Fall happens to be one of my favorite times of year to plan trips and vacations. Coincidentally, also one of my favorite seasons to dress for. (So, hello chic travel outfits!)
You have the hustle of summer vacation behind you, you’ve got more time to spare, not to mention–the weather is cooler in warmer climates and much better for walking around and exploring all day! (But don’t worry, if you’re heading somewhere with warm weather, I’ve got you covered too–I cover all seasons and weather in this post!)
Maybe you’re prepping for a European adventure and need some inspo for the long flight ahead of you. (Also, you must read my Europe packing list!) Perhaps you’re headed to Cabo and need to know how to look stylish on vacation without sweating through everything you packed.
Maybe you’re planning a business trip and you need some casual but polished outfit ideas you can mix and match? (A work capsule wardrobe of sorts?)
Hopefully you’ll come away with a few ideas you can incorporate into your own personal style, no matter what your trip calls for.
Keep reading for my best tips for putting together chic travel outfits, my recommendations for the best travel clothes, plus over 25 options of cute travel outfits to copy! (Make sure to bookmark this page for your next trip!)
First, let’s get into my tips!
How to look stylish on vacation:
My 7 tips for putting together chic travel outfits in 2023-2024
#1: For the most chic travel outfits, plan outfits around your shoes
The easiest place to start when you’re building stylish outfits for a vacation or a trip is shoes. This is true especially in winter, when you’re packing and coordinating heavy shoes like boots, which IMO also happen to be the hardest kinds of shoes to style because you tend to need different pants for different boots and vice versa. This is easier in the summer months because you can easily pack 4-5 pairs of sandals or ballet flats and take up little to no room in a suitcase. The overarching rule of thumb here is that neutral colors are your friend, as it’s easier to mix and match to create the perfect outfit with very little fuss.
Here’s how I’d typically approach packing shoes by season…
One pair of cute white sneakers or even slip-on sneakers (worn on plane–maximum comfort is key here), 1-2 pair of flat sandals (usually in a nude color, secondary color would likely be black, depending on what other clothes I’m packing), maybe one pair of ballet flats, which are a great option if you’re packing for moderate temps and an occasion where you want to look polished, but don’t want to wear heels.
One pair of cute white sneakers (worn on plane), one pair flat or low-heel booties, one pair of ballet flats, one pair of loafers
One pair cute white sneakers, two pairs booties (neutral and black)–at least one of these pairs should be water resistant or waterproof. One pair of flats or loafers.
Winter: (Assuming very cold weather/snow/slush/rain)
Two pairs booties–at least one of these pairs should be water resistant or waterproof. I typically pack the least amount of shoes in winter as they take up the most room AND I also have to account for super bulky layers in a suitcase–I don’t have space for multiple shoes AND multiple sweaters, jackets, etc.
#2: One piece outfits are your best friend (dresses, jumpsuits)
I LOVE one-piece outfits, and I think this applies particularly in the summer months, when all you really need to create a great outfit is a dress or a jumpsuit. Summer months are PRIME for this–if I’m heading to a tropical vacation, I am packing mostly dresses made of breathable fabrics and maybe a jumpsuit or two! Since you aren’t “mixing and matching” anything (because, it’s one piece) go wild–prints (florals! stripes!) fun cut-outs–whatever!
The only rule for these items is that they MUST be able to be dressed up and down, and worn with multiple types of shoes and accessories. (In my case, this usually means something can be worn with sneakers for a casual look to walk around in all day with a pair of small subtle hoops and maybe a scarf, and then swapped for a dressier shoe–a pair of sandals for example–and a pair of statement earrings, for going out to dinner/drinks.)
I think this is harder to do in cold weather, but it can absolutely still be done! For example, I wore an olive utility jumpsuit multiple times for different occasions last year in Ireland where it was wet and chilly. It looked cute with both a denim jacket and a leather jacket layered over the top. A “one and done” outfit makes packing considerably easier, and also allows you to pack a lot less stuff!
Sweater: similar here // Pants: Everlane straight leg crop pants in Sandstone (TTS), similar here // Jacket: ABLE Maha leather jacket (I sized up so it’s roomier but it’s TTS.), similar here // Scarf: Old, similar here // Sunglasses: Ray ban // Headband: similar here
#3: Consider a color scheme and lean into neutral colors
Now, this only applies to things that need to be mixed and matched. I don’t count “one piece outfits” as needing to be part of a color scheme, because if you’re packing only neutral accessories and you have a one-piece outfit, it doesn’t really matter what color it is, you know? But if you’re packing mostly tops and bottoms, it will be much easier to put stylish outfits together if you have a color scheme in mind when packing!
