This is actually my favorite combination because it’s simple, but depending on the pieces that are paired together it can easily be dressed up or down. This look can be paired with sneakers or boots for the days when there is a lot of walking. Or you can swap the cardigan for a blazer and add a pair of heels for a nicer outfit for the evenings. With this inspiration photo in mind, these are another two of the fall outfits I created for our trip. 

I feel like the streets of Paris also call for some simple pieces, like this black pencil skirt from Old Navy. From what we’ve read online the best way to look like you belong in Paris is to wear neutrals and dress more business casual, so when in Rome Paris, right?

Photo via SSense (formerly of Polyvore)

A button down dress is perfect for strolling the cities too! On a warmer day I can just where the dress and if it’s cooler out I can pair it with leggings and a sweater. When I was shopping for this trip I did not find a button down dress, but I did purchase a t-shirt dress. T-shirt dresses are great because they can be dressed up or down, but are always comfortable. 

And of course no vacation with my husband is complete without a few romantic nights out, which means I’m definitely going to need a little black dress, like this one from Old Navy. And maybe a new pair of pumps… 😉

I built a new vacation wardrobe full of fall outfits by seeking out inspiration from Pinterest. I created looks similar to those online for a fraction of the cost and that suited my personal style and travel needs!