Flop Proof Traveling Outfits

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Angie is co-founder of YLF and its resident fashion stylist.

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Outfits Ensembles Trends Advice

Flop Proof Traveling Outfits

— by Angie

on March 8, 2011

This is the first in a series of 4 posts brought to you by Nordstrom.com: Think Less Buttoned-Up—It’s a New 9 to 5.

When working with clients I find it useful to think about business travel in terms of two outfit formulas. The first of these takes you from the airport directly into a business meeting and therefore professional garb is a requirement. The second outfit takes you from the airport to a casual setting, like your hotel room.

Career Wear: Plane to Meeting

Non crease top: The Kenneth Cole New York sleeveless blouse ($69) is ideal. Sleeveless tops layer exceptionally well and the pattern helps hide stains incurred during the day. Brook’s Brothers non-iron miracle shirts are another great option and a personal favourite.
Comfortable bottom: Pencil skirts aren’t generally something you’d associate with comfort, but the Halogen seamed knit skirt ($68) looks professional and is very comfortable because it’s soft and stretchy. If you’re a trouser gal, try the Sloan fit black textured flare. It’s just as soft and stretchy – fits like a dream.
Jacket: Ann Taylor’s Bergman tweed two pocket jacket ($144) is a great mixture of both classic and fashionable edge. It is single breasted, seasonless and looks just as good un-buttoned. Fab with dressy bottoms or a pair of faded jeans.
Cardigan: This is an optional extra, but on the plane you can take off your formal jacket and pull on a cozy cardigan for the flight. The Halogen long sleeved boyfriend cardigan ($69) looks great with dressy bottoms and might even be sufficiently professional to wear during your business meeting. Personally, I would swap out the cardigan for my jacket as soon as the plane landed because nothing says you mean business quite like a tailored jacket.
Pumps: Comfortable heeled shoes are a must. Choose something with a cushioning foot bed that’s easy to slip off and on for the security check. Although Sofft’s Ramona patent pump ($109.95) is too high for me, it’s received great reviews and is well worth a look.
Large Tote: It’s practical to carry a tote when travelling, large enough for handbag essentials, a few notes and possibly a laptop. The Halogen metallic leather tote ($98) is a dream. It’s simple, chic, lightweight and available in lots of colours. You can even carry a small handbag along with the tote it that suits you better.

Casual Wear: Plane To Hotel

Oversized top: A big blouse, denim shirt, voluminous knit top or roomy pullover are great casual top travelling options. The Alternative melange burnout dolman sleeve tee ($42) is fabulous and looks amazing with a scarf.
Scarf: I like to wear scarves on flights because the arctic air conditioning blasts freezing air and I’m always cold. My favourite types of scarves are pashimina size, patterned, and very soft, like the Halogen paisley dot challis scarf ($38). They drape well and add just the right amount of polish to a casual outfit.
Cover up: It’s a good idea to bring along a jacket, cardigan or trench coat to combat the cold air on a flight. Topshop’s black classic belted trench coat ($160) is a versatile solution since it can be dressed up or down for your trip.
Jeans: Comfortable jeans like Gaps’ Real Straights ($69.50) are ideal because they’re stretchy. Knit Ponte pants or legging jeans are nice alternatives.
Ankle Boots: I like to wear closed shoes with socks when I travel because it’s cozy and comfortable. Ankle boots like Frye’s Short Taylor ankle boot ($338) are my go to travelling choice. I have these in Fawn and they are wardrobe workhorses.
Large Handbag: Choose a large handbag like Fossil’s Modern Cargo leather shopper ($188) so that you can pack extra stuff. A gal needs all her goodies when she’s away from home.

During my fashion buying days, I travelled in business casual most of the time because I had meetings with manufacturers and management as soon as I got off the plane. Now that I’m my own boss, I can travel in casual comfort and change into another outfit for business meetings.

I’m not in the habit of traveling light, but if you are then you might want to pick the career wear option even if you’re not going directly to meetings. That way you can minimize your traveling wardrobe and pack everything in your cabin luggage if your trip is only a few days long.

Are you are a regular business traveler? If so, what are your traveling outfit strategies?

