My favorite thing to do on a Friday or Saturday night is so pull up a stool at a bar and enjoy a drink. During the holidays, this need to pull up to a cozy restaurant bar, and have a quick bite to eat, is even stronger. Having a low-key yet stylish look is necessary for any casual date night during the holidays. You want to look relaxed, like you visit the place often, but also like you aren’t at the Olive Garden at 11 PM.
How to put together a good casual date night outfit:
- A well fitted skirt
- A basic blouse with a single detail
- A third layering piece (that is NOT a cardigan)
I always feel like I am either over dressed or under dressed to grab drinks. It feels like I am either showing too much skin, or not enough and then I just look out of place. I think I have found a recipe to vibe with the rest of the restaurant.
Casual date nights in winter are a struggle. I remember when I lived in Seattle, date night usually meant a Northface and my hair up in a bun because it was always raining! You have to ask yourself if it’s more important to look too-hot-to-trot but freeze your butt off; or, if you want to be cozy and risk not getting a call for that second date.
Being first date material doesn’t really matter to me. I guess I can chalk that up to being in a relationship for seven years. Now, I just like dressing up to match the vibe of the places I visit. It has become a fun ritual that my fiance and I do before we explore a new bar or restaurant.
Layering is your best friend when trying to find a relaxed yet elevated look for a casual date night. An outfit can be made with the infamous “third piece.” Without the vest this plus size outfit would simply look like a two-toned dress.
The vest in this outfit helps tie together the the loose-fitting turtleneck shirt and faux leather plum skater skirt. Even without the bow belt, this look would look casual-cool but for the sake of the holidays I put a bow on it.
Here are some third pieces you can use for layering this season:
- Chunky knit duster (don’t layer with a regular cardigan or risk looking matronly)
- Well fitted blazer
- Wool coat
So, I realize this look wouldn’t work for a lot of December nights or cold winter evenings ahead. I guess I am privileged and cursed by living in Southern California. I am privileged in that fall and winters are a mild 70 degrees on a cold day. That means I can play with light layers all year round. Sorry to all of the fashionistas that spend most of their days and evenings in a parka.
At the same time, those parka-swaddled fashionistas get to explore with warm winter layers. Fur lined hoods, wool knee-length jackets, and trench coats are all things I rarely get to play with.
Black OTK suede wedge boots – Target – $25
Plum plus size pleather skirt – Asos curve & plus size – $32 (get one like it here)
Black bow belt – Banana Republic – $20
Gunmetal clutch – Guess – $20
Grey statement necklace – Charming Charlie – gift.
Black sleeveless duster vest – Target – $15 (get one like it here)
Outfit total: about $117
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