How to Find and Put Together Cute Vacation Outfits

Updated: May 29

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If you live out in the middle of nowhere, or literally anywhere in the Midwestern United States, you might not always have access to cute vacation outfits. Even if you do have access, more options can't hurt (says me... my boyfriend and my wallet might disagree). So here's my method to the madness that is trying to be your absolute cutest, most picture-ready self while not overpacking and not looking like you're trying too hard.


It's actually pretty easy - don't worry.


Going on vacation is amazing for a million reasons, but buying new outfits is without a doubt in the top 5 - for me. The best thing about vacation outfits is that they can be completely outside of your normal style and nobody says anything. This glitch in the simulation gives you a little wiggle room to be creative without feeling so judged. There's less than a 0.01% chance you'll ever see the people you see there again, so why not wear the snakeskin mini skirt?


The first step to putting together a great vacation outfit is finding the pieces.





1) Decide on a vibe


What kind of look are you going for? Your usual? Are you changing it up? Is it warmer or colder than what you're used to? Do you need to buy a coat? Is it streetwear, boho, preppy...? If you haven't solidified the look you're going for, check out Pinterest for inspiration. Try typing in the search bar "trendy outfits for men/women" or "boho outfits women" or "streetwear outfits men" and go from there. As you respond to pins (saving, liking, commenting, etc.), Pinterest will suggest more pins that are similar. This can be a good way for you to find the style you like.


The way I dress when I'm traveling is definitely different than when I'm at home. I live in the Midwest, so I'm mostly in sweatpants and leggings or business casual for work. While I'm traveling, I love dressing up in flowery dresses and flowy, long skirts. I love wearing bright colors and patterns and feeling comfy, but cute.


If you're planning on going with your usual look, check out your favorite stores to see if they've released anything new that fits your style.


If you want to switch it up, we're going to be going through a fun lil process.





2) Find stores within your price range that sell the style you're going for


An easy way to do this is to find an influencer on Instagram with the same style. They'll usually collaborate with clothing brands to promote the products, or you can find the clothing brands commenting on their photos. This can also be a good way to find other people with that same style for more inspiration.


You can also take the "rabbithole" approach, which is where you do a Google search or Youtube search, and just keep clicking on things until somehow you got way more information than you were looking for.


**This article was written during quarantine, so I will only be recommending online stores in this article.


If you have the ability to shop local or shop small business for your vacation outfits - do it! It's not only better for the economy, but it also makes it less likely that you'll be wearing the same shirt as someone else when you get there.


For trips I have planned 4+ months in advance, I like to see what Zaful, Romwe, and other similar stores have. The clothes on these sites are insanely cheap, but they can take really long to ship and sometimes they're much smaller than you'd expect. Be wary when you shop, but I've bought a few things that turned out just fine with no problems. The reason I save places like this for trips planned far ahead of time is that I want to have time to get something else if it doesn't turn out as expected.


For trips I have coming up in a couple months, I like to shop at Quarter Moon Boutique. It's a local shop in Tallahassee, Florida, and they have the most comfortable clothes I have ever put on my body. I also like AloYoga, but my wallet does not like AloYoga (think "on sale" for $94). I like to buy on DePop, Etsy, and sometimes, when I want to torture myself, I shop at Free People. (Shopping at Free People is torture because EVERYTHING is cute and EVERYTHING is expensive, which is a problem when you can't talk yourself out of buying things.) Nordstrom, MadeWell, Tilly's and Cotton are some good options also.


For trips I have coming up in a couple weeks, I look on Amazon or Fashion Nova. Amazon is an easy place to get sarongs or basics (crop tops, tank tops, tee shirts, running shorts, etc.) And for my fellow thick-thigh ladies, Fashion Nova has great jeans. I know that ordering jeans online almost never goes well, but trust me when I say it's worth a try. If you get the stretchy denim, they feel more like leggings than jeans (jeggings) and many of the high-waisted jeans have stellar muffin-tuckers.


A muffin-tucker is a thick band on a pair of pants that comes high enough to tuck in your muffin top, without coming up so high that you have a camel toe. It's not an easy task for a pair of jeans.


Now that I've been traveling for a while, I don't need to go on full-on shopping sprees whenever I plan a trip. I can pretty much take the vacation wardrobe I've put together over the years, and buy an extra piece or two to change things up.








3) Now that you've found the stores, find the pieces


Your wardrobe should definitely have a "base" of basics. So you should have a clean, nice-looking pair of jeans, a couple solid-color shorts, a couple solid-color tees, etc.







For me, here's my list of basics I bring with:

- black tank top

- white tank top

- neutral color underwear/bras

- black sports bra

- solid-color crop top

- dark wash denim shorts

- black t-shirt


And then I go from there.


The basics will come in handy more times than not, so make sure you have your list. And feel free to add some or replace some or take some off the list. Your list of basics will depend on your style, what you wear most of the time, how you wear it, etc.


Once you've collected your basics, this is where the fun shopping comes in. Look for clothes that align with the vibe you're going for. If you need to - make a "Vision Board" board on Pinterest so you can look back to the pictures while you shop for inspiration. Try to find pieces that match, or are similar, to the ones you saved at the beginning.





4) Accessorize


The important thing to remember when it comes to accessorizing for vacation is that your suitcase has way less space than you think it does.


The trick is to pick one color for your jewelry - so wear all gold jewelry, or all silver. This will not only help you keep track of your jewelry but also you won't have as many decisions to worry about when getting ready.


You can find sets of jewelry online or you can pick up little pieces of jewelry as you travel. I personally like to find my jewelry out and about in the world. A lot of times when you find it while traveling, it'll have a story with it, which makes it mean that much more. For example, I bought a necklace in Italy that has been blessed by the Pope - how cool is that?!


When it comes to bags, keep them small. I try to bring no more than 3 purses with me for a 10 day vacation. Truthfully, you don't need that many and you can just set your purse aside for pictures (that way you don't have repeats in all of your photos). The good news is that when you're on vacation, you usually only need to fit your phone and your wallet in your purse, so you can bring smaller ones (and maybe fit an extra).


If the look you're going for involves hats, check some out. Or maybe you like the look of wearing a million rings. Or maybe you love a certain kind of sunglasses. Find little pieces that can make even your most basic pieces stand out.


And that's it. That's how you find your next vacation vibe!


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About the Author:





I'm Anna Mills - a travel agent, blogger, and author of the book "100 Ways to Make Travel More Affordable". I have been a guest on the Trip Sister's Podcast and TripScout's Roadtrip Expert Panel. You may have seen me in Texas Lifestyle Magazine, Opploans.com, or as a Rising Star for Travel Market Report.


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