39 comments · Add a comment

Moni

I love to travel in a jersey or ponte knit dress. Throw a cardigan over it and its comfortable for the plan, just like wearing a nightgown! Switch it out for a blazer (or keep the cardigan, depending on how formal you need to be) and you’re business ready.

March 8, 2011 at 6:00 am

Barbara

Veteran

Fabulous post, Angie!

I agree with Moni: Knits are my best traveling companion. Most of my traveling has been flying to and from Europe for pleasure and my knitwear has NEVER let me down.
I hope to be visiting Italy this fall!

I LOVE the outfits you posted. Great inspiration, just like your previous ‘what to pack’ post.

March 8, 2011 at 6:07 am

Sarah

(website)

Active Member

Great ideas. I love your casual suggestions. I’m not a business traveler, but I do fly overseas once a year to visit family. After a 7 hour overnight flight plus a connecting flight, I’m usually feeling pretty scruffy by the end no matter what, but dressing better does make a difference. I used to go for extreme comfort and wear yoga-style bottoms and hoodies with sneakers/trainers, but I learned I actually feel *more* comfortable when I dress better. It’s not a good feeling to arrive at your destination sleep deprived AND looking like you just rolled out of bed!

March 8, 2011 at 6:17 am

Lisa

Veteran

Great post. When I travel for business it’s always in a suit. The blazer of a suit is my largest and hardest to iron piece. I’d rather not have to worry about ironing in the hotel. I also wear my trousers and pack the skirt. For more than one day swapping out the trousers for the skirt is easy and the skirt is smaller and easier to both pack and iron out wrinkles quickly.

Layering and a large tote are key for me on the plane. I’m always cold and having a large scarf or pasmina also acts as my blanket on a flight. Or I can ball it up as a pillow in a pinch. The large tote always has a smaller bag in it, which makes it easy to grab the essentials for a meal out without the bulk.

For casual travel I favor a large cardigan, the soft styles make me feel warm and cosy. And I am a fan of socks and shoes or boots over bare feet. I don’t like to walk on the airport floor sans socks for security checks. And I always wear jeans, again they are one of the heavier items I will pack (versus say a skirt) and keep my legs warm on the flight.

I am really not a fan of travel with loungewear. I know people want to be comfortable but I don’t want to feel like I am seeing you straight from your bedroom. There are ways to be comfortable and be “dressed.”

March 8, 2011 at 6:37 am

Angie

(website)

Fashion Stylist

Wow, Lisa. You have got it down! I’m impressed.

Syrah, I see lots of people wearing loungewear at the airport and in the plane. Kids too. I’m glad you feel more comfortable in an outfit a few notches up from that.

Moni and Barbara, good point. Knit dresses can be our traveling friends too. I have a few clients who like to wear knit dresses with leggings on flights and it works beautifully for them

March 8, 2011 at 6:49 am

Sparky

Veteran

How funny! I ordered the Kenneth Cole blouse last week and it’s on its way to me. I’m a SAHM and just looking to add more blouses to my wardrobe, so I think a top like this works equally well for casual settings.

I used to travel overseas a lot for work, and my suitcase held two sheaths, one blazer, one cardi, one pair of black trousers and a button-up shirt, plus two pairs of shoes and two scarves. That was enough to get me through two weeks of meetings. My traveling outfit for the long haul flights was jeans plus cardi plus short-sleeved sweater top that matched the cardi (yes, the cardigan twin set) along with a scarf. While casual, I still felt polished, which I absolutely prefer while flying.

March 8, 2011 at 6:51 am

rae

(website)

Veteran

I don’t fly for business, but this is good information for anyone with an important impression to make straight off the plane. Many times, I walk off a flight to be greeted by in-laws-to-be, so I don’t want to look a mess. Thanks, Angie!

March 8, 2011 at 6:59 am

Laura

(website)

Veteran

I’m one of those who loves to travel in dresses and leggings. It’s so comfy! Does anyone else tend to get stomach issues on a flight, especially when wearing jeans or something binding? Maybe I’m unusual that way.

While I swear that planes used to be freezing most of the time, I now find that they are overly warm. Even if I’m wearing boots and socks, I like to bring ballet flats in my carry-on, in case my feet swell.

