The 12 Items of Clothing I Always Pack.

Posted on
May 13, 2010

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?).

    Where to buy: Anywhere. Really. You probably have six of these already in your closet.

    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).

  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.

    Where to buy: American Apparel. And that’s the only thing you should get there.

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

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

  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.

    Where to buy: Nordstrom, Anthropologie, or your local thrift store (seriously).



  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.

    Where to buy: Anywhere. Just go for dark, solid washes with no weird lightening.

    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.

  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).

    Where to Buy: Anywhere. Ann Taylor Loft and Old Navy have some great inexpensive options, if you’re stumped.

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

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

  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.

    Where to Buy: Check out the selection of Clarks or Ecco at

    I am so buying these.

    I am so cheating on my Converse with this pair.

  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.

    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.

    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.

  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.

    Where to Buy: I like Biviel, Gentle Souls, and Sofft. And like I noted above, I’m a Zappos loyalist.

    Hello, lover.

    Hello, lover.

  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.

    Where to Buy: Basically anywhere. But I’m a sucker for Anthropologie.

    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.

  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.

    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.

    We ladies know how to accessorize.

    We ladies know how to accessorize.

  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.

    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.

    My dear friend Lisa and I in our scarves.

    My dear friend Lisa and I in our scarves.

  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.

    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).

    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.

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.

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