What To Wear To Disney World

Here’s a question I get a lot… What should I wear to Disney World?

If you’ve been to Disney, you know it’s all about comfort. You’re walking from morning until night, hopping on and off rides, and you’re trying not to have to lug around too much stuff. How do you look cute, but keep it practical? Here are a few suggestions.


1.  Check the Weather

Weather is important when you’re putting together an outfit. What to wear to Disney World in July is going to be quite different from what to wear to Disney World in February. July is the hottest month with temperatures averaging 28° c ( 82ºF). It’s also the month with the most rain. Jan/Feb are the coldest months in Orlando with temperatures averaging 15-16ºC (59-60ºF).1. Consider the Weather

Continue reading “What To Wear To Disney World”


Comfy Fall Shoes and Booties to Wear in NYC

Hi Deborah,

I LOVE your website! I was wondering if you can give me some ideas for an upcoming trip to NYC. I am traveling with my husband, mother, and teenage daughters this fall, and we will be doing a LOT of walking around – visiting museums, going to the theater, and window shopping. Could you please advise me on what shoes (or short booties) to wear in New York? Thanks a lot!~Carol

Hi Carol,

I’m so glad you ask about shoes because they are the most important item you need to pack.  New York is a walking city, and you will be pounding the pavement for blocks on end. If your feet aren’t comfortable, you will be miserable! Continue reading “Comfy Fall Shoes and Booties to Wear in NYC”


What Shoes To Wear on A Cruise

Dear Deborah,

What shoes should I pack for a Caribbean cruise?  There will be formal nights and casual nights onboard the ship, and I’ll need shoes for land excursions.  I don’t want to pack too many shoes, but I want to make sure I have the right shoes for my outfits and the different activities. What shoes should I wear on my cruise and how many should I bring?  Thanks, Sandra

Hi Sandra,

Knowing what shoes to pack for a cruise can feel overwhelming for sure, but don’t worry because I’m going to break it down for you.  First of all, no matter what shoe you bring, follow these guidelines to get it right.

For a cruise you will want to bring shoes that are:

Summery: It may be freezing where you are right now, but it’s going to be super hot and balmy on your Caribbean cruise. Pack shoes that are light, open, and airy. Nothing heavy or “northern.”

Comfy: Cruises involve a lot of walking.. around the ship (which is typically four football fields long and 16 stories high) and in port shopping and sightseeing. Make sure your shoes have some padding are not stiff. Above all, be sure to work them in at home before you step on board!

Easy to walk in: In addition to being comfy, make sure your shoes are easy to walk in. I’m talking about any high heels you might feel compelled to bring for a formal dinner night. High heels are not the easiest to walk in, period, and on a big ship with varying surfaces ranging from wooden decks to busy narrow carpeted hallways, it’s really awkward. Think about lower heels, or block heels, or wedges.

Versatile: No one wants to lug a suitcase full of shoes onboard. Make sure the shoes you bring go (in terms of color and style), with at a few of your outfits- not just one. 

Fun: You’re on holiday! Please don’t bring anything too serious or business-like. Choose shoes that are more flirty and playful and show off your personality.

Tropical: Warm weather means brighter and lighter colors and even island touches on shoes like rope, cork, and raffia details. You can’t go wrong with a shoe with a tropical feel on a Caribbean cruise.

Trending: A cruise is like a floating party or a floating city. It feels special. Don’t settle for bringing your two-year-old sandals that don’t really look that modern anymore. Treat yourself to something new and hip to look and feel special on this fabulous trip that will give you memories to last a lifetime!

Now let’s break down the four types of shoes you will need

  • comfy walking shoe, casual sandal, casually smart sandal, & sexy shoe (optional)


Cruise Shoes - Shorts


1. Comfortable Walking Shoes

Whether you are getting some morning exercise motoring around the ship or pounding the pavement in an ancient city, you will need some very comfy walking shoes. This doesn’t mean big clunky white jogging shoes with zero styles. There are many sleek, stylish and foot-friendly walking shoes out there.

Some of the most popular types in the last few years have been slip-on sneakers, lace-up statement sneakers, sporty Mary Janes, and canvas or cloth type walking shoes with sporty rope trimmed soles.
Continue reading “What Shoes To Wear on A Cruise”


Super Comfortable Wedges for Walking

Dear Deborah,

I’m getting ready for a trip to Europe and need your help with footwear. I just purchased a pair of running type shoes, ( Ecco  flats),  but I also want to bring some wedges that are comfy, and that will look good with my outfits, particularly my sundresses. What do you suggest? 

Thanks, Cynthia S. – Boston, MA

Dear Cynthia,

You are in luck since I recently came across a new brand of walking shoe.  Fly London is a European brand that is made with comfort and style in mind. Their styles are a little more funky and clunky than I usually show, but they work.

Fly London