No. 150: Everything We Wore, Ate and Enjoyed in New York
Because few things are more magical than New York in the Fall
In every Q&A I’ve done, at least one person has said, “what should I pack for a Fall trip to New York?” Before I knew I’d be on such a trip myself, my first answer was always, “Me. Take me with you.” Now that my own September trip to one of my favorite cities in the world is behind me, I’m here with your perfect pocket guide. This post is too long for email so be sure to click ‘View More’ at the end or see the full thing right here.
What We Wore:
The sole purpose of this trip was styling my sister Jackie for NYFW. My main goal of every trip is to feel put together and flex a different muscle than when I’m home rotating the same few outfits and multiple matching sweat suits. Dusting off favorite outerwear, saying yes to a heel if need be and saving the sweats exclusively for evening walks around the neighborhood is always a fabulous feeling. I’m typing this in my favorite Spanx sweat set so the “real pants every day” commitment was short lived, but it really did feel great at the time.
My role for this trip was to be “husband.” I’m naturally an over-prepared person, but I wanted to make it my job to be even more so. To always have extra snacks and hydration so she didn’t have to worry about it, to carry the cameras and heavy things, to make life as simple as possible so Jack could be the talent. This meant that the trip wasn’t about my outfits—90% of what I wore I’ve owned for 2-10 years—but about her new exciting looks. Relying on wardrobe staples is so comforting to me and the reason I always tell my clients and anyone who will listen to invest in a cohesive wardrobe rather than in “moments.”
The sweater I’m wearing here is one of the top 10 most worn pieces in my closet. I’ve had it for almost a decade and was shocked to see Anthropologie still sells it. It’s so lightweight and cozy that after a couple years of reaching for it more than anything else, I finally bought a second color. These pants are a fairly newer purchase I was convinced to try after seeing them looking incredible on more body types and sizes than what I’m used to. They feel like pajama pants while looking super cool and that’s an eternal no-brainer for me.
Almost everything here is old, too, with the boots being the only exception. These are one of the very few items I ended up keeping from the Nordstrom Sale this summer and I will say—they’re fantastic. I walked all over the city playing husband in these things and felt wonderful despite my wide feet trying to keep me from being great.
A barn jacket with linen pants is my go-to transitional Summer to Fall look. I have the version of the pants without the drawstring, but I wish I would have grabbed the drawstring version because I like them oversized but they’re much too big in the waist. A hair tie is holding them on, to be honest here.
Ignore the mascara on my eyelid and only pay attention to the linen pants with white tee under v-neck sweatshirt. That’s what I hope you recreate as long as it still feels like you’re halfway between two seasons where you live.
You know this denim trench well, friends. I remember getting messages about the price when I first started sharing it three years ago and my answer was always, “I know, trust me. But I will always invest in high quality pieces that are done so well that I’ll wear them forever.” And the brand has since closed, the resale prices are sky high and I wear this thing all. the. time. Some things truly are just worth it. This formula of a dress shirt, trousers, a trench and a loafer is so timeless and simple to wash, rinse, repeat. I could add one of these Polo socks which I wore the next day and a full loafer, I could have worn a different trench, I could swap a neck bandana for a scarf over my shoulders—the opportunities are endless.
I had picked this blazer dress as a moment for Jack’s MMG party and the Revolve party, but completely forgot that I needed to be with her and dressed, too. The only dress I currently own that a. fits and b. is club or “out-out” appropriate is this blazer dress I wore to a friend’s wedding five years ago. Not buying anything for myself was quite the challenge, but I did live to tell the tale.
Her dress in both colorways is genuinely incredible but only if you use this styling tape and potentially this boob tape kit. I used them constantly during this trip. I can’t recommend the freedom of a blazer dress enough so if you have an upcoming occasion and you want to feel your best, this round up will be your best friend.
This skirt with a Dissh blazer was a favorite moment of the trip. Jack confirmed it’s not itchy and we put this Spanx underwear underneath, though the blazer more than covered her bum. I can’t recommend it enough as a show stopper moment.
The amount of fabric in this look is nothing short of amazing. My sister was stopped countless times by strangers on the street asking where they could buy her outfit which tells you just how stunning it is in person. This was certainly the investment outfit of the trip, but was the perfect choice for a ShopMy event.