March 8, 2011 at 7:04 am

JvA

Those Fryes are adorable–another pair for my wish list!

Hey, I was wondering if you’ve looked into the chemicals behind wrinkle-free/no-iron cotton wovens. I’ve heard things like the cotton is treated with carcinogens like formaldeyde, and it may be personally unhealthy to breathe in, as well as dangerous for marine life when you wash the garments and the chemicals get into the water. I haven’t done my research yet on this, but I’ve just been avoiding buying these fabrics until I do.

However, my goodness, I loathe ironing. And I recently chose an entire set of normal cotton napkins over the wrinkle-free ones, and let’s just say I may never have another dinner party again…

March 8, 2011 at 7:33 am

Carole

Veteran

What a timely post for me…I was just putting together a travel capsule last night for my upcoming Paris trip! I’m planning to take my black trench and plenty of scarves, I get cold too! It’s fun to see the Frye short boots in your traveling outfit…I would love to have those, I just think they are a little too high for me. I wonder if they have a shorter heeled version?

March 8, 2011 at 7:37 am

Diana

Veteran

Caveat: I don’t work in a business environment and almost never need to be in business wear (casual or otherwise). That said, my go-to plane outfit is a comfy jersey dress plus leggings if it’s not summer. I also usually have a cardigan and a big pashmina shawl in my bag. I actually prefer my leggings in this case to be slightly too large or a little stretched out since it’s more comfy and nobody can tell if my leggings are sagging under the dress anyway. I usually wear boots as well (again, unless it’s summer) but this is mostly because I like to travel super light, which means wearing my biggest shoes on the plane. Plus, big boots with socks are comfy!

March 8, 2011 at 8:13 am

Aunty

Veteran

Thanks Angie, brilliant ideas for when I go away for a few day’s in June.
I had thought skinny jeans, boyfriend jacket and a comfortable top. I am keeping fingers crossed that by then I will not need boots, so the ballet flats could be comming out to play.
I much prefer a polished look because if I am “people watching” they might be watching me!

March 8, 2011 at 8:17 am

Debbie

Veteran

I love traveling in a dress and leggings with a scarf and big tote. Especially on a long flight.

March 8, 2011 at 8:24 am

Encore

Hi All! – I am now retired and developed a casual travel uniform which works great for me.

Jones NY Stretch Black Jeans, AT Loft crisp wrinkle free white blouse, black sweater, red patterned scarf, my ever faithful/comfy/ Geox burgundy slips on loafers, either gold or silver jewelry (depending on which specs I wear). If I am traveling to cold weather destination, its my black winter coat and if warmer climate than I take along a lightweight check patterned Jones NY 3/4 jacket in cream and black.

These items have passed the security test of easy off/easy and the stretch in the pants are perfect and most if not all, are wrinkle free so I don’t feel too scruffy after a 11 hour flight to Europe or longer flight to Asia.

I also take along a black Longchamp tote for books, journal and yoga pants to change into while in flight if needed.

My travel outfit is pretty straightforward and has all the basics of any wardrobe (travel or not) so I haven’t had to buy anything new!

March 8, 2011 at 8:31 am

Active Member

This is such a timely post for me, as we will soon be flying coast to coast on vacation! I definitely have been guilty of dressing too casually in the past. I always feel better if I look better.

But I, too, find even comfortable jeans too binding on a long flight, like Laura. I’m not really a leggings gal, but I think I will wear my ponte knit pants, loose top and boyfriend cardigan. I will probably wear ballet flats with those, but stash some warm slippers or slipper socks in my carry on. My feel always get cold!

March 8, 2011 at 8:42 am

Antje

Veteran

Great post. I’ve travelled quite a bit for business (as well as tons for leisure). Most of the time I schedule my flights so I can stop at the hotel and change, but occasionally I’ve had to go straight from the airplane to a business meeting. In that case, my outfit would be similar to the business outfit you describe above, except that I’d always travel i n pants (dark dressy pants like the Editors from Express). I want to be really comfy on an airplane, and while I love pencil skirts, they are just too fussy for me when sitting next to who knows who and trying to get comfortable. The shoe recommendation is right on; I have two pairs of super comfy (and lower-heeled) Me Too pumps that I wear as part of business outfits. I always wear shoes (also when travelling casually) that I can easily slip off, and usually have a very light weight pair of slippers with me that I can change into during the flight, e.g. those free bath slippers you get in hotels sometimes. Shedding my shoes makes a big diff to me comfort-wise.

