For trips with events: think, what do I want to look like at this event? Consider a bunch of options. Pick one. Ok, I know you, you can pick two. But they have to be the entirety of the outfit as you imagine it. Not elements that could cohere. Pick the shoes, bag, jewelry you want for that event.
Then, you gotta do the rest of your packing with a ratio - 3 neutral/flexible items (jeans, good trousers, a button down shirt, a good cardi) to 1 out-there item (for you I imagine sparkles, pleather). You gotta be able to imagine a bunch of ways you can mix the out-there stuff with the useful, reliable, makes you feel comfortable and put together stuff. You need to think about how much is formal work versus just hanging out.
Then you want a pair of boots, a flat, some sneakers, and a fun shoe if you want. I personally just like really good boots and flats. You want a scarf.
Jenn this reminds me of the time I let my 5 year old pack his own bag, which he filled with three pairs of socks and all the plastic dinosaurs he could jam in. :) Ok it sounds corny because it has a name, but, the 5-4-3-2-1 packing system is solid. Even if sometimes it goes more like 64322, or whatever it is a great way to build the base.
So glad you loved Chicago! When you and Kim muse about affordable but cool places to live outside of NYC and LA on EIF, I always think, "If only they spent more time in Chicago - it checks a lot of boxes." It has its problems (gross winter weather, unmatched pay-to-play political corruption, disinvestment in neighborhoods traditionally home to POCs just to name a few), but most of us here love it, warts and all, and are proud to call Chicago home. Please come back and visit us in the summertime when the city really sparkles - you could spend at least a week here exploring our many beautiful neighborhoods!
Hello from Chicago:) Do you remember Garanimals clothing for kids? It was around when we were kids. The idea was each garment had an animal tag, and you could then match that animal (say, a tee with a giraffe tag) with any other garment that had the same tag (pants with a giraffe). I think it was meant to help kids dress themselves. I travel often, and I think about Garanimals when packing! Three outfits that can mix or match, wear one outfit on the plane, and add two extra tops. Extra socks, extra shoes, extra underwear and always one "nicer" option. Just in case you end up at the Union League Club:)
this is a possibility! Though I think it's more not really thinking it out practically and also having an at-home wardrobe built for "imagination" and "discovery"
😂 There is no suitcase that can contain “imagination” and “discovery.” Creatives are just fucked when asked to perform sensibly in this world. (Speaking as one myself 🩷)
This makes sense! When packing, I try to visualize the specific outfits I will wear and then I add some fun pieces just in case. But it's partially why I don't love to travel...I feel like I am leaving so much of my self at home!
I just literally create outfits, including underwear, bras, jewelry, and socks, one for each day I will be gone, and neatly stack them on my bed. Then I take out a bra or two, depending on the number of days, add in a couple of extra pairs of underwear (because I'm paranoid), and one extra pair of socks. All of that goes in my suitcase, plus sleeping things, an extra sweater (because AC always makes me too cold), and a bathing suit if there is any chance at all I might need one. Also, all the standard toiletries.
Can't help with figuring out events because I don't get invited to fancy things. But a basic black dress and some matching shoes seem like they could always work?
I don't quite get down to the undergarments level, but I do figure out combinations for each day of tops, bottoms, and shoes. I also try to pick skirts or pants that can go with more than one top because I'm the queen of packing light and try to minimize wherever I can. Plus one to extra underwear too! And a non-bulky cardigan for cold hotel rooms. I'm also fanatic about only packing one extra pair of shoes.
My packing problem is that I always forget one important item, like I'll bring a toothbrush but forget the toothpaste, or I'll pack the perfect balance of outfits but forget to pack something to sleep in. It's never anything too serious, but always an inconvenience.
