outfit posts: reader request - how to travel for business

I just got my first reader request from Ashley who is about to take a work trip for her new job.

Here's her question:
I have a reader request... FAQs for traveling for business! 
-packing in one carry on
-what do you usually wish you had?
-eating while traveling
-anything else!!! :) 

I'm going to try to walk through my method for preparing and packing for a business trip. After so much travel in the past few years - I feel like I've finally gotten comfortable with easily packing a carry on bag for up to three weeks of supplies for a range of activities into a totally easy to manage load of stuff.

  • Make a list of activities of what you'll be doing on the trip. A typical list for me would be something like:
    • Travel Day - Drive, Flight, Hotel
    • Work Day One, Co-worker Nice Dinner
    • Work Day Two, Sightseeing
    • Work Day Three, Co-worker Bar/Club
    • Work Day Four, Co-worker after work session at hotel
    • Work Day Five,  Sightseeing
    • Tourist Day - Lots of walking
    • Travel Day Home - Flight, Drive, Home
  • Then I turn it into categories:
    • Travel (x2)
    • Work (x5)
    • Tourist (x3)
    • Nice Dinner
    • Bar/Club
    • Casual Clothes
    • Hotel Room Comfy Clothes
    • Gym/Workout
  • I like to make copies of all my travel docs & travel info and leave them with my parents or hubby:
    • License and/or passport
    • Flight info 
    • Hotel info
  • I then run some errands:
    • ATM - to have some travel cash - at least $100
    • Drug Store - Any small toiletries I have figured out I need (I'll go through list below)
  • For each activity I have (above) I try to pick my favorite go-to clothes. Clothes I know I wear over and over. This usually involves starting off by laying out my black work pants, favorite jeans and super comfy flats. And then I move to each activity's clothes:
    • Traveling Outfit - I usually wear the same thing to and from my destination. I like to look above average cute in the airport as well as be comfortable. That means the outfit has to deal with hot airports, cold airplanes and hours of sitting. I also try to pick the largest clothes to wear so they don't take up room in my suitcase.
      • My most likely outfit would be -
        • Jeans, Non-wrinkle Shirt, Flats/Boots

      • I recently scored at Old Navy and bought some polyester type shirts that totally don't wrinkle no matter how wadded they are in the bottom of your suitcase.
      •  In addition to the outfit I wear on the flight - I plan on carrying a jacket (even heading somewhere warm) and a big scarf over my arm. The jacket & scarf are great as pillows & blankets, keeping warm on arctic flights or randomly cold hotels/offices. My go to items are-
        • Navy trench coat and a black wide scarf.
    • Work Outfits - This is where I'm always tempted to over pack. Client offices can range from very formal (lawyers) to very informal (software companies) and so I always want to bring lots of options. But I've learned to limit myself.
      • For pants I usually end up bringing one long black pants (for wearing heels, usually part of suit), one short pair of black pants (for flats) and one black skirt (possibly part of suit).
      • I always bring a suit jacket, even though I rarely end up wearing it after the first day. I feel like it's respectful to the client to show up in a suit the first day - regardless of if you know it's a casual office. For lawyer-type offices I usually bring two suits that have skirt & pants options and a sheath dress.
      • I always think I'm going to wear lots of button down shirts because they look the most professional but by the second day - I am usually exhausted between traveling, talking all day and then doing my regular daily work after the all day client meetings and finding some food - so the idea of ironing the next morning gets thrown out of things I want to do. I've learned only to bring 1-2 and then rely on non-wrinkle blouses and cardigans.
      • Things I bring:
        • Favorite favorite work pants (or skirt)
        • Alternate pants option
        • Skirt option
        • 1 suit jacket
        • 1-2 button down shirts
        • Shoes - one color, one trusty comfy, one heel, one sandal
        • 4-5 Non-wrinkle tops
        • 2-3 Cardigans
        • Dress
      • My work outfits are usually have the basic formula of plain bottom, patterned shirt, cardigan. The outfits below all have tie fronts but if they didn't I usually throw in a couple of chunky necklaces to make the outfit 'complete'.
Button down (Brooks Brothers non-wrinkle - still wrinkles some in suitcases), 
favorite black pants (Express), black belt (Express), very high black heels (Charles David)
Black cardigan (Old Navy), grey skirt (part of Ann Taylor suit), 
patterned front tie top (H&M)
Top (one piece polyester, impossible to wrinkle from Limited years ago),  
favorite black pants, black heels
Suit skirt (Anne Taylor), black cardigan (Old Navy), 
front tie top (H&M - same one as above w/o pattern), heels 

Black cardigan (Old Navy), dress (Banana Republic), 
probably flats by this point

