Outfits to Meet the Family

Whether you’ve been dating a while, or perhaps the timing just seems right, having your S.O. invite you to Thanksgiving with their family is a big deal (spoiler alert – even if they say it’s not, it is). This is a level of trust that needs to be respected. This person whom you care about deeply is allowing you in to an event that is reserved for family and trusted friends. Out of that appreciation, it’s only fair that you dress appropriately. Does that mean wearing something completely not you? Absolutely not. But consider approaching your outfit like you would your first date. A good first impression goes a long way.

Lucky you, we’ve put together 7 fantastic outfits that are stylish, yet comfortable and easy as…pumpkin pie.

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If your S.O. family venture takes you towards the Central or Eastern U.S. area of the country, you can expect to enjoy a very “traditional” Fall weather temp. That means lots of gorgeous foliage, and more than a little freezing rain and possible snow, to go with it.

Not sure what to bring? Here’s some inspo from our Editor’s curated collections…


Dressing for a winter wonderland starts with a warm pair of blackout tights and a just above-the-knee pair of soft suede/stretchy Lycra boots. Then we put together some of this season’s big trends – tweed, puff-sleeves and pearls. Together with a fun print mask (portion of the proceeds donated to Frontline Foods, an org supporting local restaurants to provide meals for workers on the front lines) and you’ll be humming “Let it Snow” in no time.



Fall 2020 is all about chunky, from sweaters to shoes to jewelry. This reversible, chunky sweater dress by Lulus can be worn either with the V neck in the back (perfect for when you want to rock a sexy look) or flip the script entirely and style it in the front like we have. Just like with your favorite ‘white shirt under your sweater’ combination, we’ve added this mid-calf length, white collared shirt dress under the sweater dress. Keep the warm feels coming with a pair of fleece lined tights and some rain proof combat boots (we fell in love with the plaid patterned ones above). Add some chunky chains (the set above is from Baublebar and is a total score), and a stylish woven multi-layer mask from Everlane. We’d be remiss if we didn’t point out that while chunky is in, bumpy is not…so add the Wacoal Ultimate Side Smoother bra to this list and put the kabash on those annoying back rolls.



Fall and corduroy go together like cocoa and marshmallows. We also love how effortlessly these burnt orange ones from Paige pair with this mauve puff-sleeve princess sweater from Hyfve. Take no chances with slippery sidewalks with these dark berry-colored, chunky lug soled booties from Sam Edelman. With its fun, bright print, the J. McLaughlin Think Pink mask was practically made for this outfit (also fun? 10% of proceeds will benefit Breastcancer.org). Keep things smooth under your knit with a T-shirt bra (this one by Hanes is spot on) and for all those extra items you’ll need when you’re routing around, the Alicya backpack by Tous is just the right size.



So how about if your travel takes you to the upper Midwest or Great Lakes region? Well my dear, you are most definitely going to understand the difference between “cold” and “wind-chill cold”. Layering is your new best friend here, and as a general rule of thumb you’re going to want to expose as little skin as possible.

Having said that, you do not have to settle for looking less than amazing when meeting the folks. Here are our options…


Ultra-plush and cozy, this marled sweater has just a hint of metallic sheen in it. The elongated drape pullover top has plenty of give to let you decide how much to show. We coupled it with some equally warm leggings – this festive plaid pair, also from Boston Proper. Print-mixing is big for Fall, as are substantial boots (military, hiking, etc). The trick to doing it right it to keep within the same color family, as we did with these chic camo boots in dark grey and black. The thick rubber soles will keep you confident when navigating your way over snow and icy sidewalks. Plus, what are the holidays without a little bling? Neo-Parisian chokers are hard trending this Fall and this delicate but eye-catching silver chain works perfectly with a drapey shoulder. And while you’re free to show your straps, a strapless bandeau will hold everything in place beautifully too. Last not least, a playful vintage print mask.


Skirts and sub-zero temps can co-exist. This gorgeous green, Vegan leather skirt is long and dense enough of fabric to be just as insulating as pants. Once inside, a cream colored half sleeve turtleneck will help keep you from getting too warm (an issue both real and faux leather can have). Underneath, keep things smooth with Kinx’s Wing Woman Contour bra. Water repellent boots will keep your feet dry and the thick rubber soles will keep them steady. Playing off the darker tones, the floral mask from Nicole Miller is just right. And of course, to add a little visual interest around the face, these pearl crawlers are a fresh update from the standard drop earring.



Some folks would say you pulled the lucky card if your travels take you to the West, South West, Hawaii or bottom South East of the U.S. These areas for the most part will allow you to enjoy the holidays as if you were on a spring vacation. Why not use this excursion as a way to treat yourself to a tiny bit of pre-shopping for the upcoming S/S 2021 seasons?

Here’s a sneak peek at two 2021 trends that you’ll get to enjoy right now…


Move over, Flame Scarlett, there’s a new hue we’re craving in 2021 and it’s name is Hot Pink. Already showing up in designers’ 2020 Winter collections, this uber-bright shade is surprisingly complementary to a variety of skin tones. Get a jump on this trend with a flare dress from Boston Proper. Bonus – this dress is a double-knit, wrinkle-resistant fabric, so it’s ready to go right out of the luggage! Complement your vibrant dress with a chic but neutral looking shoe, like this heel by Charles David. Gold hoops are timeless and versatile enough they may be the only pair of earrings you’ll need to pack. A dash of tropical on your mask adds a little fun. Keeping with your classic style dress, a curved silhouette bag is just the polished accessory to bring your outfit together. And of course, keep everything smooth underneath with some lightweight compression shapewear like this one from Yummie.


If your destination means you’ll be heading somewhere really warm, you may feel a little panic. After all, most of us have been settling into sweater weather so a little wardrobe paralyzation is to be expected. Cute and comfortable is key, which is why we fell in love with this sunny little number from Lucky Brand. The length is just right and the fabric is light and breezy. The tiny dash of eyelet on the top and bottom ruffle give it a sweet but stylish vibe. Keep the sunshine going with these adorable sandals from Katy Perry. The toe thong even has a cute little sun! And since you’ll be showing off those legs, add a little good luck your way with a Moon + Star charm anklet from Alex and Ani (to be worn to promote growth and new beginnings!). Round things out with a circular woven purse, an original art work print mask from ShopVida, and skip trying to hide the bra straps and try out the Third Love 24/7 Classic Strapless bra. Made with soft-support foam, it’s outfitted with a smooth band and silicone along the edges to stay in place without digging in. Don’t feel 100% going sans straps? Two sets of removable straps are included and can be added anytime.

No matter where you travel this holiday, we here at ShopLikeHer wish you good times and safe travels!

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