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How to Dress for a City Vacay

As a fashion enthusiast who has been to the Big Apple many times, I feel it’s my responsibility to share my knowledge of what New Yorkers actually wear. This is a ‘Pensacola-ns’ guide to “How to Dress for a City Vacay”!


When traveling this spring and summer to any large metropolitan city, here are 5 style tips to both blend in and stand out. Headed to dinner? the theater? walking around a museum? or just grabbing a cocktail with your girls? This is the article for you.  

One of the first things you have to know is that New Yorkers love to walk. When visiting the city I highly recommend walking anywhere that isn’t more than 2 miles away. This way you can explore the area, and you will undoubtably find the cutest family-run bagel shop, the freshest bodega, and the best one-stop espresso shop. You also get your cardio in, so it’s a win-win! But what does this mean for your packing essentials? A pair of comfortable and fashionable sneakers are vital. Whichever pair you choose will need to be worn interchangeably with pretty much every outfit variation in your suitcase. One of the best parts about New York style is that you can keep things casual, as long as the look isn’t sloppy you can take your sneakers from walking all day straight to an evening glass of wine. These are a couple of my favorites for both comfort and stylistic versatility. 

Macey’s Recommended Sneakers: Aurty Low-Top Sneaker and The Classic Veja Sneaker 

We are talking about traveling to New York in the spring-time and although as Floridians we love bringing out many light colors and patterns in our spring wardrobe, New Yorkers wear black. And it’s not because they are angst-ridden or afraid of a little color. In my time in the city I’ve realized black is not only an easy way to keep you looking chic with little to no thought, but New York can be dirty! I mean seriously, if you head out in the sort of all-white linen “look” we can easily sport in Florida, you will most-likely come back looking like a sewage rat. I’m not saying no to all color, but I prefer to stick to black and mix in neutrals so none of my clothes get ruined from street debris and muck in the air. For your trip, let’s leave the resort-wear at home, and take some inspiration from Hailey and some of my picks. 


Little black dresses are far from a secret, but they really do become heavy hitters in the spring and summer in New York. Not only do they stick to the all-black aesthetic, but they’re also versatile. You can easily dress up a black dress with heels and a leather jacket or down with sneakers and a jean jacket for Saturday brunch. Any black dress with a streamlined silhouette will have you fitting right in, either in Williamsburg or the West Village. 

Macey’s Reccomended LBD: The Perfect Classic LBD and LBD with A Modern Feel

BRING YOUR CUTE HEELS AND SANDALS IN YOUR BAG!!! Here’s a style secret for you: New Yorkers love to keep a spare pair of sandals or flats in their bag to spruce up their outfits; they simply wear comfy sneakers to commute and then swap their shoes once at their destination. This tip has been a foot-saver for me during my time in New York. I am not one to sacrifice style for comfort, in downtown Pensacola I will sport my stylish heels with absolutely no back-up shoe. In the city, things are different. In New York, if you don’t wear comfortable shoes, you will not be able to enjoy so much of what the city has to offer on the superior form of transportation: your chevro-legs!  

Macey’s Reccomended “Purse Shoe”: Sexy/Chic Everyday Sandal, Fun Metallic Sandal and Trending Minimal Mesh Ballet Flat

Keep your outfits simple and change it up with fun accessories. A classic belt goes a long way these days keeping you looking put-together and classic while remaining on-trend. New Yorkers are usually dressed somewhat casually yet look put together because they have great basics in their rotation and fun accessories like the “mini bag” (which was really hot last summer). I believe going into this spring season we are going to be seeing bigger and slouchier bags gracing the streets. I am excited about this shift, because that means you have more room in your bag to be prepared for whatever the city throws at you. Change up your look with fun eyewear. Sunglasses are a must in springtime in the city. You need to keep your eyes protected from the glare of sunlight bouncing off the glass buildings that line the streets – fashionable and functional. Accessories take up very little room in your suitcase and make it easy to style and switch up looks organically when you arrive in the city. I’ve selected a bunch of my favorite accessories that would look right at home in the big city and compliment your existing wardrobe. 

Macey’s Reccomended Accessories:  Spring Sunnies, Baseball Caps are Hot, How cute is this Claw Clip, The Perfect Summer Tote and Highest Quality Seasonless Tote