Someone recently asked me for some tips on fun, travel-worthy outfits to wear on planes. That incredibly elusive combination of stylish and comfortable. And I won’t lie: that is a very, very difficult balance to achieve, but I’d like to think that maybe, just maybe, I’m on my way there.

I’ll tell you now – I’m absolutely no good at coming up with outfits that would work for everyone, especially since so many of you gals out there insist on wearing skinny jeans. I can not wear those. My hips were designed by some miserable higher power with one thing, and one thing only in mind: to ensure that I will never be able to wear skinny jeans (I bet you thought I was going to say childbirth, huh? Don’t be stupid). BUT, I am great at coming up with lists, and picking out some great pieces that will help you put together stellar outfits. They’re perfect to wear on a plane, and are great must-haves for any trip you take. In fact, I can’t remember when I left home without most of these items securely packed into my suitcase.

So I sincerely hope this list helps all of you. Even those of you who can wear skinny jeans. Sigh. Like you need any help.

  1. The little black dress. Yes, yes, it’s ubiquitous, but it is so for a reason – because it’s absolutely perfect for any occasion.  Pair it with sandals for a walk along on the beach. Add a pair of fun heels and wild jewelry for a night out. Or simply pair with a blazer for a professional event (I’m speculating here. I’m unemployed, remember?).
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    Where to buy: Anywhere. Really. You probably have six of these already in your closet.
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    These two lovely ladies were at my wedding (the one on the right is my doppleganger, I know).

    These two lovely ladies were at my wedding (the one on the right is my doppleganger, I know).

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  2. The pencil skirt. The most essential and completely underrated piece of clothing in any woman’s closet. Seriously, what other item of clothing is so damn versatile (you can dress it up or down, just based on your shoes and choice of a top), and makes you feel a little bit like Joan Holloway (nee Harris) when you wear it? American Apparel actually makes a version out of jersey material, and it’s brilliant: the fold-over waist transforms it from knee-length to just above, so you essentially have two skirts in one (provided you can afford to have two-layers of fabric covering your waist. Which I’ve just decided, I cannot). Be warned, though, AA’s sizes are completely heinous. I wear a size Large or Extra-Large in their clothing. And I’m a size 6 (on a bad day). WTF.
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    Where to buy: American Apparel. And that’s the only thing you should get there.
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    This is the LEAST whorish photo I could find. Thanks, American Apparel!

    This is the LEAST whorish photo I could find. Thanks, American Apparel!

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  3. The statement jacket. I recently had a revelation. A stupid, obvious, life-changing revelation. If I simply swapped my dingy old hoodie with a tailored little jacket, I looked instantly more dressed up. And I was essentially just as comfortable. Plus, the jacket proved more versatile over the course of my trip (I could wear it over dresses, with skirts, and over jeans without looking like a hobo or an over-aged college student). It has, sincerely, changed my entire life. Which may either be very inspiring, or very depressing. Either way, I look better.
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    Where to buy: Nordstrom, Anthropologie, or your local thrift store (seriously).
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    Want.

    Want.

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  4. The dark jean. My husband will frequently ask me where my pants have ended up. Because where as most people like to take off their shoes to get comfortable, I like to take off my pants. Fortunately, I have learned that this is not entirely acceptable behavior around guests, and manage to keep my trousers on until after they leave. Why am I bringing this up? Because jeans are more comfortable than pants. And if you get a dark wash with a slight bootcut, they will look nearly as professional and polished as trousers, with less of a chance that you’ll tear them off mid-flight.
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    Where to buy: Anywhere. Just go for dark, solid washes with no weird lightening.
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    If you are endowed with a wide fundament, like myself, I suggest Pine IVs. They make your ass look like a peach.

    If you are endowed with a wide fundament, like myself, I suggest Pine IVs. They make your ass look like a peach.

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  5. The cardigan. I don’t know why it took me forever to warm up to the idea of cardigans. Perhaps because I immediately associated them with sweater sets (which, let’s be fair, are totally unholy), I shunned them for years. But cardigans are brilliant – elegant, flattering, and they can be worn more than once – a  necessary quality for something taking up space in my suitcase. Layer one under a jacket for added warmth (because planes are freezing and weather reports LIE).
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    Where to Buy: Anywhere. Ann Taylor Loft and Old Navy have some great inexpensive options, if you’re stumped.
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    My gorgeous Auntie P. shows how great a cardigan can look.

    My gorgeous Auntie P. shows how great a cardigan can look.

