Hi. Sorry about yesterday, but I have totally good reasons why I didn’t post.

I was making some holiday gifts for my friends (which I’m making a how-to for, but I won’t post yet, for fear that it will blow the surprise for my friends–stay tuned though!).

(Beautiful DIY gift wrapping tutorial here)

AND the most exciting thing of all, I got to go to my lover’s annual family bingo night. Seriously, it was fun; thirty people all playing bingo and vying for dollar store prizes–I won two bars of Irish Spring Soap and 100 count mini memo notes (which I’m pretty excited about)–while we’re catching up with family.

Which brings me to my topic this evening: what to wear during the holidays.

Because J’s [my lover] family is quite large, there are several events to go to during the holiday season. I’m no fashionista, but I’m a woman and I care about my appearance, so it isn’t really my style to show up to three events with almost the same people each time wearing the same thing.


(This woman actually is wearing the same black dress everyday for a year… Crazy.)

I like to keep it simple and sophisticated–but that’s pretty typical for me (whew, a little sassy, but… true).

Whenever I’m getting ready for an event there are always a few questions I ask:

-What time and where is the event being held?

-Who’s attending?

-What will we be doing?

Based off of the answers, I now know:

-How formal the event is–usually based on the time and location of the function

-How conservatively I should dress–if there are Grannies and other respectable elders/children hanging out I want to keep my outfit more modest and subdued

-The kind of outfit that is most appropriate for the activity we’ll be doing–if we’re going outside I know that I have to dress warmer or if we’re going to be physically active I probably won’t wear a dress/skirt

Now the line-up:

Casual Gathering

Velvet schoolboy blazer

(J.Crew Velvet Schoolboy Blazer)

This is basically what I wore yesterday to family Bingo: velvet blazer, patterned shirt and black pants. It’s not ridiculously fancy, but I don’t look like a slob either; perfect for a more casual event and trying to keep it classy.

Laid-Back Holiday Dinner

Chiffon Cascade Dress

(Madewell Chiffon Cascade Dress)

I’m into layering, especially when it’s so cold outside. I typically wear dresses like this ensemble from Madewell, layered with a cardigan, tights and boots. This look is nice because again, it isn’t too overdone or understated, and you can wear a dress without feeling frosty.

High Brow Party

Taffeta marvelle mini

(J.Crew Tafetta Marvelle Mini)

I really love the idea of pairing black and navy together because it seems unexpected, and yet done like this with a simple navy skirt and black top + patterned tights it’s still classy (not clash-y). Wear with a sparkly necklace and a vintage clutch in créme, and you’ll look just as boug-y as the rest of the guests–plus this skirt is on sale so it’s definitely a look for less!

Silent Night Slumber Fest

Silk slip dress

(J.Crew Silk Slip Dress)

J’s family often has a “Christmas Morning” event, which entails sleeping over until said morning. I sleep in a dress, so in order to keep things more modest I like to layer a cami underneath–like pictured above–with a cardigan and some high socks + booties. This way I stay warm and comfortable without worry of anyone peeking at my “stocking stuffers” (HA, I’m so witty it’s unbelievable… kidding).

Holiday Brunch

Gingham perfect shirt

(J.Crew Perfect Gingham Shirt–Can you tell I love j.Crew?)

After the aforementioned slumber fest and the gifting that ensues after it, it’s time for holiday brunch. When I’m staying over at someone’s house I like to pack easy to wear ensembles that can still make me look and feel classy even though I’m not at home getting ready. A simple button down and a wool mini skirt + tights equates to effortless; add a patent leather belt over a cardigan and you have warmth PLUS chic.

What Would a Nerd Wear

Of course if you need more classy + simple style inspiration check out What Would a Nerd Wear–Tania has great fashion sense and often serves as inspiration for me!

Happy Holidays!



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