What kind of bag I bring depends on where I'm going. I tend to bring a big handbag for the flight. I use my Mulberry Picadilly for that. It's heavy, but fits a lot, and buy that I mean, if I buy anything at the airport I can put it right in and don't have to carry any extra bags. So don't overstuff it at home
For sightsing, a smaller handbag with shoulderstrap that I can close. I don't want to worry about pickpockets but it still has to hold a small wallet, waterbottle, guidebook etc. This bag has to work both for sightsing and look good when I go out at night. I only bring one handbag!
As for shoes. Were what ever you are comfy with and bring two. Switch each day. Your shoes and feet will thank you. One of the pair should be something you also can use at dinner.
In terms of handbags, not luggage, I take a large leather tote on the plane, either Longchamp red leather tote or Dolce & Gabbana camel leather shoulder bag. I'll have a small clutch in that bag as well as all my inflight carry on needs etc.
I'll generally pack a longchamp le pliage in my suitcase as well, just in case...
Shoes in the airport? I usually wear either a pair of ballet flats or a pair of Tods loafers on the plane.
I agree with mediana it completly depends on where Im going. On the plane I always take my laptop so I use my laptop case as a handbag as well. I usually dont take my expensive bags on vaca. I just dont feel comfortable. Im weird I know! I end up taking a trusty and cute marc by marc jacobs.
For the plane I always wear flip flops and for sightseeing a cute pair of ballet flats. Comfy and cute
^No you'r not weird. I'm just the same I don't bring my more expensive bags with me. I have a small handbag from Bally I use when I travel and only then. Don't know why. I also have a wallet from Miu Miu that only comes out then
As much as it just breaks my heart to NOT take an expensive bag with me while travelling, I just go ahead and take one of my cheaper bags with me, especially when we travel on a cruise. It just works out much better that I can stuff it with purchases, sling it around, and not care if it gets smudged. I would hate if anything happened to any of my really great bags on vacation. So, I usually end up taking a larger generic tote.
i also tend to travel with less expensive bags. i usually use a large black leather tote. i need a really large bag b/c i tend to throw EVERYTHING in there....sunglasses, cardigan, travel guides, camera, wallet, etc...
i usually wear flipflops when sightseeing...and i always carry an extra pair in my bag b/c i am so paranoid that the current pair that i'm wearing will break (it has happened before...i had to sit down and wait for my bf to run around and buy me a new pair)
I don't take my more expensive bags either. Usually one of my cheaper Coach bags. One bag I have been taking as of late is my large Timbuk2 Messenger bag. It is large enough to hold my toiletries, trip info and some camera gear.
Also I can fit one of my small Coach purses in it as well.
The last few trips I've taken I brought my Jimmy Choo Riki bag. I just bring one bag and my laptop in its case. I would travel in flats due to so much walking and maybe bring one other pair. I don't usually travel with heels unless I might have somewhere specific to wear them. I just usually do too much walking.
I use a black slouchy Furla bag that has a removable shoulder strap so I can carry it cross-body, my Hermès Evelyne and my Louis Vuitton Eva. When I'm carrying the Evelyne I clip the Eva onto one of the metal thingys that hold the strap so my wallet and phone are safe inside the Evelyne (since it's an open-top bag).
Depending on the duration of the trip, I either bring my Bal weekender or Longchamp pliage on the plane. In addition, I usually bring one smaller bag for sightseeing and then maybe a clutch or something similar for dinner.
This summer, I'm bringing my Bal weekender as a carry-on, with my Dior Gaucho for sightseeing (that thing can keep a whole lot of things despite looking small and nothing more significant than a shoulder bag!) and a Bal First/Hermes Mini Plume for dinners.
The smaller bags are always with me on the plane; never checked-in.
For my daytime bag I just bought a large black Kate Spade bag. It's got a ton of pockets for throwing everything in & big enough to hold a cardigan, an umbrella, guide books, my camera & a bottle of water.
I figured it was very nondescript looking-no flashy logos, but still tasteful enough for if I want to go somewhere nicer. It's black so it'll go with everything I'll wear & since it's not leather, I don't have to worry about rainy days.