    • Hotel Outfits -  I find that after being 'on' all day at client I really really really like getting into extra comfy clothes in the hotel room. Hotels can be weird. In London my flat didn't have A/C just fans and in NYC I stayed at a fancy hotel and it was 55 degrees outside but they told me they hadn't turned the boiler on yet for the winter. So you could be really hot or cold.  I pack:
      • Warm PJs, cozy socks
      • Light PJs, tank
      • Comfy lounging around clothes (could double as workout clothes or meeting coworkers to work in the hotel or adventure touristy clothes)
    • Touristy Outfits - I usually try to combine my travel jeans with my non-wrinkle tops to make city type touristy clothes. Other times if I have a thin top that's fun for the city but not work appropriate I will pack it because it takes up so little space. And then I usually wear my flats or sandals. 
      • Reuse work tops
      • Reuse travel pants
      • 1-2 extra casual tops 
Reuse workshirt & travel jeans.
Or maybe add a few casual shirts to suitcas. 
LOVE Stripes.
    • Coworker Bar/Club/Dinner Outfits -  I can usually reuse work clothes for nice dinners. Maybe remove the cardigan that's covering a nice blouse or dress. And then for nights out on the town - I usually wear my black pants and swap my top for the day with more exiting/sparkly top and/or some big jewelry. I try to stay classic in my nighttime attire - don't need to dress overtly sexy around coworkers.
      • Work inappropriate top
      • Big jewelry - fun earrings or chunky necklace
    Out to dinner from work.
    Work pants (imagine them long) 
    plus a top you wouldn't wear to the office

    • Workout/Adventure Tourist -  I frequently pack a set of workout clothes & sneakers. But I rarely rarely ever end up using them. By the time I work 9 hours at the client, 3-4 hours at the hotel plus go to dinner to socialize with coworkers - I can usually only get 6 hours sleep. I never seem to manage adding in gym time. And I usually regret the space the bulky sneakers take up. So I've moved to admitting I'm not going to work out and making sure the clothes I pack for lounging around the hotel room would suffice if I needed to do something somewhat hiking/adventure plus my sandals. 
    • Extras - Clothes:
      • More underwear then days
      • Double check any special bra requirements (strapless? racerback?)
      • Pair of warm socks
      • Extra fun jewelry - takes up very little space  
  • Travel Stuff
    • Money, Credit Cards, ID - most important of all items to pack - as long as you have these you can make it to your destination and if forget other stuff and buy it when you arrive! 
    • Travel docs - I usually keep these (flight & hotel info) on my phone in an email/doc I can get to without internet connection
    • Entertainment - One digital (iPad), one print (Paperback, UsWeekly) - Have to bring print version of stuff because you can't have digital things running when plane takes off or lands. Unless you like the in fight magazine & skymall.
  • Personal Stuff:
    • Shower - Conditioner, Razor (I use hotel shampoo & soap)
    •  Makeup - Best tip ever is to pack your makeup the morning you are leaving. Do full on makeup for the airport and as you apply each thing put it into your makeup bag. Best way ever to remember everything and not end up far away without mascara. 
    • Misc - Tweezers, Bandaids (your feet will thank you), Nail Clippers, extra ziplock (randomly use it to organize stuff), plastic grocery bag (dirty/wet clothes)
  • Work Stuff:
    • Tech Stuff - All chargers (camera, computer, phone, etc), USB drive (thumb drive), network cable
    • Work - laptop, envelope for receipts (if have to track expenses)
  •  I travel with three bags. Airports claim you can only carry-on two bags but if your laptop case and purse fit under the seat then they will let you have three. 
    • Outer bags:
      • Carry-On size roller suitcase 
      • Big purse
      • Laptop bag
  • When I pack the Carry-On with my clothes I try to be smart and wear the bulkiest items. I also try to hide belts & socks inside of shoes. 
  • In my big purse I store my important items in a reachable (preferably zippered) pocket as well as add two ziplocks. One with liquids to pull out in security and another for all my techie stuff (chargers, mini camera, etc). It's surprising how frequently I need the tech stuff and it's great to be able to find it easily.
  • I also put my small makeup bag and ipad and paperback book in my purse. I want to be able to get to all of those things easily on the plane. I like to put things I use during the flight in my purse and things that are more 'put away' (laptop cord, notebook for client) in the laptop bag. Just helps me know where to look and not rifle around a bunch.
    • Purse Pocket - easy for you to reach, hard to accidentally dump out or get pick-pocketed
      • Phone, ID, Tickets
    • Inner purse bags:
      • Small Clutch/Wristlet - I put my wallet inside a small clutch to make it easier to find in the huge purse as well as the wristlet becomes my small going-out bag or my light & small to carry while touring around purse.
      • Tech Ziplock - chargers, cameras, USB, network cable
      • Security Ziplock - liquid
  • To carry it all I put my laptop case on top of my roller - against the handle - so it becomes one tall roller. 

  • Over my shoulder or elbow I have my purse.