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  6. The dressy sneaker. It is hard for me let go of my Converse, and I suspect I’ll never truly say good-bye (somewhere is my closet is a pair I’ve had since the 7th grade. I intend to be buried in them). But alas, sometimes you need to dress things up – just a weensy bit. And frankly, Converse (and sneakers in general) can’t do double-duty – wear them with anything but jeans, and you’ll look like someone stole your luggage. Enter: the dressy sneaker. Comfortable enough to wear all day, and dressy enough that you can wear them with nice trousers and a jacket without looking like you suffered an ankle injury … or head trauma.
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    Where to Buy: Check out the selection of Clarks or Ecco at Zappos.com.
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    I am so buying these.

    I am so cheating on my Converse with this pair.

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  7. The cowboy boot. Am I insane for even suggesting something as trendy as this? Perhaps. A little bit. But hear me on this: cowboy boots are brilliant. I usually wear mine on flights, so they don’t crowd my suitcase (and they slide right off when I’m going through security). They can be paired with all manner of dresses (from summer to cocktail) and the heel is usually low enough that you can actually walk in them. Plus, they fit perfectly under boot-cut jeans (hence the name). Or, for you miserable lot who can wear them, cowboy boots can fit over your skinny jeans. There. Don’t say I never gave you nothing.
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    Where to Buy: I got mine from Nordstrom Rack (they’re made by Frye). Check discount stores that now summer is approaching – you might find some deals.
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    I bought found these at the Rack in a hideous color for 60% off. So I dyed them myself to something akin to the picture.

    I found these at the Rack in a hideous color for 60% off. So I dyed them to something akin to the picture.

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  8. The colorful flat. A co-worker once said that she started wearing flats after she saw me do it. Before then, she considered them too casual. This will forever be a point of pride for me – that I was able to change someone’s opinion about a whole style of shoe. And with good reason, because flats are awesome. They’re exceeding comfortable, which is important when you need to do a lot of walking in a new city. They slip right off, which is great in the security line. And they add a bit of life to any plain outfit – especially when you pick a pair with some color.
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    Where to Buy: I like Biviel, Gentle Souls, and Sofft. And like I noted above, I’m a Zappos loyalist.
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    Hello, lover.

    Hello, lover.

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  9. The holy-crap-that’s-awesome blouse. Let’s face it: historically, blouses have sucked. Even the word, “blouse,” is pretty lame. It rhymes with mouse.  And it brings to mind over-sized floral disasters that your friend’s mom wore in middle school (before she had that mid-life crisis and started dressing like a slut. Which was awesome for your friend, because after said crisis, she got to borrow mom’s clothes). But recently, I’ve noticed a new wave of blouses that are, frankly, awesome. Flattering styles (like empire-waists, ruched, or wrap-arounds that look great on everyone), bright colors (so they go with any basics you’ve got in your bag), and versatile enough to wear with shorts, pants, jeans, or skirts.
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    Where to Buy: Basically anywhere. But I’m a sucker for Anthropologie.
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    Pro: Its adorable. Con: Its expensive. Conclusion? My love-hate relationship with Anthropologie goes on.

    Pro: It's adorable. Con: It's expensive. Conclusion? My love-hate relationship with Anthropologie goes on.

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  10. The who-cares-what-else-you’re-wearing jewelry. I am a magpie. If it’s shiny, I fluttered right over to it. I can’t help it. I love jewelry. Inexpensive, huge, colorful jewelry. It’s my $18 a month habit. I need help. But let’s face it: accessories make an otherwise boring outfit amazing. A plain t-shirt and jeans suddenly becomes a statement. And they take up virtually no room in your suitcase. So if you’re prone to overpacking, start with your jewelry roll.
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    Where to Buy: You don’t own any already?! Sigh. Forever 21 and H&M have loads to chose from, and it’s all stupid-cheap.
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    We ladies know how to accessorize.

    We ladies know how to accessorize.

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  11. The wrap. Or the shawl. Or the pashmina. Whatever you want to call it, big, thin, wrap-them-three-times-around-your-neck scarves are awesome. They brighten up any outfit while actually serving a purpose – they keep you warm. Drape one over your shoulders with a summer dress. Place it over your eyes to block out light on a red-eye flight. Or toss one dramatically around your neck and make tasteless jokes about Isadora Duncan (I do this often. I am going to hell.) Rarely has something so inexpensive been so damn useful.
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    Where to Buy: Anywhere. Street vendors seem fond of carrying these, and with good reason. Oh, and now Old Navy has a pretty good selection, but I usually wait until their on sale. More than $6 for a scarf is too much.
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    My dear friend Lisa and I in our scarves.

    My dear friend Lisa and I in our scarves.


