Reliable Chic City Vacation Style: Exploring the Sights

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How to pack for a city vacation

Reliable Chic City Vacation Style: Exploring the Sights

When you go on your city vacation, you want reliable and chic outfits no matter where you decide to visit. For our city vacation style, I’m showing ideas for exploring the town on foot. This would include those fun activities like seeing museums, shopping and of course lunch thrown in for sustenance.

Quote of the day: “The man who views the world at fifty the same as he did at twenty has wasted thirty years of his life.” Muhammad Ali

Our summer series about vacations has included the beach trip, the rustic getaway and now the city vacation. Charlotte showcased an idea of what to wear to an evening show (or dinner). And Lesley talks about the idea of a bus tour.
Personally, my husband and I used to visit NYC every Labor Day weekend for about 10 years, so I have it down pat what works for me. As for you, it’s good to analyze your agenda and what makes you comfortable!!
The most important factor?? It’s vacation so have fun!!

Other posts about what to pack and wear on a trip
What to Pack for the Holidays with Paradise Baggage
Breaking Down the Anatomy of a Perfect Airplane Outfit
My NYC Packing List and What I Did Right and Wrong

Staying cool on a summer city vacation

Dress: Adrienne Vittadini -thriftted ~~ Top: Madewell ~~ Shoes: Walking Cradles c/o~~ Bracelet: Audra Style c/o~~ Earrings: Audra Style c/o~~ Purse: Charming Charlies-thrifted

City Vacation Style for Exploring the Sights

Depending which city you are going to visit and what time of year, a dress can certainly be more versatile than you think. Most city vacations involve some wonderful events where a dress can be the perfect clothing item.

I’ve shown many times how a dress can be worn as a skirt, a top, as well as a dress. Once you get in the habit of thinking of your dress in multiple ways, then it becomes so versatile.

Insider tip: Many times I wear a tee or camisole under the dress so the dress itself doesn’t have to be washed between wearings. Of course if you spill on the outside, then that’s a different story, LOL!

For my outfit exploring the town this day, I wore a thrifted dress that I could easily take from day to night with a couple of quick changes. Granted if you didn’t have time to stop back at your hotel, I could take off the chambray top and go out in the dress.

Blouse over a dress


I always take many accessories on a city vacation. They are small and easy to put in my luggage, and can change up the look of any outfit. I’ve even learned that it’s not hard to throw another purse in my suitcase as opposed to carrying the tote I use for my plane trip.
These colorful Audra Style earrings (and bracelets) are perfect because there are so many colors in them that they go with everything.

Insider tip: If you have a cuff bracelet that is too big, put a piece of hat tape in it. I show how in this short video and you can buy hat tape on Amazon.

For a day exploring, I do prefer a purse that is hands-free. While I love my belt bags, I grabbed this mint-colored crossbody purse instead because I can use it for our dressier events also.
I recommend keeping your purse as small as possible. When you’re walking around all day, you don’t need to carry any unnecessary extra weight.

The other “accessory” I happen to be sporting is sunglasses. Really, these are my regular glasses that transition from clear to tinted. It’s certainly more convenient to have one pair that changes than to try to switch them out and carry many glasses around on a trip.
I admit that the transitions don’t get as dark as my other sunglasses, but for a city vacation like this, it may not be as necessary as say, for a beach vacation.

Other online glasses posts
How to Pick the Right Glasses Frame for Your Face and Tips for Online Glasses
There are Many Options for Buying your Eye Prescription Online Glasses

City vacation outfit for exploring

Chambray Shirt

I always take some kind of covering wherever we go. It’s great for sun protection or in case the stores are chilly. If it’s too hot, then I can always take it off and tie it around my purse.
Since denim goes with everything, I thought a chambray shirt was a good idea. Just the fact that it buttons up the front allows me to style it a couple of different ways.

Sneakers for walking on vacation

Walking Shoes

The one thing that is paramount when you are walking around during a city vacation and exploring is comfortable shoes. And I don’t mean shoes that feel okay while you’re sitting around. These need to have support and feel good (and looking cute is the chic part of the title for this post).

Comfortable shoes have been on my radar more and more lately. It’s one item that I am willing to spend more money on since the functionality is so important.

This colorful pair is the Orleans by Walking Cradles. I have 6 different prints in this style of shoe which tells you how great they fit. While these are sneakers, I think they look almost like a loafer and therefore work all day long. In fact, one of my friends and I showcased how they can be styled from fitness to dress up.

Other comfy shoe posts
Comparing Comfortable Everyday Shoes with 4 Different Companies
A Spotlight on Stylish Walking Shoes with Tiosebon for 3 Different Decades of Women
Introducing and Comparing 3 Versions of Aetrex Footwear

Out exploring for a summer city vacation
City vacation style

Photo credit: Rob Filogomo

My Goal

Thank you for visiting my space on the internet. I like to showcase how it’s never too late to look great for women of any age, size or working with any budget.
I feel I’m here to help move beyond the fashion rules of yesterday and evolve. Style and clothes are made to give you joy. Not cause us stress because we are worried about what other’s think.

My hope is that you get ideas and inspirations from Charlotte, Lesley and myself. It’s not about copying what we wear, but about using what you already have and updating items along the way.
Most of all it’s getting us to think differently and dare I say, have fun?


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