5 Outfits I Wore In New York City


I’ve said this before, but I am not your gal when it comes to curating the perfectly edited packing list…for anywhere. This Aquarius needs options, my friends. However, I have found some travel outfits that have worked really well recently.

That is what I’m here to share, the outfits I wound up wearing most in my recent trip to New York City in January. Did I bring too many things and not wear a big chunk of them? YES. Did I wind up repeating key pieces I did bring? Also yes. (Especially this and these!) And that is where we’re gonna land in this post today.

The Pieces I Wore Most In NYC: 5 Go-To Outfits

You’ll see at the end of the article I’ve included some fun places we visited this time on our trip–from eateries to museums, thrift shopping and a phenomenal journey on one of the Tenement Tours (highly recommend.)

But first, I’ll break down the outfits I wound up actually wearing and the pieces that worked best. We lucked out that it wasn’t too terribly cold or snowy while we were there, but layers and good coat choices were key.

1 | Travel Outfit For The Airport

Travel outfit, airport outfit

Similar Coat (or this!) | Sweatshirt (S) | Pants (M) | Boots | Bag | Suitcase

The What: I paired my lug sole Chelsea boots with the comfy Frank + Eileen Catherine chic sweatpants (and my fav compression socks underneath!) My Anine Bing tiger sweatshirt is a standby for me and in a size fitted enough to wear under my camel coat.

This roller bag and duffle (both from Calpak) are my new favorite setup ever, and I’ve been a backpack gal for years. See that large water bottle pocket on the side of the bag? YASSSS. For NYC though, if you need to walk with your bags a lot, I might suggest just bringing the duffle to put on top of your checked bag. We had access to a rental car the whole time so it wasn’t necessary for me this trip. Of course, if you are great at packing you’re probably bringing a full sized carry-on instead LOL.

The Why: I always try to wear some of my heaviest pieces on the plane, but I want to look put together and be comfortable, too. This combo made me very happy…that it looked thoughtful but felt comfy. The Frank + Eileen pants looked great even after the 5-hour plane ride, too! That’s one of the reasons we love them.

2 | Brunch + Sightseeing On The Lower East Side

New York City outfit, brunch outfit, sightseeing outfit

Coat (M) | Sweatshirt (this season’s version) | Pants (29) | Sneakers | Purse

The What: If you have a soft comfy pair of faux-leather pants, like these from Gap, I highly recommend them for travel. They hold up to rain or snow well and you can literally wipe them off. Yes, they are warm, and they were perfect for being out most of the day and looked chic for our early dinner!

This Athleta Whisper Featherless Puffer coat was perfect, too. It packed flat in my suitcase and isn’t too thick to travel with. The collar is amazing and prevented me from having to deal with a scarf all day. I LOVE that the back is long enough to cover my butt too (see the pic below in the itinerary section for a back view.)

The Why: Black is always my go-to for New York trips, but I don’t want it to feel boring. Faux-leather jeans wound up being the best pants I could bring on this winter trip and the thin quilted puffer was easy to pack and great to wear. Comfy sneakers I love in darker tones are great for walking around the city and more seamless with the jeans.

3 | Museum Day at the MET

New York City outfit, museum outfit, The MET

Coat (M) | Sweatshirt (S) | Similar Pants (or here) | Boots | Purse

The What: You can see this outfit is a similar concept to the one above, but here I’m wearing wide leg faux-leather pants (another piece I wore multiple times…these are a similar cut to my old Zara pair and well-reviewed) and my Ganni lug sole Chelsea boots that I adore for city + winters.

The Why: A graphic sweatshirt here (these are pricey, but literally my favs and I’ve worn them a TON of times) keeps the look feeling sporty/cool like I like, instead of just relying on a solid color top or sweater.

As far as shoes, we wound up not being out too much in the rain like I thought, so any chunky comfy black boot would have been great. But the lug soles on mine are on trend and add a little height for me. They’re still easy to wear all day and I can fit thicker socks under these for the winter months.

