What To Wear to New York City

This past weekend, my husband and I traveled to New York City to do some touring and exploring with his family.

For me, as soon as a trip or vacation is booked, two vital aspects of travel revolve around my mind constantly until departure: what to do and what to wear at the destination. Our extended weekend itinerary was pretty much set, thanks to my mother-in-law’s love to travel and plan, so that left me with one major task: plan my outfits.

How to dress to tour New York City is an inquiry that, in itself, cannot be answered simply; it raises other questions such as, “how do I dress comfortably and stylishly at the same time?” I didn’t want my clothing choices to identify me in the crowds as a tourist, but walking upwards of 10 miles a day would just not be feasible in most of the shoes in my wardrobe. Since we had a lot packed into our schedule each day, I needed to look appropriate and respectable at places like the Metropolitan Museum of Art or nice restaurants for dinner, but I didn’t want to stand out as being overdressed while walking home through Central Park or Times Square. The forecasted weather was HOT, and sitting in a muggy subway and trudging down people-packed streets in the glaring sun also posed another topic of concern: how to dress comfortably, stylishly, and modestly while remaining cool and composed?

Here are two outfits I wore to New York City, and a few tips and ideas to put together your own perfect travel wardrobe!

Outfit One:


  1. H&M Women’s Jersey Dress with Pockets. Simple, casual, and modest, this dress was perfect for walking down the street, but respectable enough for a nice restaurant and our tour guide at The Met. It was surprisingly thin, which kept me cool during our long day in the sun.
  2. This Anthropologie Red Pendant Drop Necklace added nice color to my mostly monochromatic dress; it made the outfit feel polished and “put together”, while not being too fancy or over-the-top.
  3. BORN Danna Sandals in red. Speaking as someone who is always on her feet, this is a great brand of sandals thanks to their supportive soles. They are more hardy as well, so they hold up nicely to the wear-and-tear your will experience from city traversing. I was able to walk in this cute pair all day without any pain!
  4. Travel Bag. When traveling, choosing the right purse can be a big decision. This one has a lot of secure zippered pockets and plenty of room; I stashed my wallet, camera, cell phone, two phone chargers, sunglasses, a water bottle, some make-up, helpful travel documents, and a sweater inside with ease. Perhaps the best feature of this bag is the adjustable cross-body strap because, after a few hours of walking, who really wants to lug around a purse?

Outfit Two:


  1. Target Printed Ankle Pant. I fell in love with this pair of pants as soon as I laid my eyes on them. Fashionable yet functional, I felt able to remain comfortable and classy without sacrificing style.
  2. Gap Knit Tee Shirt in Black. The crazy pattern on the bottom of my outfit just begged for a sweet, simple accent on top, so I went with my trusty Gap tee. Airy and thin, I was super comfortable for our day of exploring.
  3. These Aerosoles Chlothesline Gladiator Sandals are another favorite of mine for comfy, cute walking. I really was drawn to the fact that they aren’t bulky or overly padded, but the flexible sole and memory foam footbed makes you feel like you’re walking on clouds.
  4. Kate Spade Park Floral Mini Pendant and 5. Rhinestone Bangle from Express were the finishing touches for this ensemble! The gold added just a bit of color and warmth to an otherwise colorless outfit, and the cubic zirconias brought the perfect amount of sparkle!

Dress Yourself!

Some things to keep in mind if you are a first-time New Yorker or just looking for ways to refine your travel style:

  • Be careful to watch the shape and length of a dress or skirt; a loose A-line will give a bit of movement with the wind (and all the taxis and cars whizzing past the sidewalk), and taking the subway requires climbing flights of stairs. If it’s too short you might find yourself worrying about holding your dress down all day rather than enjoying the trip!
  • If the weather is forecasted to be “iffy”, or you are easily chilled, dress in layers! Sweaters, casual scarves, and leg warmers are cute and serve a purpose! Plus, they are usually small enough to stash away in your purse or tie around your waist if you do begin to warm up!
  • If you are worried about not being dressed up enough, swap out your shorts for some fitted capris. Pants have a more respectable look than shorts do, and you don’t have to worry about seeming too casual at a nice restaurant or boutique.
  • You can always spot a tourist because they will be wearing inappropriate footwear; experienced New Yorkers know that you don’t have to sacrifice style for comfort, or vice versa. Don’t wear your highest heels, but don’t pull out the tennis shoes (unless you are going for a run). Look for shoes that have thicker, more supportive soles, and soft, stretchy straps. Sandals, modest wedges, and casual sneakers like Converse are all good ideas to start with. It always helps to break in your shoes before you wear them as well, just to make sure they don’t rub in the wrong spots. Blisters are not fashionable.
  • When searching for a bag to travel with, try to imagine everything that you might want to carry around with you. An abundance of pockets comes in handy, as well as zippers to fully enclose, ensuring no valuables can accidentally slip out. Don’t choose something so heavy and large that it is awkward to carry or causes you pain, but be realistic, too.
  • On the note of purses, I firmly believe the best option is a cross-body; it gives you the opportunity to be hands- (and worry-) free! Beware of backpack style purses: though they may be easy to carry, they don’t leave your belongings within an easily accessible reach. Not to mention, a crossbody bag can be pulled in front of you in order to keep an eye on it, in case you suspect any sneaky pick pocketers are in your prescence. (Bonus tip: most museums ask that those carrying backpacks wear them on their front sides (on your stomach) so as not to turn and bump a piece of art. If you don’t want to be forced to carry your belongings like they’re your unborn child, maybe think again before you bring a backpack.)
  • When traveling, you aren’t going to want to bring your entire collection of bracelets and necklaces with you- imagine the tangled mess! Focus on a few key pieces that you can wear multiple times throughout your trip. It also helps to stick to the same scheme (pick either gold or silver) so you can mix and match from day to day, reducing the amount of jewelry you have to pack (and untangle)!

When you look good, you feel good. And when you feel good, your trip will be even more memorable. Happy travels!!

Are there any fashion essentials that you never leave behind when traveling? Leave me a comment below! 🙂



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