Oh girl... As someone who flies all over the country regularly I still find packing paralyzing. I want to dress comfortably and attempt some level of sophistication (thanks to Kim, Andrea, and a small troupe of fellow fashion-focused substackers, I feel I'm getting close), but certain clothing items like a blazer would get crunched in my suitcase. So either I leave that item at home or I wear it on the plane. If I'm gone for four days, I usually wear a version of the same thing flying there and back, then I pack two main work outfits, pjs, a set of workout clothes, and a couple of pairs of shoes (all in shoes bags bc ewww), plus toiletries, undergarments, and socks. I always figure out what I am going to wear on the plane first. I also wear compression socks which cuts down on the cute shoes and bare ankles but I would rather not have additional health issues arise from my vanity. Here is where I start packing my roll-aboard: pjs, slippers, and workout clothes first, then the main outfits which is where I have the most trouble but laying them out beforehand with the shoes and socks helps a lot, then stuff the shoes with socks. I usually bring too many pairs of socks but once I got caught in a torrential downpour and was glad I had that extra pair. Same with underwear- better to have that extra pair and not need it-plus they're small and light so that extra pair isn't going to be an issue. My toiletry bag is always overstuffed. I can't figure out why but I think it's due to separate day and night regimens. I also carry a cotton garment bag for dirty clothes which I can chuck into the washing machine when I get home. That way I avoid using the plastic laundry bag in the hotel closet. Lastly, I throw in my hair tools. Everything fits miraculously well, which allows me to bring home things I bought.
The bigger challenge is when I am going on a longer trip especially if it's for a conference where I will be seeing the same people over several days. When I am traveling for meetings at different places I will recycle outfits- maybe bringing an extra shirt or two in case of stink or stains. In my larger tote which doubles as my purse, I will include antibac wipes for the hotel and plane (always at the ready when I am on the jet bridge), Tide pen, febreze spray, and other travel sized odds and ends that help.
I worked with a great stylist, Annie Brumbaugh, sadly no longer living. She taught me basic principles. You know you’re scattered. Why not build a capsule wardrobe that leaves you ZERO decisions? Takes discipline but solves the What To Pack What To Wear problem. Update 2x yr max. Unless you really love the chaos! Which is fine!
Holy FUCK!....are you KIDDING me with this? Today? I am currently staring at a god damn MESS of clothes that are somehow supposed to fit into one small suitcase. However, that isn't the truly sad part of this. I am going from NYC where my husband and daughter live full time to...MY place upstate where I haven't been for 3 weeks (RIP democracy.) And, yet....AND FUCKING YET! I....I have no idea how to cull through the mess I've made to figure out what to leave here and what to take back to WHERE I MOSTLY LIVE! In case you can't tell, this is generally the extent of my travel -- the 100 miles between here and there. This is ridiculous and yet...I don't know. I'm still starting at that pile. Good luck, Jenn....I might not have any confidence in myself here but I have COMPLETE confidence in you! XOX
Laughing so hard at three turtlenecks and no bra!!! I do the same thing someone else mentioned: I visualize outfits, down to the socks and underwear, in my head, then write all the items down on a scrap of paper, and pack. But I'm still sometimes unhappy/unprepared.
I'm currently packing for a 10 day vacation in cold rainy northern Europe in just a carry-on. I'm keeping it very basic - two sweaters, 5 tees/undershirts, 2 pairs of jeans and one pair of soft pants. Boots and sneakers. And underclothes for every day. My outfits won't be inspiring but they'll be warm and serviceable. I'll have room to add a few new pieces as I travel.
I'm in finance so I guess I have it easy with a 'uniform' of sorts that I tend to wear over and over. I save the more creative outfits for when I'm on vacation and can bring a larger bag, or when I'm at home and attending events and have the benefit of my full closet arsenal. Trust me I love clothes and would love to have more options but I don't look at business travel as an opportunity to mix things up. While our fields are different you can take the same approach: stick with a few quality items that travel well and those are those are the ones you bring on your trips, over and over again.
This is exactly how I think about work travel. I used to try to creative ‘wow’ outfits every time I travelled and it was so stressful. I now have very nice, but essentially boring outfits which I always take with me with variations for weather/temperature. I try to get a blow dry before I go or once I’m there to feel good about how I look - with swishy hair I don’t care how boring my outfit is.
Lately I've packed one subtle but not boring (oxymoron?) thing for my business outfits: a sheer gray fine mesh shirt that I wear under a vest with trousers. I don't know if anyone else can tell it's sheer or if it just looks like a grey long sleeve tshirt, but it makes me happy. If it's too hot to wear a vest, I have a couple of re-made mens' shirts with the buttons moved, so they're just different enough to content me.