4 | Shopping in Brooklyn

New York City outfit, sightseeing outfit, shopping outfit

Similar Coat (or this!) | Similar Sweater | Similar Pants (or here) | Sneakers | Purse

The What: First off, if you want a purse that hugs your body and kinda feels like an emotional support purse, get the Moyen Messenger from Clare V. (See me here in front of my fav store to visit, always, in NYC or LA) I’ve had mine for well over a year now and it’s the best. It packs flat in my carry-on so I don’t get docked for too many items getting on the plane and then is the perfect size for a day in the city. I even have a tiny umbrella in it.

The Why: This day wasn’t as cold and we were going to a nice dinner that night, so I opted for my camel coat.

Again, I love a little stripe or graphic print for my tops to add that bit of interest, instead of just a solid. Gap’s spring version of my sweater looks great. My trusty Nike Dunks look great with both the straight leg and wide leg pants, so they were a good option, too.

5 | Dinner + Drinks Night in Brooklyn

New York City outfit, dinner outfit, nighttime outfit

Similar Coat (or this) | Similar Shirtdress | Similar Pants (or here) | Similar Boots | Purse

The What: Since we had our car (and not just a hotel to pop back to) I brought along my white boots, a long shirtdress and a pashmina to swap into for dinner. The wide leg faux leather jeans meant I didn’t have to bring a separate dress pant and they were super fun under the maxi shirt dress.

The Why: While I do tend to pack too much, I love finding an easy day to night outfit combo that works like this one did. I think since I’m not a dress person this is always a little trickier to navigate, but this shirt dress + wide leg pants + white pointed toe boots pairing could work in a variety of colors, patterns or specific pieces. I do think a longer coat here is also key. I will be repeating this combo for sure.

Our Mini New York + Staten Island Itinerary

For those interested, I wrote just a quick little summary of the places we visited on this trip, giving a shout-out to my new East Coast home-away-from-home, Staten Island. Fight me, but they have the best pizza ever.

New York City weekend itinerary
Clockwise from top left: Beastie Boys Square, Books Are Magic BK, Russ + Daughters Cafe, Royal Crown Bakery SI, Degas at the MET

Day 1: Travel (yay for direct flight from PDX to JFK!) and pizza at Lee’s Tavern Staten Island (best bar pies around)

Day 2: Lunch at Royal Crown Bakery (get the mortadella hero, pignoli cookies, and mini cannoli), then off to Brooklyn –> Books Are Magic, Kule, Clare V, thrift shopping at Plus BKLYN + 2nd Street Dumbo, martinis at OTB and dinner at Francie (plan ahead for reservations…thanks to our friend Aaron/head chef/and owner of St. Jack Pdx for the hook up. Get the blinis + caviar and the pastas!)

Day 3: a day on the Island…Totenville for thrifting at Nothing New, Richmond Hood Co – cool skate shop for tees + beanies, Killah Koffee Shop (if it’s a Saturday…#wutangforever) smoothies + snacks at Vodega (vegan bodega) + dinner at Pastavino.

on andrea: Similar Jacket | Similar Jeans | adidas | Socks // on me: Jacket (M) | Jeans (29) | Sneakers

Day 4: Lower East Side day starting with brunch at Russ + Daughters Cafe with a stop for babka at the deli around the corner, phenomenal tour at the Tenement Museum (loved the 100 Years Apart featuring 2 women working in the garment industry in 2 different centuries,) pics at Beastie Boys Square, more thrifting, dinner at Saigon Social (thanks to @nom_life for the rec!) and ice cream back on SI.

Day 5: a trip to the MET to see Women Dressing Women (do your best to get there for this!) and some amazing classics, lunch at Nectar Cafe classic Greek-owned diner (tuna meltsss) and then another stop on the way back at Royal Crown Bakery for cookies…and back to Lee’s Tavern for more bar pie pizza because we couldn’t resist.

Day 6: Back to the City to explore a bit on my own (while my bestie Posy took her Pop to some appointments) I hiked over to The Morgan Library + Museum (stunning) and then up to Bryant Park to the Public Library (there’s a cool free Treasures exhibit right now.) I freaking love NY.

I hope this is helpful as always in what to wear to NYC or what to see! Or perhaps you’re traveling to a different city during these colder months…I think these outfits would be equally appropriate. Let me know of any favorite West Side spots I need to hit up next time!



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