Finally, I have to make a plug for my rolling laptop bag, which is so awesome as it fits everything I need (laptop, notepads etc. for work, as well as personal items like a book and the aforementioned slippers), rolls super well, and is very sturdy and high quality. It really is a business woman’s best friend, not just for air travel but also if you have to walk a bit once you’re at your destination, e.g. to a meeting location or walking around a trade show. No more sore shoulders from lugging heavy bags around! Not sure if this one is exactly the one I have, but it looks very similar. http://www.ebags.com/product/m.....d=10014852 Ebags has lots of nice rolling laptop and I highly recommend checking them out if you travel frequently for business with a laptop and other “gear”.

March 8, 2011 at 9:10 am

rute

Veteran

Great post! Lovely outfits!

March 8, 2011 at 9:31 am

Lynne

Veteran

I adore that Fossil tote….it looks perfect for my MOTG stuff, too!

March 8, 2011 at 9:46 am

Joy

Veteran

I don’t travel for business but have found that if I look like a business traveler, I have a good chance of being bumped up to business class. This was especially nice on my last trip to Europe. I’m also finding that planes can be too warm, especially if you are delayed sitting on the tarmac and the air isn’t running. Layering is the way to go.
I like to travel, like Antje, in dark slacks that have some stretch but won’t get baggy. On top I layer a silk tank under a buttondown blouse or shirt under a jacket of some sort. I wear small heels from Me Too or cute metallic flats with those knit peds to prevent having bare feet in the airport check in. The peds can also serve as slippers. For extra warmth and suitcase room, I carry a trench and often have a pashima too.

March 8, 2011 at 10:14 am

mamark

Active Member

This is great advice, Angie. I travel on business quite frequently and I use your strategy in the first post quite often. I almost never pack my blazer if I don’t have to, because of the potential wrinkling. A word to the wise – TSA will make you take your blazer off at security, so if you hate your arms or have bra straps showing, know this. It was an issue for me once because I was traveling with colleagues, and I felt quite naked with my jacket off.

I have found myself doing quite a few day trips lately (fly from SF to LA in the morning, home in the evening) and it makes for a really long day. I slip a pair of collapsible ballet flats into my tote for the trip home because by the time I’m catching that 6PM flight (after getting up at 4AM to catch the 6AM flight) my feet have absolutely given out.

I also pack a pashmina even if it’s a trip into warm weather, because airplanes are so cold most of the time.

Airlines are not reliable for giving out snacks anymore so I usually have a Kind bar or a Luna bar in my bag. I also make sure I have some ibuprofen or tylenol because for some reason, air travel tends to give me a headache.

For really nice looking totes that double as laptop cases, check out Jack Georges. The leather is really nice and they look much more fashionable than the ubiquitous black nylon laptop cases.

I usually don’t bother putting on my jewelry until I’m through security. I keep it in a drawstring jewelry case in my purse or tote.

Lastly, I’m finding it much easier to travel without my laptop these days, now that smartphones can do so much. They can’t do the number crunching that is my job, but for a day trip, there usually isn’t much time for that anyway. What I’m saying or recommending is, really think about whether you will actually need that laptop! By the time you pack your laptop and the power cord and all the accessories, your tote can become really heavy.

March 8, 2011 at 11:22 am

Alecia

Veteran

Great post, Angie. I don’t have to travel for work often but do have to do it from time to time. Most of my flights are short trips within the state (no more than an hour) and so I don’t do anything different than I would otherwise do while dressing. The only exception is footwear. I try to put together an outfit that will allow for shoes that slip on and off easily for the security lines.

For the cross-country trips, I put more thought into it. I am often cold so shoes with socks are a must (and again, ideally I make them slip on shoes but that doesn’t always work since in trying to keep packing light, I may wear the bulkiest footwear I bring – boots). I also always carry a pashmina for the wrap/pillow function. Having comfortable bottoms is a must. This usually means pants with some kind of stretch. I just got some very nice pants at Talbots that I think will be my go-to travel pants. They look tailored but have stretch and are also machine washable (the holy grail!) My top have is less of a concern. I usually wear a blazer, which allows layering and looks sharp.

