NYC Holiday Clothing Guide – What to Wear

I really can’t believe how close Thanksgiving is. I feel like it was Labor Day a minute ago and, as I left my office building today, I couldn’t believe that the Christmas tree and wreaths were being hung up already. Can we slow down and enjoy one holiday at a time please?  Anyway, I started thinking about the endless outfit possibilities for Turkey Day. Whether you’re relaxing at home with Mom and Dad, and watching the Macy’s Thanksgiving Day Parade, or you’re meeting your boyfriend’s family for the first time, here are some festive outfits that will carry you throughout the holiday season:

NYC Holiday Clothing Guide for What to Wear when you are Kickin’ it with Mom & Dad:

This comfy and cozy knit-dress is just what you need to survive a casual and relaxing day with your family. It’s a step up from pajamas but, just in case mom decides to capture the family holiday photo, you will be picture-perfect. Throw on these super warm fleece-lined leggings and I’d wear a pair of Boots like these for the photo-op but totally change into slippers for the rest of the day!

NYC Holiday Clothing Guide - Knit Dress NYC Holiday Clothing Guide- Leggings NYC Holiday Clothing Guide -  Chelsea Boots

NYC Holiday Clothing Guide for What to Wear when you are Meeting His Family:

Being introduced to your significant other’s family on any occasion can be daunting, let alone during the holidays. One bad outfit can be worse than chipping grandma’s heirloom teacup. Dress appropriately but stay true to yourself. You don’t have to go too conservative if that’s not your style but you should stay extra-polished and leave the low-cut sweaters and ripped jeans at home. One of my favorite trends of the season is The Midi Skirt. The length is modest but also playful and chic at the same time! I live in soft-wash flannels because they are so easy to dress up or down. I would tuck this plaid flannel into this beautiful burgundy jacquard midi skirt. (Pstttt….the sleeves are super easy to roll up when you are helping his mom wash the dishes!) Flats keep this look classy but a pair of black pumps would certainly kick it up a notch! I love the contrast between masculine plaid and beautiful jewels so throw on this feather necklace for extra flair.

NYC Holiday Clothing Guide - Midi Skirt NYC Holiday Clothing Guide -  Plaid Flannel NYC Holiday Clothing Guide -  Necklace NYC Holiday Clothing Guide - FlatsNYC Holiday Clothing Guide -  Pumps

NYC Holiday Clothing Guide for What to Wear around Mia Famiglia:

This is not a day for pants. Unless they have an elastic waistband. If you’re like me, and spending Thanksgiving day with your extended family, you like to dress up and look nice but also feel really comfortable to accomodate the food. All the food. I’ll probably go with something like this: a gorgeous embellished collar tee dress from Loft. I’ll be able to help my aunts cook. (I am usually tasked with side dishes but I am dying to try the Maple Pecan Bars from the Eat Up New York Kitchen!) This outfit is also great to run around chasing my little cousins, enjoy dinner, and all the while feeling festive and pretty. These booties are going to top off any outfit you have for this season.

NYC Holiday Clothing Guide - Collar Dress NYC Holiday Clothing Guide -  Booties

NYC Holiday Clothing Guide for What to Wear for Friendsgiving:

With plenty of New Yorkers who have to work the day after Thanksgiving, I hear all the time about people who don’t go home for the holiday (Lucky! Ahem. I mean. Oh, that’s sad). If you’re getting your turkey-fill by dining out with friends in a similar situation, or you’re meeting old friends from high-school on Thanksgiving Eve, this is your go-to look. Another trend I am obsessed with is the Peter-Pan collar. I’ve been waiting for this comeback and I can’t get enough. The soft, rounded collar is so sweet. Pair this blouse with this amazing plaid blazer (can we all agree that Thanksgiving isn’t the same without plaid?) and throw on these jeans or your favorite pair of dark denim. Add these glitter loafers for some sparkle and voila!

NYC Holiday Clothing Guide -  Plaid Blazer NYC Holiday Clothing Guide - Blouse NYC Holiday Clothing Guide - Jeans NYC Holiday Clothing Guide - Glitter Loafers

Need more styling tips? Email me at

Have a very Happy Thanksgiving!

New Call-to-action

About The Author

Chief Eating Officer

I see food - Everywhere. I eat, sleep, and drink up NYC as much as possible. It isn't always about what you see but how you see it - A brain that has seen the inside of the corporate world, the back rooms of the legal world, but prefers the comfort of a walk in cooler - Not everyone can appreciate the smell of a supermarket freezer.