“Start spreading the news…I’m leaving today…I want to be a part of it…New York, New York”

So I just returned from a four day trip to New York.  From dinner hosted on a penthouse terrace to drinks at a jazzy speakeasy….it was definitely a posh weekend!  

One of the highlights of my trip was dining on the 10th floor outdoor terrace at a dear friend’s penthouse in midtown.  So, what do you wear to a penthouse dinner party in mid-July? Something penthouse posh….of course! For this special evening, I wore a floral tiered maxi skirt with a white off-the-shoulder top tied at the waist and brown sandals.  Be sure to take a look at the penthouse terrace views on our Pinterest board!


 Whether you are going to a museum or taking a leisurely walk on the High-Line, one of the best ways to look posh in New York is with neutrals.  A pair of wide leg khaki pants paired with an oversized white shirt and white bucket bag will give you an updated contemporary look. To add a fresh summer vibe to your city style, think about carrying a white handbag or tote.  Two of my favorite totes for city shopping are a large white Goyard and a Tory Burch canvas tote….both perfectly posh!

Please know, sneakers are not only perfect for city strolling but also super trendy. A pair of sneakers is exactly what you will want to pair with a dress when strolling street markets.  We think the black and white polka-dot dress paired with black sneakers and a wicker handbag on our Pinterest board is super city-sleek! Another way to accomplish a casual city look is to wear a dress with animal print sneakers.  Because you know what they say about the city….“It’s a jungle out there”!

My second night in New York, Chris took me to a fabulous speakeasy. Tomi’s is a jazz bar where you enter below street level, walk down a dingy hallway, and ring a door bell to enter….a very hip New York experience!  To add a little “sex and the city” style to your New York nightlife, we suggest a floral V-neck wrap dress. If you want to get out of the sweltering heat, just grab an Uber, and that way you can stay cool, look fresh, and wear your strappy heels.  How posh does that sound?

For a Sunday church service, brunch, and a Broadway matinee a white and brown ensemble is so sophisticated.  To up your cosmopolitan style, think about wearing a white linen dress with ruffled shoulder straps complemented with a brown belt and macramé Staud bag.  We are loving a pair of flowy brown pants, oversized white blouse and a wicker bag with a scarf. And you can’t miss with khaki crops or culottes….yet another way to keep your New York style current and on-trend.  

FYI….a white ensemble will always give you posh points!  My favorite “up-town girl” pick shows a lady wearing a strapless white jumpsuit with a light camel jacket draped over her shoulders.  We’re obsessed with a head-to-toe white pants outfit featuring a bright green handbag….the perfect pop of color. There are so many great looks on our Pinterest board that will take you from an artsy lunch at The Whitney to the fabulous bar at the Four Seasons.  Don’t you just love posh points?

Whether your city travel style is casual or posh….be sure to check out all the options on our Pinterest board!  And “start spreading the news”!!!

Holley Williams is a personal stylist specializing in closet inventory, seasonal shopping, closet organization and wardrobe consultation.  Contact Holley at [email protected].   Be sure to check out Holley’s updated Pinterest board here.