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  12. The over-sized handbag. On our last trip, a friend of mine stared blankly at my bag. “That,” she said, “cannot be your purse. What is that?” Clearly, my huge shoulder bag had her reeling. But when I travel, it’s a must. I can fit everything I need – water, snacks, a camera, my phone, and a dozen other things that I absolutely will not leave home without. Pick something rugged that sits well on your shoulder (and switch arms so that you don’t kill your back). A zippered top and a cross body strap (to deter theives) are musts for me. A slash-proof strap is a bonus.
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    Where to Buy: I love discount stores, because frankly, I don’t really see bags as “seasonal” anyway. Try T.J. Maxx or Ross for huge selection and good deals. If theft-proof is a must, check out Pacsafe’s line of bags (but unfortunately, I don’t find them that cute).
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    Me and Auntie P. show off our cross-body bags - these are smaller by my standards.

    Me and Auntie P. show off our cross-body bags - these are small by my standards.

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So that’s it – the contents of my suitcase – and sartorial soul – laid bare. Ideas on what to wear on flights, what to pack in your bag, and what to buy.

Now, if you’ll please excuse me, I have to go shopping.

Full list of categories:  Advice » Packing » Somewhat Useful Info » Top Ten
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Comments (24)

  1. 13. May, 2010 / Jen Nausin:

    I have that H&M necklace. I call it the Fruity Pebble Necklace and every single time I wear it I get compliments on it. Love it. p.s. I told you we were twins!

    [Reply]

    Everywhereist Reply:

    No no no no no. IMPOSSIBLE. I ALSO call it my Fruity Pebble Necklace.

    Then again, it really DOES look like Fruity Pebbles.

    [Reply]

  2. 13. May, 2010 / philip:

    I have found that a blazer and a good pair of jeans will get you just about any place. And shoes without laces (don’t just take the laces out, buy some good slip-on shoes) Of course, I almost always have to pack a suit and that’s always a pain in the ass, but it does force me to try to fit everything into a garment bag. I’ve thought about investing in some wrinkle-free shirts, but I haven’t found any that don’t scream “douchebag!” Maybe that’s just me. I’m judgy like that.

    Would love to get your well-traveled spouse’s take on his must-have garments for the road. I want to be like him when I grow up.

    Also, thank you for the American Apparel comment. Their whole site looks like the first 10 minutes of a porn flick. Not that I’d know anything about that.

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  3. 13. May, 2010 / Deanna:

    Question for your next round of advice: what kind of jewelry roll do you use? I am ever so slowly getting over my fear of the bright and shiny (I know, I know) but this is the one group of items I have no idea how to pack. I seem to be going full-throttle for the big chunky necklaces. And though it should just make sense to leave the valuable stuff at home, I don’t want the cheap stuff to get snatched either–what do you do about security?

    Also, skinny jeans are of the devil. If I wanted to look like a weeble wobble, I would totally wear them, but I do not.

    [Reply]

  4. 13. May, 2010 / Everywhereist:

    Deanna – At first, I was very confused when your comment appeared in my email. Because of how my email loaded, I thought it was coming from Philip. And I thought – he has A LOT of explaining to do. :)

    As for jewelry rolls, I have a plain, silk jewelry roll that I take with me (similar ones are available at Storables: http://www.bedbathandbeyond.com/product.asp?order_num=-1&SKU=16484458). I usually can fit a few huge pairs of earrings in mine, and perhaps a necklace. Anything absolutely ginormous I wear on the plane. As for security, I just make sure it’s deep in my suitcase in case someone snoops through my hotel room. Unless my entire bag gets stolen, my jewelry won’t.

    And the good news is, if cheap stuff is stolen, it really IS replaceable (trust me – it’s happened before.)

    [Reply]

  5. 14. May, 2010 / Candice:

    Maaaaan, I love that jacket. MUST HAVE.

    I swear by flat shoes. They’re a godsend. They can be super dressy too, and easy to pack.

    [Reply]

  6. 14. May, 2010 / Candice:

    OH, and I also have a habit of taking off my pants wherever I go!! It’s awesome. As soon as I get home, my pants are off and stuffed in the hamper.

    [Reply]

    Everywhereist Reply:

    Candice –

    You stuff them in the hamper? Weird. I leave them in a pile on the floor.

    [Reply]

  7. 14. May, 2010 / Jen Nausin:

    Get out of my dome, dude. It’s freaking me out.

    [Reply]

  8. 14. May, 2010 / Katie Hammel:

    Great list! I too have that necklace, love flats (which is recent – I used to be a heel whore) and take off my pants as soon as I walk in the door.