These Talbot pants aren’t the ones I have but I think they’re kind of similar? http://www.talbots.com/online/.....e=cat70008

March 8, 2011 at 11:39 am

lyn*

(website)

Veteran

I do adore that Fossil bag, Angie … now I have my heart set on it

March 8, 2011 at 12:29 pm

klauren

Active Member

While I don’t travel often for business, I do for other events and fun! So these tips certainly help, however there’s a couple of items that never seem to work, for me, that you mentioned. Boots of any type are way too much to get in and out of for security – and sometimes security is a couple of times being asked to remove shoes, belts, etc. I stopped wearing big jewelry and belts (when I fly) for that reason. I prefer a ballet flat or even a slip on shoe to make it easy and comfortable.
Also jeans, no matter how stretchy or even a waisted pant with zippers, buttons etc. – while I may pack them, I’m not sitting in them for any long time on a crowded plane in those tiny seats or while I’m getting delayed at the airport. A nice comfy pair of stretchy knit pants with elastic waist or leggings under a dress really does the trick.
I with you on the wrap or coverup of some type, as even though I’m probably the warmest person on the planet most days – some how I’m always the one person under the only existing air conditioning duct.
I always carry some type of large tote, that fits under the seat in front – as I bring stuff to keep me occupied, books, kindle, small handwork, snacks and medications and other stuff that, if I’ve checked baggage, I can’t live without and I also always tote along a tshirt and underware change, just in case that checked bag does get lost, so a least I’ll have clean ones initially.

March 8, 2011 at 1:01 pm

Kristen

(website)

Veteran

I have that Halogen tote in bright blue, and I LOVE it. I use for everyday commuting — fits my laptop and papers perfectly, and looks pretty and polished with no effort.

March 8, 2011 at 1:56 pm

Gracey

(website)

Perfect timing on this post, Angie. I’m going to be doing a little bit of traveling and am not great at deciding what to wear on a plane. One thing I especially struggle with is going from one extreme climate to another. For example, leaving Oregon where it’s still cold and heading to Las Vegas where it’s 20 degrees warmer. I think the casual outfit you presented is perfect for that.

Gracey

March 8, 2011 at 2:38 pm

Inge

What a wonderful new series, can’t wait to see what the next instalment will be about.
I don’t usually travel by air for business, but you’ve made very useful suggestions here, Angie, and I love the tips on how to wear the invididual items in different ways. The leisure travel formula is right up my alley, I love being layered up when flying (and being comfy), so soft jeans or leggings and a not too tight top are definitely part of my travel outfit. Like you, I too always need a warm scarf and I really need those Frye boots now too, not just for travelling, but to wear all the time!-)

Now I am wondering what kind of suitcase you have, is that naughty of me? I’d love to see some stylish yet practical options. Perhaps in another post…?

March 8, 2011 at 2:44 pm

taylor

Veteran

What a great post Angie!!! Thanks for showing us how to travel both for business and pleasure in style and comfort!! So important to do both I think…GREAT flop proof ideas!!!

March 8, 2011 at 4:01 pm

Angie

(website)

Fashion Stylist

Great comments and extra tips!

Laura and Joy, I can’t *ever* remember being warm on a flight. I need to fly with your carriers.

Antje, super rolling laptop bag. Thanks!

Mamark, nice reminder about jewelry, smart phones, collapsible ballet flats and bare shoulders as you pass through security. You’ve also got your traveling outfit routine sorted and I’m impressed.

Inge, we travel with red suitcases so that we can spot them on the baggage claim conveyor belts chop-chop. They are *very* dirty and beaten up. Well used

Kristen, thanks for chiming in about your tote. It is indeed fabulous!

The second outfit idea will work for anyone who travels casually actually. I have a problem with walking barefoot at the US security check points because they make you take your shoes off as you pass through the scanners. That’s one of the reasons I wear socks and boots (and for warmth).

I have no problem with the temperature changes between destinations. If I land in a warm place, I’ll peel off some top layers and I’m fine until we get to the hotel.

