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.

*This post contains affiliate links*

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

Planning Fall Outfits for a Vacation

fall outfitsImage 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:fall outfits

fall outfitsPhoto 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. fall outfits

fall outfitsImage 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. fall outfits

fall outfits

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?

fall outfits

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. fall outfits

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!


  1. Ooh fun shopping trip! We share most weather with London, and I’ve been wearing my trench coat with a (cotton) scarf this week because it’s quite blowy, and it’s definitely boot weather!

  2. I Love The Over-sized Sweaters. My Mom Is Taking Me For A Belated Shopping Trip Soon, so Might Have To Look For Some!

  3. It’s pretty chilly in Scotland right now! So you will be good to get some cardigans.

    I love the maxi skirt, where is that from?

    Hope you got my guest post now, I’m a bit concerned they have got lost in a spam folder somewhere. xox

  4. Edinburgh was much colder than London when we went (granted, it was November) so be sure to bundle up!

    I am dying to go Fall wardrobe shopping. I just purged my closet and it is looking sparse (it feels like I have nothing to wear). Any who, I love all these options and I am super excited for you! Plus, since you haven’t packed yet, there’s still time for me to stow-away in your luggage! 😉

  5. I hope your trip is amazing! We went to Florida this summer vacation, of course I needed tons of new clothes. That also meant I didn’t buy clothes for back to school (I work in a school) so I’m trying to make my summer vacation clothes appropriate for work. I can’t wait to buy some new stuff for fall! I’m with you on the chambray shirt. I bought one during the summer on clearance and I can’t wait to pair it with colored skinny jeans and boots or flats. Good luck shopping!

  6. Yay for Fall shopping! Chambray and a denim jacket are definitely must haves! I love my chambray shirt that I bought at Target, but I wasn’t crazy about the fit of their denim jackets. I ended up going with one from Old Navy. Happy shopping! 🙂

  7. I love it all! And I love that you get to get a jump start on your fall wardrobe. When I was in Boston last month, it was hotter than hot, but I loved doing dresses. It just seems so much more put together.

    Also – I got the CUTEST chambray top at JCPenney recently.

  8. Jess @ Little House. Big Heart.

    I love that navy dress! I’d wear it everywhere!!

    I love planning my outfits and how everything can mix and match for travel! Are you packing light?

  9. So inspiring! Now I’m ready to go shopping!

  10. Kendra Hughes

    is it possible that you have a link to where the grey boots are in the pic with the teal mint jeans and white blouse with grey sweater…i am in love with those boots!!

  11. Kendra Hughes


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