I have no advice because I just wear the same usually flower dresses for almost all events. This skirt looks amazing! Love the leopard print and black fringe.
You think you can't pack because you dress beautifully creative. I can pack but because I dress boring (think quiet lux on a budget and all neutrals and 501 Levis). I think I could pack blindfolded and all the clothes would still work!
I think you need to some body doubling, either FaceTime a friend while packing or have someone come over to help or have someone in your room doing their own work while you’re packing or use taskmate.com to be paired up with a stranger who is also getting something done whenever they are. What you discovered in your suitcase sounds like a panicked person packed it while feeling ungrounded and alone. It’s OK to need company for a task like that when you’re building up your skill
set (or maybe forever if you like it) I start a few days before by packing the things I will be stressed out to forget. For me that’s meds, toiletries, PJs and appropriate outerwear. Put those in packing cubes and leave slightly unzipped so you can see what is in there if you lose track. This will declutter your packing area. There are also downloadable packing lists on Etsy or you could make your own so you can check things. Sounds as if you get particular focused on full outfits so I’ll echo what other people said about making a pile for each of those and it can go into its own packing cube.
Also, agree with others who recommend bringing an empty laundry pouch in the suitcase. Mine is bright orange, this easy to see it’s not a packing cube and just put stuff to be laundered in there so your pile of clothes to wear gets smaller and not jumbled up with dirty clothes
I am a big organized nerd so I have a packing list in a google spreadsheet, and every time I’m going somewhere I copy it and adjust for location, weather and so on. So I remember things like meds and hair products. And yes to making an outfit for every day, plus a few extra things. Shoes are always the biggest challenge though.
Packing is one of my few skills. I got you.
For trips with events: think, what do I want to look like at this event? Consider a bunch of options. Pick one. Ok, I know you, you can pick two. But they have to be the entirety of the outfit as you imagine it. Not elements that could cohere. Pick the shoes, bag, jewelry you want for that event.
Then, you gotta do the rest of your packing with a ratio - 3 neutral/flexible items (jeans, good trousers, a button down shirt, a good cardi) to 1 out-there item (for you I imagine sparkles, pleather). You gotta be able to imagine a bunch of ways you can mix the out-there stuff with the useful, reliable, makes you feel comfortable and put together stuff. You need to think about how much is formal work versus just hanging out.
Then you want a pair of boots, a flat, some sneakers, and a fun shoe if you want. I personally just like really good boots and flats. You want a scarf.
I need to print this out and stick it to my forehead.
This is excellent advice!
Jenn this reminds me of the time I let my 5 year old pack his own bag, which he filled with three pairs of socks and all the plastic dinosaurs he could jam in. :) Ok it sounds corny because it has a name, but, the 5-4-3-2-1 packing system is solid. Even if sometimes it goes more like 64322, or whatever it is a great way to build the base.
LOOKING UP THIS WIZARD MATH IMMEDIATELY
So glad you loved Chicago! When you and Kim muse about affordable but cool places to live outside of NYC and LA on EIF, I always think, "If only they spent more time in Chicago - it checks a lot of boxes." It has its problems (gross winter weather, unmatched pay-to-play political corruption, disinvestment in neighborhoods traditionally home to POCs just to name a few), but most of us here love it, warts and all, and are proud to call Chicago home. Please come back and visit us in the summertime when the city really sparkles - you could spend at least a week here exploring our many beautiful neighborhoods!
Hello from Chicago:) Do you remember Garanimals clothing for kids? It was around when we were kids. The idea was each garment had an animal tag, and you could then match that animal (say, a tee with a giraffe tag) with any other garment that had the same tag (pants with a giraffe). I think it was meant to help kids dress themselves. I travel often, and I think about Garanimals when packing! Three outfits that can mix or match, wear one outfit on the plane, and add two extra tops. Extra socks, extra shoes, extra underwear and always one "nicer" option. Just in case you end up at the Union League Club:)
I wonder if you pack poorly on purpose (if subconsciously) because then you get to buy something new and shiny and exciting on the trip...!
this is a possibility! Though I think it's more not really thinking it out practically and also having an at-home wardrobe built for "imagination" and "discovery"
😂 There is no suitcase that can contain “imagination” and “discovery.” Creatives are just fucked when asked to perform sensibly in this world. (Speaking as one myself 🩷)
haha yes
exactly
This makes sense! When packing, I try to visualize the specific outfits I will wear and then I add some fun pieces just in case. But it's partially why I don't love to travel...I feel like I am leaving so much of my self at home!
