Holiday Dressing

What to wear to all the fun holiday parties and gatherings? What to wear when you are out running all the errands and not look like a mess when you run into 100 people you know? I have the answer!
Here are my favorite go-to’s for just these occasions. I really like to shop local and try things on before buying them; I actually get things I’d normally not pick when shopping online! My favorite shops around me are Fred in Westport and Old Greenwich and the Darien Sport Shop. Great selection and wonderful customer service! Also, I love our local Lord & TaylorEverything is ALWAYS on sale, seriously. So if you live by me check out these local spots for sure!
So here we go! What I am wearing this holiday season to a “Holiday Party”, “Date Night”, “Girl’s Night” and daytime “Shopping & Lunch”! A bit of overlap as these are really from my closet. You may also see the word comfortable thrown around a lot; I am a stickler! If it isn’t comfortable, I am not buying it! Click on item name below to shop the look!


Holiday Dressing- holiday party


What I am wearing to a holiday party this weekend!

#1  Misa Los Angeles Anis Dress ($321)

My favorite part of this dress is hands down the grommets. They lend a little edge to a very feminine dress. Bonus: I think this is really a four season dress; perfect for a winter party but it could also be worn to a summer wedding with bright heeled sandals!

#2  Sam Edelman Telsa D’Orsay Pump in black suede. ($72 on sale from $120)

Quintessential black heel. Not too high not too low.  I am a big fan of Sam Edelman, good quality shoe at a great price. I rarely wear heels so these fit the bill for me!

#3 Rebecca Minkoff Glitter Leo Clutch ($95)

Pretty much the perfect little party clutch. Who doesn’t need a little glitter in their closet?



Holiday Dressing Date Night Out!

Date night out! I actually just wore this last Saturday when we went out to celebrate my birthday. Comfortable, chic and warm. I will be repeating this next week for sure!

#1 Velvet Alania Cold Shoulder Dress in ultra suede. ($218)

I may be a little late to the cold shoulder trend but I am digging it on this dress! Great sleeve length and again super comfortable.

#2 Jocelyn Knitted Fur Bandana with Leather Fringe ($175)

This was a birthday gift from my mother-in-law and it is amazing! So warm and so cute!

#3 Commando Ultimate Opaque Tights ($36)

Best tights ever. Period.

#4 Sorel Lea Wedge in black ($200)

I coveted these boots last year but never bought them. When they went on sale this Fall at Lord & Taylor I finally snatched them up. Best purchase, I wear them almost every day. The wedge is so comfortable and they look good with everything… even a short dress!

#5 Rebecca Minkoff Glitter Leo Clutch ($95)

This little number again. It is so cute!



Holiday Dressing Girls Night

Perfect look for a girl’s dinner out or a little Secret Santa gathering. I’ve already worn this top half a dozen times since purchasing it on Nordstrom’s big Black Friday Sale. Pulled together with out being too dressed up!

#1  Joie Amone Print Silk Top ($136.80 on sale from $228)

A good scale print on this little silk top. I love a little leopard… almost a neutral, right?

#2  JBrand Jeans Photo Ready Ankle Skinny Jeans in Blue Mercy ($218)

I bought these at the start of Fall (one new pair each Fall!) and have LOVED them. I wasn’t sure about the rips… too trendy? But I love how they break up the leg a bit, and they are so so so very flattering.

#3 Jocelyn Knitted Fur Bandana with Leather Fringe ($175)

I want to wear this with everything every day!

#4 Sorel Lea Wedge in black ($200)

I can’t recommend these boots enough! Perfect slip on waterproof boot that is still so stylish!



Holiday Dressing Shopping and Lunch

Now, what to wear doing all the shopping, errands, drop offs and pick ups? This has been my go to uniform. Again, COMFORTABLE is the name of the game here. All about the layers as you run in and out of places. And of course a huge tote to lug all your stuff!

#1 Athleta Revive Long Sleeve ($59)

I got these in a few colors during their friends and family sale because it may just be the perfect t-shirt. Fitted but not to tight; it is perfect under a sweater or on it’s own.

#2 Kinross Cashmere Textured Tunic ($395)

I try and refresh my sweater collection a bit at the start of every season. I always buy one really nice one and then fill in some holes at T.J. Maxx (you can get some AWESOME sweaters there!). I bought this one on sale but it really is worth the price tag! It is long enough to wear with leggings and so very cozy. They also made a cotton/cashmere version here.

#3 Athleta Sueded Strut Tight ($89)

Ultra suede legging that wears like a yoga tight? Yes please. These are pretty genius. You look super put together but feel like you are wearing sweat pants! I also love these moto ones and these are similar to the “leather” ones I bought years ago and wear all the time. Athleta makes the best “street tights” in my opinion!

#4 Rebecca Minkoff Medium Unlined Tote with Whipstitch  ($198 on sale from $295)

Classic black tote to stuff everything in when you are running around. I have had this one a while and it still looks new!

#5 Dr. Scholl’s Kinney Slip On Sneaker ($49.95 on sale from $69.99)

Dr. Scholl’s? Yes, really. They make the most comfortable shoes (obviously) and they have really stepped up their game on the style front! The high tops I wear everywhere are no longer available but these are similar. The black metallic are nice but so are the pewter metallic!

#6 L.L.Bean East End Explorer in kelp green ($179)

You are not going to beat the quality for the money with L.L.Bean. They have taken their classic looks and updated them with a more modern silhouette. Lined with quilted thinsulate;  it is a warm one. This coat has been my favorite!

Those are my current favorites, all the items I am wearing on repeat! How about you? What are your favorite pieces this season?


Please note: A Modern Housewife LLC has affiliate relationships with multiple brands. A Modern Housewife LLC will earn a small commission on any item purchased through an affiliate link. That commission keeps this site up and running and allows us to keep the content coming to you, thank you! All items linked are because  we own, love  and use them, or think they are of value to our readers (basically, we think they are pretty cool and want them ourselves!). Please let us  know  you have any questions about any products featured!







Leave a Reply