Now, this doesn’t necessarily HAVE to mean you should only pack neutral colors, but I find that it’s often easier to gravitate toward neutrals for my main pieces and incorporate pops of color with accessories, lipstick, and shoes. I’m always itching for more color in the spring and summer, whereas for fall and winter, I usually feel most chic and put together in minimalist color schemes, like creams, camels and black, and using patterns and accessories to make my outfits most visually interesting!
Want to strike a balance somewhere in the middle? Consider neutrals along with a more muted version of a color–for example, a mustard, deep burgundy, or burnt orange for fall, which pairs easily with blacks and browns, or a muted dusty pink for dusty blue for spring, which pairs easily with the same neutrals–white, black, brown.
J.Crew turtleneck (old): similar here // Skirt: similar here // Zara coat: similar here // Everlane Day Boots (their city boots are also very similar with amazing reviews.) They make AMAZINGLY comfortable shoes!
#4: Lean into prints (especially stripes!)
I have never met a stripe I didn’t love, and it’s rare that I take a trip or vacation without at least a couple of striped items in my suitcase. (This is especially true in the fall and winter months, when I’m dressing in layers!) Why? Because stripes just make everything look a little more pulled together, visually interesting, and stylish! They’re not trendy, so they’re always in style, and they look a lot more intentional than just a plain old t-shirt.
A pattern of any kind is a great way to make any outfit more fashionable, so after considering your color scheme, start thinking of options that fit within that color scheme that also have a bit of pattern! The easiest way I find to accomplish this is with t-shirts, sweaters, and scarves.
What about mixing prints? I give that a hard YES. Just make sure when you’re mixing prints to vary the scale and choose coordinating/complimentary colors. One print should be larger and bolder and one print should be smaller and more subtle. (You can see examples above where I’m wearing patterned hair scarves with my striped tops!) Even a floral print can be a surprisingly versatile option!
I’m guessing you’ve gathered by now that I wear a LOT of scarves on vacation. In fact, it’s my #1 style hack. If you take nothing away from this post, I hope this is what you remember! Truly, the easiest way to spice up any outfit–day or night–is with a scarf. Tie one in your hair to keep it out of your face on a hot day, disguise unwashed hair (bc who has time to wash and style on vacation?!) or just as a way to make your outfit more interesting. For cooler weather, I love a cute bandana or neck scarf!
ABLE Leather jacket (c/o–reviewed here) // Similar Black Tee // A.Golde Riley jeans (took my normal size, they feel small but will stretch out, but size up if you want them roomier) ABLE Karla belt bag–use code JESSKEYS15 for 15% off! (c/o) Also reviewed it here!
#6: When in doubt, a great lipstick makes everything stylish:
Exhibit A: Candid photo taken in Dublin where I hadn’t washed my (air dried) hair in a couple of days, and I’m wearing a very simple outfit of a black tee, black Moto jacket, and jeans–yet somehow, the red lipstick makes it all look intentional. 😂 I swear lipstick can take the most boring, even disheveled comfortable travel look and make it “perfectly undone.” Some of my favorite lipsticks are Ilia (they have amazing shades but if you want something a little more subtle–Cinnabar is an amazing brick red!) and Merit’s lipsticks that make your lips pop without being too much to wear during the day!
#7: Don’t forget about coordinating outer layers + accessories!
Just like you want to ensure all your tops and bottoms can be mixed and matched, ensure that your outer layers can also be worn with everything you’re packing!
This doesn’t mean you can’t wear a statement color–for example, the coat I wore in Lisbon my first time visiting was a mustardy yellow camel color–it added so much punch to my outfits (and photos!) but still coordinated with everything else I had in my suitcase.
Same with my favorite dusty blue coat–it’s neutral enough to where it doesn’t clash with anything, and it adds a lot of personality (and of course, extra warmth) to all my outfits! If you want to bring a bright red crossbody purse–go for it, as long as you can wear it with everything else in your wardrobe!
Like I said, accessories are the easiest ways to add color into your outfits.
More stylish vacation outfits:
Striped tee & head scarf:
Stripes are always a good idea when it comes to chic travel outfits! Here I paired them with a white mini skirt (could also do shorts, white shorts or denim!) and of course, the hair scarf. Never not wearing a hair scarf on a Europe trip (especially when it’s hot!)
Bright and colorful romper:
On my recent Napa trip I brought almost exclusively one-piece outfits. (Dresses and rompers!) I loved this one that I rented from Rent the Runway–I loved it so much I bought it! I barely needed any accessories–the colorful pattern did the talking! Renting is always a great option to ensure you are well-stocked with chic travel outfits without risk of breaking the bank!
