Holiday Season What-to-Wear: Drinks with Friends

Your friends want to get together to (eat,) drink, (and be merry) before the family events, stocking stuffing and snow storms book everyone solid through January. Everyone is getting a little dressed up, but not necessarily party-like-it’s-your-birthday dressed up. So, what are your options?

Let’s talk inspiration first. You want to look like you just tossed this outfit on, ran out and the door and BAM! Look who’s fabulous? Like so:

Holiday Season: Drinks with Friends Inspiration

The idea here is similar to the WtW Office Party edition: one or two areas of sparkle. Unlike the office party, however, feel free to rock a mini. Show some leg, but slip into a pair of opaque tights because a) it will chic things up a notch and b) it’s December. A black blazer is a killer addition to the outfit– it balances out the glitter/prissiness of the skirt with a cool city girl vibe.

My version:

Holiday Season: Drinks with Friends

1. Honeydew Intimates Lace Back Camisole ($24)
2. Seventh Door Studded Double Finger Ring ($58)
3. Juicy Couture Crown Pavé Stud Earrings ($84)
4. American Eagle Solid Tights in Black ($13)
5. Elizabeth and James Slick Suiting Elizabeth IV Blazer ($395)
6. Topshop Black Sequin Beaded Mini ($125)
7. Chinese Laundry Haylie booties ($84)
8. Kenneth Jay Lane Crystal Statement Necklace ($814)

The key to looking polished-but-not-overdone is typically a few areas of interest and keeping the rest simple-chic.

Start with a blank tank (1) and basic tights (4), layer with a slightly slouchy black blazer (the “slightly slouchy” is key– too tight and you’re Corporate Boardroom Girl, too loose and you’re I Have A Huge Upper Body Girl). I chose the Elizabeth IV blazer (5), because for me it represents the Blazer to End All Blazers. Perfect amount of slouch, a nipped waist, it’s long enough to extend the torso (great for short-waisted and/or busty girls) and has scrunched sleeves that add that touch of oh-I-just-threw-this-on.

The standout pieces are the sequined mini (6) and a statement necklace (8). Sequins are huge– you can find them everywhere from Net-a-Porter to Forever21, so there’s a mini out there for every budget. Same goes for the statement necklace. This Kenneth Jay Lane example is super pricey, but I’ve seen very similar versions at Express/Target/Charming Charlie for reasonable prices. I topped off the look with a double finger ring (2), pavé studs (3) and a pair of simple black booties (7). A black bootie + black tights give the legs the illusion of length– a girl’s best friend.

What do you think? What is your outfit of choice when meeting up for peppermintinis with friends?


  1. Oh my gosh, yes! This post just made my day. I’ve been seeing sequins everywhere lately and I’ve been wondering… “what’s up with that?”. Now I know! J. Crew has a few pretty, pretty sparkly and sequined items in their holiday catalogue. And since it’s J. Crew you know the prices won’t be too outrageous but the quality will be top notch.

    On another note, any suggestions on blazers for long torso’d ladies?

    Thanks for the fab post!

    1. Carrie- If you’re long-waisted, I would stick to a blazer that hits right at/just above the hips. If you go cropped or super long, things are going to look shifty. 🙂

  2. Love this look! Going out with girls from my hometown tomorrow- definitely wearing a variation of this! Thanks for the tips!

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