Also, a quick word on my yellow bag in these photos—I’ve been stopped countless times to talk about this bag. I invested in it years ago and the yellow sold out almost instantly. She’s a pricey gal for sure so this isn’t for everyone—just those asking. I found it for resale in yellow (which never happens!!) right here and available in green here, black here and grey here. A look for less version is this one right here.
All my recent outfits and the outfits (that are linkable) are on my LTK.
What We Ate
This was a completely other New York experience because we were required to be in different boroughs with strict timelines so we couldn’t just spend a whole day in one area, eating our way through the city. We did hit the places I always visit whenever I’m in New York: Butcher’s Daughter for the most delicious health food (and the place where the yellow checker photos were taken) where I always get a vegan gluten-free pizza, raw juices and a perfect latte, Maman for gorgeous, delicious coffee and breakfast, Sweetgreen every day (highly recommend going to the 30 Rock location if you’re nearby and taking your salad outside to eat in Rockefeller Center) Balthazar which I fell in love with in London and makes me feel like I’m there and we walked to Van Leeuwen every day for a scoop of vegan ice cream with vegan hot fudge. Unreal. We also stopped my Ladauree which is an essential in my book, but this time specifically because Keogena’s birthday fell during this trip and her only request was a box of her favorite macaroons. If you can sit down for breakfast, O and I (many lifetimes ago) ate the French Toast at Lauderee in New York, Paris and Rome and every single time we ate it, we said “this is the best thing I’ve ever had.” I bought their cookbook and now know how to make it at home as a special treat.
I usually love to visit Jack’s Wife Freda, Nobu and would fight for a Polo Bar reservation but this wasn’t the trip!
The NYFW Brands provided some pretty delicious food, but Target absolutely took the cake with the best ribs of my entire life. Unsurprisingly, Jackie and I were about the only two people eating at the entire event but as we Singletary girls always say, more for us! Bouchon Bistro was a new to me restaurant. I felt like the luckiest girl on the planet because Jack had a gifted meal and I did nothing to deserve a lunch this unbelievably delicious. It’s very French—Jack ordered lobster pasta, steak frites (she said the best of her entire life,) and crème brûlée. They accommodated my dairy and gluten free dietary needs beautifully and my chicken with vinaigrette and shoestring french fries were unreal. There was also, conveniently, a street fair happening in Soho where we were staying and we wandered down there every night so Jackie could get a slice of pizza made right on the spot and some fair foods. Between that and our Whole Foods trip for protein shakes waters and snacks, we were so well fed and I already miss the food too much.
What We Enjoyed.
+ That first step into Central Park will never lose its magic. We stayed in Soho which I always recommend, so the first chance I get once we arrive in Manhattan is to make a beeline for Bethesda Fountain. There’s always someone singing, (a goosebump inducing performance of Ave Maria was the treat this trip) the paddle boats make for great people watching and the whole thing is a bit euphoric.
+ Walking 15K steps in uncomfortable clothes, coming back to the hotel to switch into sweats and sneakers and walking around the neighborhood is a feeling that needs to be studied.
+ The shopping is Soho is unmatched, always.
+ The FAO Schwartz in 30 Rock is overwhelming, bustling, ridiculous and absolutely necessary. We came home with a little something for all the kids and it’s always a favorite stop.
+ If you can spend even one night at 1 Hotel Central Park or Brooklyn Bridge, I beg you to do it. Use points, budget, save pennies, it is absolutely worth it. (We stayed at the Moxy this trip, but O and I have loved our 1 Hotel stays in the past.)
If you have an upcoming trip to New York, I’d love to know what’s on your agenda and I hope this helps inspire at least a couple outfit formulas for an easier trip. Don’t forget your noise-cancelling headphones, ear plugs, comfiest sneakers and baseball cap, you’ll thank me later.
Your hat/blazer outfit is iconic I screenshotted it to recreate! We’re going to NYC in January and you gave me great food recs 🫶🏻 can’t wait for the vegan icecream!
I love this BTS look into your trip! It looks like it was so much fun. Penciling down the restaurants you mentioned for future use. My girls have dairy allergies, so food and traveling are not always easy for us either!