A swing dress in breathable fabrics and red ballet flats:
An easy way to incorporate color into your travel wardrobe is with your accessories–including shoes! I love a little red ballet flat. Surprisingly, red goes with a lot of other colors–it’s easy to pair with other things in your wardrobe. You can read my Rothys review here!
The Nap Dress: one of the most versatile pieces you’ll pack for warm weather
Hill House Ellie Nap Dress (this color/pattern is a few years old but they have so many cute colorways!)
The Hill House nap dress: my summer wardrobe work horse. I own it in 3 colors. I wore it day and night in August in Lisbon where it was sweltering! Their summery dresses are made of lightweight fabrics, and in my opinion, a great piece to always have in your suitcase for warm climates.
The perfect versatile blouse for a classic look:
Chic casual basics in Napa (from my first trip in February a couple years ago!) This top has become one of my bestsellers for good reason–it just goes with everything! Here I’m styling it with jeans but would also look cute with wide-leg pants, trousers, and I’ve worn it in the summer with shorts!
Exact same outfit, just with sneakers this time, (and sans hair scarf) in Dublin!
A versatile cardigan:
Very similar outfit for cooler weather–a cream cardigan instead of a blouse, and wearing that same scarf from my Napa outfit, this time around my neck instead of in my hair!
Neutrals and stripes for extra polish: (perfect for a business trip!)
VERY old photo, but would still wear it all today! Mixing neutrals + stripes is always a very foolproof combo!
Black on black: always a winning combo
Dinner in Lisbon: One of my favorite fall outfits–a black turtleneck, jeans, black boots, and a hair scarf!
the Sezane Gaspard cardigan:
Okay, you get it, right? Neck scarves are cute. 😂 Another tip: I love bringing a cardigan along in my suitcase because it’s both a first layer (buttoned up the front) and a second layer (unbuttoned, over a tee or blouse!) The Sezane Gaspard cardigan that I’m wearing here is major mainstay in my fall/winter wardrobe and I own it in two colors!
A statement coat:
Mango coat (sold out but reviewed here!), similar here // Sezane sweatshirt (I’d size up, I went with M), similar here // Sezane jeans (see outfit #1 for details) // New Balance sneakers (TTS) // J.Crew turtleneck (TTS) // similar headband
Here’s another example of a neutral but statement coat. I love this coat (got it from Mango last year) and it goes with so many things. I call this a “dusty seafoam” color and I think it makes the most basic outfits so cute. Also, another scarf, but a winter version. (Also Sezane! Don’t sleep on their accessories!)
Warm and cozy layers:
From my trip to Quebec City with Neal a few years back. Dressing for the coldest weather (we’re talking negative wind chill!) can be the most challenging of all, but I have one tip: black, black, and black. It’s the most guaranteed way to still feel chic even if you have to wear 5 layers. Also: coordinating your hats, gloves, and boots. Make sure you’re factoring your accessories into your outfits–it helps avoid that “little kid on the playground” look. I brought one black beanie and one white/neutral beanie and I always felt warm and coordinated. And my warmest black parka. (Getting a slimmer design also helps!)
Best airport/travel outfits for long travel days and long-haul flights:
I couldn’t publish this post without touching on chic travel outfits for day-of travel. If you’ve got a long journey ahead of you, the last thing you want to wear is a pair of–gasp–jeans! The perfect travel outfit can make those long haul flights go a lot quicker, so it’s worth a bit of planning ahead.
Where to begin? Coordinating loungewear makes some of the best travel outfits. Another great combo? Comfy black leggings and a cute tee that you’ll also get a lot of wear out of during your trip!
If it’s summer, a comfortable dress can actually make a great travel outfit too (I wear the famed Amazon mumu on the plane a lot) and a bonus: a dress is likely something you’ll wear over and over during your travels to warmer climates.
Another tip: consider easy on/off shoes for airport security (or plan ahead and wear socks so you aren’t barefoot on the airport floor!)
Quince cashmere cardigan (reviewed here!) Lululemon leggings (although for a long flight I’d choose something less supportive, like their Align leggings or my fave budget-dupes, the Aerie offline leggings), Bombas socks, Kizik Lima sneakers, Lululemon city adventurer fanny pack, Amazon baseball cap
An oldie but goodie–this is still a go-to outfit formula for me: striped tee (this is my fave), loose cardigan (I love Quince’s cardigans for staple sweaters–great quality for the price!), and comfy black leggings. I also love my Delsey Paris Chatalet suitcases (reviewed here) if you’re looking for a suitcase recommendation!
WHEW, you made it to the bottom! I hope you’re feeling much more prepared for your trip. Now you know how to look stylish on vacation no matter where you’re going! Safe travels and have fun!
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