  • And then over my arm I carry my jacket & scarf. (Sometimes I let my purse hang in the crook of my elbow with the jacket & scarf over it so the stewardesses won't hassle me about three bags - even though they will let you on once you explain the laptop & purse both fit under the seat in front of you.)

  • I like to be super speedy in security. To quote Dooce's expression, I like to be the Valedictorian of <fill in the blank> and for me it's security efficiency & speed. George Clooney at security in Up in the Air? Slow compared to me!
  • Here are my tricks to be lightening fast - 
    • Tickets & ID in zippered easily reachable purse pocket for first security officer
    • Laptop unencumbered in laptop bag sitting on my roller bag.
    • Shoes easily removeable
    • Liquids easily reachable in ziplock in my purse
  • As I approach the scanner (having already removed my shoes, liquids & laptop) I grab two bins and feed my stuff through in the following manner- 
    • Bin 1 - Dump my jacket, shoes and ziplock with liquids on top
    • Bin 2 - Laptop
    • Purse 
    • Still connected roller bag & laptop case
    • Keep ID & ticket in my hands
  • Don't fumble to remove your stuff as you stand in front of the bins. Don't have crap in your pockets.
  • First walk to gate to see current flight info. How much time do I have? Usually board thirty min prior for domestic and up to an hour before for international. 
  • If I have time I will walk to snack stand and buy huge water and some snacks. Snack stands have gotten pretty healthy. I usually buy fruit, cheese or nuts. Possibly a salad if it's a long flight. 
  • If I've really planned ahead (and have space in my purse) I pack myself similar snacks from home and a empty water bottle. Once you're through security you can go fill it up at a water fountain instead of buying $8 water. (I buy mostly because I'm lazy and because I get reimbursed for work travel expenses.) If you buy anything - buy water. Hate waiting for stewardess while thirsty.
  • I usually try to immediately scope out a convenience store and buy a couple of huge waters. I hate paying a zillion for water in the hotel and having clients see that item on my room bill.
  • I also try to immediately scope out a coffee source. Is there a coffee maker in the room? In the hotel restaurant? Nearby Starbucks?
Okay - that's what I've got off the top of my head. Let me know if you have more questions! 


  1. Holy cow! That is a lot of good information, so sweet for taking the time to write this down. Love your blog, very practical, to the point.


  2. I'm just going on a weekend trip, but this is all incredibly helpful! Great tips on security too! THANKS!

  3. This was all incredibly helpful! Love the idea of bringing an envelope with you for travel expense receipts. At the end of my trips, I'm usually fumbling through my wallet and laptop bag, which is entirely non-efficient.

    Thanks for sharing!


  4. Thanks for sharing your tips!!! You are a work travel pro!

  5. Thank you! I really enjoyed reading this. I'm also envious of flights that allow you to take on 3 bags...!! Easyjet and Ryanair are incredibly strict and have made me ruin a handbag by forcing me to stuff it into my carry-on luggage at security, just before boarding the plane... Then I discovered Longchamp bags and now I always fold one into my roll-on. I also wear a completely unfashionable but super-useful utility belt which security doesn't identify as a 'bag' but which doubles up as a purse-cum-handbag (yes, I overstuff it). Thanks for this!!

    1. Great idea with the Longchamp bag! Glad you found the post useful!

  6. Lol... i'm exactly the same about my workout clothes and shoes. I live in Germany and travel once a month around Europe for either work or leisure. You would think after three years I'd have it all down but I'm still refining my process. I would recommend downloading either workout videos(yoga or abs) or good picture book onto your iPad and using the hotel towel and bare feet. I don't have to bring anything extra except for some spandex shorts/capris and a tank. My next big trip (after a short work trip to Stuttgart and another to Rome) is a cruise to the Eastern Mediterranean with my sister and girlfriends. Needless to say I've already starting "mentally packing" but your list here will help me get it all down. The only saving grace for this trip is that we got great deals on Lufthansa and DONT have to fly Ryanair. So i can have a carry-on, purse AND a checked back. The key will be saving space to bring stuff back!!

    1. Thanks for the tips! I hope your trip is amazing!

  7. Thank you so much! I am terrified of flying and this list makes it seem possible. Preparation is the key.

  8. lots of good tips here! how do you handle and organize all of the dirty clothes and packing them back up? Do you bring a separate bag or use the hotel laundry service? thanks :)

    1. Sometimes I use the hotel laundry service - mostly if I'm staying a few weeks and I need to re-wear stuff. But more often I unpack my clean stuff in a hotel drawer and then toss dirty stuff into my suitcase as I wear it. The only time I've brought an extra bag for dirty clothes is when I'm changing hotels a lot on one trip - then it's nice to keep the clean & dirty clothes separate.

  9. This, and your whole site, is so helpful! thank you so much!!


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