I can’t believe today is the last day of November! I love this time of year when everyone starts to do more entertaining at home and the countdown to Christmas is officially on. Here are four occasions we have on our calendar — family dinners, an office party, friends’ cocktail parties, and a winter wedding — and a few of the dresses I’m considering for each. I’d love to hear what special occasions you have coming up!

design darling holiday dress guide for family dinner

Sail to Sable shift  //  Vineyard Vines plaid dress  //  DVF wrap dress  //  Tory Burch sweater dress

Our family dinners are definitely not a formal affair, but it’s nice to feel put together for special occasions like church or Christmas Eve dinner. I love the idea of layering a white button-down like this one underneath a tweed shift dress, and you’ll never regret investing in a DVF wrap dress — they’re comfortable, classic, and look good on everyone.

what to wear to office holiday party

Eliza J knit dress  //  Draper James fit-and-flare  //  Kate Spade bow dress  //  Milly bell sleeve dress

I know office holiday parties can run the gamut from casual team dinners to over-the-top formal affairs so clearly these picks fall somewhere in the middle of the spectrum. It’s important to consider the venue and if possible get in touch with other attendees to make sure you’re in the right ballpark, whether it’s your office party or you’re going as a +1. I never want to be the girl who shows up to a steakhouse in a ballgown or to a museum in a pair of jeans! A cocktail dress that’s not revealing is always a safe bet, and I love the looks of this one and the price tag of this one.

holiday cocktail party dresses

Amanda Uprichard dress  //  Milly dress  //  Tuckernuck dress  //  Draper James dress

Is there anything more fun than getting an invite to a friend’s holiday cocktail party? I love any excuse to get dressed up and spend time with people I love and wish we had a few more weeks to get settled in our new house so we could have our own party this year! I think this short-sleeved dress with the flounced hem is just the cutest thing ever. It needs to come live in my closet! (And it’s available in two more colors here!)

what to wear to a winter wedding

Nordstrom midi dress  //  Fame & Partners bow dress  //  J.Crew sequin dress  //  Cameo strapless dress

I’m still trying to talk myself out of ordering a new dress for my cousin’s wedding this weekend (why do I always wait until the last minute?!) because I am in love with this ballerina-esque midi dress and this sequined slip. I magically have a dress in my closet that I’ve gotten to wear to three weddings because there’s been no overlap in the guest list so I think that’s what I’ll wind up wearing this weekend… but really, wouldn’t I find a dozen excuses to wear this beauty?

P.S. Not to get too ahead of myself, but I’ve been eyeing this sequined number for New Year’s Eve. Va va voom!

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