Carole, Frye make a lower heeled boot in a similar shape called the Carson.

March 8, 2011 at 4:37 pm

Bevs

This is a great post, and very timely for me as I have to fly to a conference in a couple of weeks! I will definitely make use of these tips. However, as others have pointed out, it is easier to wear shoes on the flight that are easy to slip in and out of, at the security gates. Thanks for the helpful ideas.

March 8, 2011 at 4:48 pm

McKristie

Thank you so very much! I travel weekly for work, and once a month instead of going home I am usually off somewhere for a long vacation weekend – so these posts are great!

I have a version of your outifits that I didn’t realize until just now have become my uniform, I fly out Sundays in the casual outfit and fly home Thursdays in the career outfit – looking forward to the rest of the posts!

March 8, 2011 at 5:28 pm

Sihaya

Veteran

Angie, thank you for this post. Fortunately for me I can travel casual because I usually head to a hotel from the airport before my business meetings. I have to have cover ups as I almost always get cold on the plane and nowadays you can’t even get a blanket on the flight if you’re flying coach. I can’t imagine wearing a skirt on the plane. I almost always wear jeans. On the rare occasions where I have to go straight to work, I wear trousers but don’t like that they and the jackets can get more creased as a result.

March 9, 2011 at 6:30 am

Debora

Veteran

Great post, Angie! I also have a problem with going barefoot through security. During the summer months when I often wear ballet flats, I carry a pair of footies in the outside pocket of my carry-on to slip on when I go through the security line.

I’ll have to look for that Halogen bag and polka dot scarf. Thanks for the flop proof formulas!

March 9, 2011 at 7:10 am

Angie

(website)

Fashion Stylist

I’m glad that this post helped!

It is much more important to me that I have the right footwear for my trip and for the flight than it is to be able to slip my shoes on and off quickly at the security checks. In fact, I’m not worried about that all. You move out of the way to the chairs and tables provided, and it takes two extra secs to put on footwear that does not slip on and off. Plus, you only take your shoes off at US security points. You are not required to do so in other countries, so for me – it’s even less important to wear slip on shoes for air travel!

March 9, 2011 at 9:19 am

Scarlet

Veteran

This was a great post! I will be referring back the next time I am planning a trip.

March 9, 2011 at 2:23 pm

Maya

Veteran

I never travel for business and seldom travel for pleasure, but when I do, I cannot wear jeans or anything binding. I swell up like a marshmallow. Leggings and blousy tunics are my friends.

Footwear is the hardest. Still no ideal solution. Boots and sandals are usually best, even if they’re a security nightmare. I can’t wear slip-ons so it will never be a quick, smooth experience.

March 9, 2011 at 7:37 pm

Inge

Thanks for satisfying my curiosity, Angie! I should have guessed you guys have red suitcases;-) And good point, a bright colour immediately stands out.

March 10, 2011 at 3:48 pm

April

Veteran

I never travel for work but am a frequent train traveler in my personal life. You’ve all hit the high points of wardrobe so I won’t recap, but here is a tip for train travel: do not hang any kind of larger bag on one shoulder as you go down the aisle of a train. If you turn even a little bit, your bag will inadvertently whack the person sitting on the aisle. I must see this happen three or four times on every train trip, and most of the time the whacker doesn’t even realize it happened.

March 13, 2011 at 5:24 pm

Elbe

Great tips! I do travel for business. I made a game out of trying to pack everything into a carry on bag. With the right combo, you can go for 4-5 days. The only drawback is that I feel limited in my choices. If I don’t have my whole wardrobe at my disposal, I feel like people don’t really see who I am. They just see the travel me. The home me is much more interesting!

April 4, 2011 at 12:42 pm

Vicki

(website)

Veteran

With so many wonderful colors offered with the Halogen Seamed Pencil Skirt, is there a “go to” color you would recommend? I know black is basic, but some of these colors look like a nice addition, but I don’t want to make color mistake. Your thoughts, from one blonde to another?

August 29, 2011 at 10:59 am

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Flop Proof Traveling Outfits

Career Wear: Plane to Meeting

Casual Wear: Plane To Hotel

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