    Also, thanks for letting me know that I never need to set foot inside an American Apparel – not that I thought I should, but a size 6 is large or extra large? They’d probably chase my size 8/10 ass out with pitchforks and torches.

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  9. 14. May, 2010 / JoAnna:

    I agree completely with numbers 10 and 11. Bring on the chunky jewelry … and don’t forget to bring something to keep warm on the airplane!

    [Reply]

  10. 14. May, 2010 / Laura Z:

    Fantastic list! I think these all make great eveyday outfits too. I totally need to get myself a statement jacket!

    [Reply]

  11. 14. May, 2010 / Everywhereist:

    Laura – you HAVE a great statement jacket! I know, because I’m the one who’s responsible for you buying it. :) I actually almost included a photo of you wearing it in the round-up, but couldn’t find a clear enough pic.

    [Reply]

  12. 14. May, 2010 / Shannon OD:

    You have inspired me with the jacket! It’s too cute and I hate how slummy I look with my nubby hoodie on the road – brilliant tips!

    [Reply]

  13. 16. May, 2010 / Kristina:

    I pack almost everything on your list when I travel, though destination does make a difference. All of that works for Europe, but jeans and the little jacket (which I love too) are too hot for South East Asian destinations.
    The only thing I can’t do are the flats. I’m short so they just make me look shorter (IMO). I also have high arches. I’ve never found a pair of cute flats with any kind of arch support in them.
    The one thing on your list I always bring is a cashmere sweater (which could count as the cardigan I suppose). I like cashmere because it’s really light and can be squished pretty flat in a ziplock bag, but is also very warm. They can be found pretty inexpensive these days at places like Ross, Marshall’s, and even Costco (usually around xmas).

    [Reply]

    Everywhereist Reply:

    Kristina –

    You are totally right – this list works for in colder environments. It sounds like you have a lot of experience with warmer climates (and if I can pester you into writing a guest blog post about what to pack for South East Asian destinations, that would be AWESOME! :)

    I have a lot of trouble finding flats with arch supports, too. Born makes a few with some support, as does Gentle Souls (of course, they make many more with zero support). You might want to give them a try.

    And – gasp! – cashmere to travel? I like the way you think. :)

    [Reply]

  14. 16. May, 2010 / Kristina:

    Yes, I have a thing for SE Asia (5 trips in last decade and going back in October). But Europe is ahead with 7 trips, so Asia has some catching up to do. ;-)

    I’m actually a bit of a packing fanatic (specifically packing light) and have 4 pages dedicated to it on my site, starting here http://www.wired2theworld.com/travel-tips/packing/ and including packing lists for both hot and cold weather trips.

    Email me if you want to talk about a guest post.

    [Reply]

  15. 16. May, 2010 / Trisha Miller:

    Excellent list! Funny too – I’m also a pants-tosser and costume-jewelry addict….but I organize my accessories by outfit, and then put them into separate little sandwich baggies, and then put all the sandwich baggies into a large ziploc bag. And it may all be cheap, but it’s mine so I keep it in the hotel safe, unless I’m visiting my family, in which case I hide it under the bed pillow. My sister sometimes ‘borrows” my things and “forgets” to give them back.

    [Reply]

  16. 17. May, 2010 / Christine:

    I love this list! It’s also a pretty accurate list of items a young professional woman needs for “business casual” attire, IMHO. I’m kind of a pants tosser, but really I’m more of a pajama wearer than anything else. Jason knows that I can’t really help with anything when I get home from work until I’ve changed into PJ’s.

    p.s., I have that Anthropologie blouse. Love it.

    [Reply]

  17. 11. Aug, 2010 / Bailey@peppermintbliss:

    “Endowed with a wide fundament” might be my new catchphrase.

    [Reply]

  18. 19. Nov, 2010 / Ashlea:

    I’m taking all of these tips into consideration when packing for my next trip. The link to American Apparel also provided me with a few laughs. Then the link to Anthropology made me feel depressed and poor. It balanced my mood.

    [Reply]

  19. 06. Apr, 2012 / Katie:

    Hi, I just found your blog a few days ago and really enjoy it. I already wear most of the things you listed, but I am a HUGE

    [Reply]

  20. 06. Apr, 2012 / Katie:

    Sorry that last comment sent before I finished and can’t delete it, but I just wanted to tell you I recently found me too flats. They are great they put memory foam in the souls for all day comfort and have a lot of cute styles. Sorry for the comment hiccup, computers don’t seem to like me much.

    [Reply]

  21. 07. Oct, 2013 / Ciara:

    This is a fantastic list. I am a little obsessed with onebag.com for packing methodology, but this is really helpful in a different way.

    [Reply]

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