Packing for a wedding
 

Starting a new thread for this so that I can follow up with the actual results. This one is going to put my "carry on only" vow to the test not only due to the required number of shoes (I'm trying to hold fast at 3 pairs) but also due to the two male peacocks that I'll be flying with. If we absolutely have to go with more than 1 small roller & 1 personal item each then I'm planning on what's less important that can go in a communal checked bag. I also plan on test packing this weekend. And packing cubes :). But the true trial is going to be what fits where and how it all fits together.
My dress is a simple St John sheath with jacket. This should travel well.
Ah also to note, I'm in NY and the wedding is in FL so we're looking at 2 drastic differences in climate. This shouldn't be too daunting as I'll just travel in the heavier clothing.
I appreciate any suggestions and tips from those of you that have done it.

I layer up for the trip to airport - we park in a commercial lot with bus transport to airport, so I don't usually have to stand outside for very long. Sometimes on the return. But for me - a scarf, beanie & gloves can sub in for a heavy coat for 15 minutes and then I don't have to worry about that. For shoes - maybe a pair of flats (I don't like to fly in boots) that I can wear with socks and then take the socks off upon arrival if needed.

Will you be able to reuse the sheath and/or jacket for any other wedding events? If not, can you bring pieces that could be mixed & matched? Conversely, a couple of knit dresses (or thin fabric you could steam upon arrival but packs small) would probably fit nicely for dinner the night before a wedding, brunch the day after - not sure how much you need. Otherwise, I'd bring a pair of light pants (EF crepe or a nice thin cotton ankle pant) with a couple tees and a cardigan and scarf.

How many days is this trip? And how many outfits do you need to have for the wedding--is it just the ceremony/reception on one day, or are there ancillary events like a rehearsal dinner and/or brunch?

The beauty part of this is that the wedding is in Florida. It's warm, and you only need clothes that are light and not bulky. You can wear the same pair of pants and sweater on the trip coming down and the trip going back--just wear a light t-shirt under the sweater and swap out a clean one for the return trip. Wear your coat onto the plane and stuff it on top of your bag in the overhead.

You only need the shoes you're wearing to the wedding plus one other pair of light shoes, *maybe* a pair of flip-flops, but no more. If it were me I'd just wear a light pair of versatile shoes onto the plane from NY and just structure the other non-wedding outfits to utilize them (unless you can re-use the wedding shoes for other events).

I used to do multi-week, multi-climate work trips using just a 20" carry-on. It's not that hard once you learn how to do it--pack mix-and-match clothing, and keep all outfits that require nice shoes in the same color family so that you can wear the same shoes with each one. Also, be unfussy about your toiletries so that you don't have to bring a gargantuan wash bag.

Thank you both! We're gone for 5 days, I've padded travel times a bit to allow for winter delays. There's the wedding itself, brunch the following morning and we're spending a day at Discovery Cove (so I'll need my Keens).

I'll need a jacket but was planning on a lighter one with a nice merino cardigan underneath. The jacket can double as a blanket over my legs on the plane and I'll have the cardigan in case I need it in FL.

Love this idea! Yes, I had planned on a loose knit dress for brunch but the EF route might be a better way to go.

The heels are going to be a one trick pony, unfortunately, and I will need my keens, which will take the packing space reserved for flip flops, but I had planned to fly in my pair of lightweight, knit flats that can double as slippers. These ride along in my carry on anyway so if weather in NY is iffy and I need something sturdier for getting to and from the airport in NY I'll still have my flats. And those flats can walk me to brunch and then out and about regardless if I'm wearing a dress or trousers.

I'm still learning but have gotten so much better about mix & match, packing cubes and carry on only. My toiletry bag is pretty much bullet proof by now but it's still so easy to fall back into the "let me grab this just in case" mindset.

Following up on my trip.
Thank you compression packing cubes! While I did have to tuck a few items into my husband's 1 qt, clear plastic "toiletry bag" I managed to fit everything into my Monos wheeled carry on and personal item (Lo & Sons OG).
Heels with socks tucked into them to keep their shape. Heels were in their bags and then wrapped in my sleep pants & tank to protect them. Heated travel rollers. Small satin evening bag. 2 pairs of stockings (just in case). Packing cube with dress and 2 short jackets (I'm so glad I packed a lighter weight one at a moment of weakness because my original choice would have been too heavy). Packing cube with slip and dainties. Packing cube with tank, cardigan, trousers, work shirt and shorts. Keens packed in a bag for laundry. Packable travel duffle just in case. Large silk scarf. Assorted jewelry. Swimwear pieced tucked in to fill any gaps. Even a lint brush. I flew in jeans, sneakers, long sleeved cotton T and cashmere hoodie with my trenchcoat and umbrella tucked into my OG.. No regrets, no "wish I had brought" s.
Granted my color theme is basic black so everything coordinated.
This was my first trip with the Monos. It's slightly larger than my usual Tumi wheeled carry on and very easy to maneuver. The packing cubes are designed specifically to fit this bag but I use them in any of my bags. Still I was able to fit everything together like puzzle pieces and get everything that I needed into the bag.

Very impressive! Did you happen to take a hat? I'm doing something similar and need a "garden party" type hat that would also work at the beach. I usually take my trusty Tilley when I travel, but it doesn't work for these outdoor party situations!

No hat but I've done a straw hat before for a Bahamas trip. Basically filled the inside of the hat with rolled up items (in that instance it was a slip and tank dress), laid it flat against the back of the suitcase and padded out around the stuffed crown with rolled up T shirts, etc, until everything was firmly packed in place. A hat is a big ask when space is as a premium.
There's part of me that would love the idea of travelling with a separate hat box. Maybe if I had a valet to carry my steamer trunk as well...
Good luck!

Since this is essentially a "carry on" only thread, I have a slightly related question. Would you travel with a friend who checks luggage, even for 3-4 day trips? Do you find a different travel style between your "carry on" and "checked bags" friends? It seems that the travelling we do with friends that check bags is quite different in agenda and style than that with carry-on friends; am I crazy?

I would try to coordinate if possible. Easier to negotiate with my friends - for work, I definitely want to make sure I'm aligned with anyone I have to travel with. I don't mind waiting for checked baggage but I don't want anyone to have to wait for me. That said, for international work trips and trips with friends, I'm often packing liquor or box wine, so I definitely check ;-)