I just literally create outfits, including underwear, bras, jewelry, and socks, one for each day I will be gone, and neatly stack them on my bed. Then I take out a bra or two, depending on the number of days, add in a couple of extra pairs of underwear (because I'm paranoid), and one extra pair of socks. All of that goes in my suitcase, plus sleeping things, an extra sweater (because AC always makes me too cold), and a bathing suit if there is any chance at all I might need one. Also, all the standard toiletries.
Can't help with figuring out events because I don't get invited to fancy things. But a basic black dress and some matching shoes seem like they could always work?
I don't quite get down to the undergarments level, but I do figure out combinations for each day of tops, bottoms, and shoes. I also try to pick skirts or pants that can go with more than one top because I'm the queen of packing light and try to minimize wherever I can. Plus one to extra underwear too! And a non-bulky cardigan for cold hotel rooms. I'm also fanatic about only packing one extra pair of shoes.
My packing problem is that I always forget one important item, like I'll bring a toothbrush but forget the toothpaste, or I'll pack the perfect balance of outfits but forget to pack something to sleep in. It's never anything too serious, but always an inconvenience.
PS: The Chicago riverboat architecture tour is THE BEST. An actual must-do.
Oh girl... As someone who flies all over the country regularly I still find packing paralyzing. I want to dress comfortably and attempt some level of sophistication (thanks to Kim, Andrea, and a small troupe of fellow fashion-focused substackers, I feel I'm getting close), but certain clothing items like a blazer would get crunched in my suitcase. So either I leave that item at home or I wear it on the plane. If I'm gone for four days, I usually wear a version of the same thing flying there and back, then I pack two main work outfits, pjs, a set of workout clothes, and a couple of pairs of shoes (all in shoes bags bc ewww), plus toiletries, undergarments, and socks. I always figure out what I am going to wear on the plane first. I also wear compression socks which cuts down on the cute shoes and bare ankles but I would rather not have additional health issues arise from my vanity. Here is where I start packing my roll-aboard: pjs, slippers, and workout clothes first, then the main outfits which is where I have the most trouble but laying them out beforehand with the shoes and socks helps a lot, then stuff the shoes with socks. I usually bring too many pairs of socks but once I got caught in a torrential downpour and was glad I had that extra pair. Same with underwear- better to have that extra pair and not need it-plus they're small and light so that extra pair isn't going to be an issue. My toiletry bag is always overstuffed. I can't figure out why but I think it's due to separate day and night regimens. I also carry a cotton garment bag for dirty clothes which I can chuck into the washing machine when I get home. That way I avoid using the plastic laundry bag in the hotel closet. Lastly, I throw in my hair tools. Everything fits miraculously well, which allows me to bring home things I bought.
The bigger challenge is when I am going on a longer trip especially if it's for a conference where I will be seeing the same people over several days. When I am traveling for meetings at different places I will recycle outfits- maybe bringing an extra shirt or two in case of stink or stains. In my larger tote which doubles as my purse, I will include antibac wipes for the hotel and plane (always at the ready when I am on the jet bridge), Tide pen, febreze spray, and other travel sized odds and ends that help.
I worked with a great stylist, Annie Brumbaugh, sadly no longer living. She taught me basic principles. You know you’re scattered. Why not build a capsule wardrobe that leaves you ZERO decisions? Takes discipline but solves the What To Pack What To Wear problem. Update 2x yr max. Unless you really love the chaos! Which is fine!
I actually do want/need a capsule wardrobe (though I fear I need an "excitement" wardrobe to hide behind more!)
