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 or Christmas dinner 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 10 fantastic outfits that are stylish, yet comfortable and easy as…pumpkin pie.


If your S.O.’s 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.

Nothing beats a classic put-together look. Start with Windsor’s wrap knit dress and then slide into a pair of dark cable knit tights. Next we add these cool knee high boots from French Connection (the unexpected pattern on heel makes them so fresh). Baublebar’s Y-chain necklace can be personalized with your initial in pave crystals for that unique touch and finally, Stella McCartney’s super chunky chain bag is a perfect medium size for carrying all your necessities in style.


When you need to just jump into it, have some fun with autumn’s moody palette, namely burnt oranges, reds and browns. A wide leg jumpsuit from Windsor is the anchor for the look, which we pair with a swirly-patterned mesh top. Circus NY’s decadent cognac colored booties will give you solid footing, and for accessories we add this fantastic tapestry-inspired hobo bag and a little bling courtesy of Eye Candy LA’s drusy agate bracelet.


Show off your love of rich wintry color blends with this next fit. A marvelous marbled midi sets the stage and pairs perfectly with a pair of dark wine booties from Coconuts. Elie Tahari’s buttery hobo bag and some luxe accessories complete the look.

From Left to Right:

This color combo of autumnal browns and sweet neutrals is a surefire fit that is also super comfy. The cream Pointelle knit sweater evokes all the cozy feels and pairs amazingly well with Windsor’s silky pumpkin midi skirt. With a nod to this season’s big boot obsession, these western style knee highs from Bellini are stylish and sturdy. All that’s left is to complete the chic by adding Dooney & Bourke’s new season shoulder bag in dark brown and of course, bring on the bling with Baublebar’s tasselling rhinestone earrings.




So how about if your travel takes you to the upper Midwest or Great Lakes region? Well, 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…

Skirts and sub-zero temps can co-exist. This gorgeous faux leather skirt is long and dense enough of fabric to be just as insulating as pants. Once inside, a soft gray cashmere sweater brings the chic. Keep things moving with Clark’s comfort boots (the inner lining will keep your feet warm and the thick rubber soles will keep them steady). Finally, we go sleek silver with Mica’s statement big drop earrings, and even more metallic bling with Nina’s gunmetal crescent bag.



Go classic chic with this next ensemble. Wide leg pinstriped pants pair with a cozy cream-colored cashmere crew to set the stage. Some chunky, bejeweled loafers from G.H. Bass and Marchesa Notte’s crystal statement necklace bring the bling. We complete the look adding a little color pop in a big tote, namely M. Gemi’s The Elena, which is roomy enough to hold any cold weather essentials.


Is there a lot of relative-hopping happening? Going in-between several family stops calls for a cozy casual fit. This Henley bodysuit and dark wash jeans combination is a great staple look. To it, we add a solid pair of winter boots, namely Palladium’s Pampa Sport. Shearling lining inside and waterproof outside, and grippy rubber soles make this boot the perfect choice. For coverage when you need it, Summersalt’s soft spun cashmere sweater in sweet pastels will wrap you in luxe comfort. Finally we add a pair of multi-colored natural beads to bring the whole fit together beautifully.



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 2024 seasons?

When in doubt, the LBD is always your best friend. This a-line mini version by Windsor is so chic. Keeping with the casual daytime vibe, we pair it with some cute, rose nude heels from Nina and a fun, plaid top-handle purse from Cato. For the final accessories, we go silver with Zoe Lev’s modern silver bar earrings, a charming silver necklace from TOUS and we layer it with Splendid Pearl’s blushing pink pearls.


Lightweight fabrics are a smart way to look great in the heat. These airy, satin cargos are a cool, casual option, especially when paired with Summersalt’s super soft French terry puff sleeve top. Mansur Gavriel’s dreamy sandal from their S/S 2024 collection adds a fresh note, and we finish things off with a fun, sequined hobo and some statement hoops.


Cute and comfortable is key, which is why we fell in love with this sleeveless midi. The length is just right and the fabric is light and breezy. Keep the beachy chic going with fun, tasseled tote and a pair of oh-so-comfortable sandals from Birkenstock’s Papillio collection. Finish it out with a pair of dripping sophisticated shades from Knockaround’s new Deja View collection in Rose Latte and 18k gold plated disc earrings from RockFlowerPaper.



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

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