Holy FUCK!....are you KIDDING me with this? Today? I am currently staring at a god damn MESS of clothes that are somehow supposed to fit into one small suitcase. However, that isn't the truly sad part of this. I am going from NYC where my husband and daughter live full time to...MY place upstate where I haven't been for 3 weeks (RIP democracy.) And, yet....AND FUCKING YET! I....I have no idea how to cull through the mess I've made to figure out what to leave here and what to take back to WHERE I MOSTLY LIVE! In case you can't tell, this is generally the extent of my travel -- the 100 miles between here and there. This is ridiculous and yet...I don't know. I'm still starting at that pile. Good luck, Jenn....I might not have any confidence in myself here but I have COMPLETE confidence in you! XOX
Laughing so hard at three turtlenecks and no bra!!! I do the same thing someone else mentioned: I visualize outfits, down to the socks and underwear, in my head, then write all the items down on a scrap of paper, and pack. But I'm still sometimes unhappy/unprepared.
I'm currently packing for a 10 day vacation in cold rainy northern Europe in just a carry-on. I'm keeping it very basic - two sweaters, 5 tees/undershirts, 2 pairs of jeans and one pair of soft pants. Boots and sneakers. And underclothes for every day. My outfits won't be inspiring but they'll be warm and serviceable. I'll have room to add a few new pieces as I travel.
I'm in finance so I guess I have it easy with a 'uniform' of sorts that I tend to wear over and over. I save the more creative outfits for when I'm on vacation and can bring a larger bag, or when I'm at home and attending events and have the benefit of my full closet arsenal. Trust me I love clothes and would love to have more options but I don't look at business travel as an opportunity to mix things up. While our fields are different you can take the same approach: stick with a few quality items that travel well and those are those are the ones you bring on your trips, over and over again.
This is exactly how I think about work travel. I used to try to creative ‘wow’ outfits every time I travelled and it was so stressful. I now have very nice, but essentially boring outfits which I always take with me with variations for weather/temperature. I try to get a blow dry before I go or once I’m there to feel good about how I look - with swishy hair I don’t care how boring my outfit is.
Lately I've packed one subtle but not boring (oxymoron?) thing for my business outfits: a sheer gray fine mesh shirt that I wear under a vest with trousers. I don't know if anyone else can tell it's sheer or if it just looks like a grey long sleeve tshirt, but it makes me happy. If it's too hot to wear a vest, I have a couple of re-made mens' shirts with the buttons moved, so they're just different enough to content me.
I have no advice because I just wear the same usually flower dresses for almost all events. This skirt looks amazing! Love the leopard print and black fringe.
You think you can't pack because you dress beautifully creative. I can pack but because I dress boring (think quiet lux on a budget and all neutrals and 501 Levis). I think I could pack blindfolded and all the clothes would still work!
thank you for this but also your style sounds like a dream to me!
I think you need to some body doubling, either FaceTime a friend while packing or have someone come over to help or have someone in your room doing their own work while you’re packing or use taskmate.com to be paired up with a stranger who is also getting something done whenever they are. What you discovered in your suitcase sounds like a panicked person packed it while feeling ungrounded and alone. It’s OK to need company for a task like that when you’re building up your skill
set (or maybe forever if you like it) I start a few days before by packing the things I will be stressed out to forget. For me that’s meds, toiletries, PJs and appropriate outerwear. Put those in packing cubes and leave slightly unzipped so you can see what is in there if you lose track. This will declutter your packing area. There are also downloadable packing lists on Etsy or you could make your own so you can check things. Sounds as if you get particular focused on full outfits so I’ll echo what other people said about making a pile for each of those and it can go into its own packing cube.
Also, agree with others who recommend bringing an empty laundry pouch in the suitcase. Mine is bright orange, this easy to see it’s not a packing cube and just put stuff to be laundered in there so your pile of clothes to wear gets smaller and not jumbled up with dirty clothes
I am a big organized nerd so I have a packing list in a google spreadsheet, and every time I’m going somewhere I copy it and adjust for location, weather and so on. So I remember things like meds and hair products. And yes to making an outfit for every day, plus a few extra things. Shoes are always the biggest challenge though.