Evolution of an Outfit: Winter Date Night

So here’s a new series I just came up with: Evolution of an Outfit.

You all seemed to like how I showed the various outfits I tried before landing on one to wear to the mall at the end of last week’s daily outfit roundup, so I thought I’d start sharing that process from time to time in a dedicated post.

We went out to dinner last weekend with a group of couples to celebrate my friend’s 40th birthday, and I wanted to wear something casual but also a little special.

Because it was the weekend before Christmas, I wanted to look festive, but I didn’t want to go overboard because it wasn’t a super dressy venue. And one final factor worth noting, it was friggin’ cold outside.

Sorry, Mom! (I’m 47 years old, and she still reprimands me when I say friggin’… haha!)

Normally I build my outfits around my top, but this time I started on the bottom. Because it was cold and I wanted to wear heels, I decided to wear black suede OTK boots over blue jeans.

I often wear black jeans when I go out in the winter, but I went with these medium wash blue jeans to tone down the high heeled boots, and because I like the contrast of black OTK boots on blue jeans.

After that was decided, it was just a matter of choosing a top and accessories.

I had picked up this metallic ribbed sweater with New Year’s Eve in mind, but it also seemed like a good choice for this event.

The metallic shimmer makes it festive, and the open neck is a little sexy for date night, but it’s still casual enough to work for the venue, and it’s a sweater so I’d be warm. It seemed to check all the boxes.

It also looks great with the statement earrings I wanted to wear. (Mine are from last year, but this pair in the crystal color is similar.)

This sweater had been my plan all along, so I threw it on with the jeans and boots and took a few pictures to see how it came together.

It’s okay, but it’s kind of predictable… and the sweater is a little long and bulky.

I questioned if it was too safe.

I tried the front tuck, which is how I styled it when I shared my NYE outfit last week, but front-tucking a sweater always seems so try-hard for real life.

And I think it looks weird from the side…

So I compared it to how it looks untucked from the side, but I don’t love it here either.

You can really see the extra volume from this angle, but then again, it doesn’t look like a bathroom accident either…

I decided to table this sweater and try a few other options before making a final decision.

This pink blouse was my backup plan. It’s been hanging in my closet with tags on for over a month, waiting for just this sort of occasion.

It’s a little dressier than what I typically wear, but I liked the idea of getting out of my sweater rut, and I felt like the jeans kept it casual enough for the venue.

I was a little worried about being cold, but I could wear a warm coat. I have that textured faux fur jacket from the #NSale that I was hoping to wear.

The thing was, once I had it all on together, I wasn’t loving it. While I like the neckline and the color, I’m not sure it’s very flattering.

Left untucked, it seems to add some visual weight on top. Even though it’s not necessarily too long for the overall proportions of the outfit, it just doesn’t have a lot of shape through the waist area.

You can really see what I mean in this front-on shot…

So I tried a front-tuck. This is better, except…

I hate the side view.

The front tuck already looks kind of doofus from the side, but it’s accentuated with this top because the back is already longer than the front. Once you tuck the front, it really looks weird.

Plus, the blouson sleeves seemed a bit much.

I went back and forth and took approximately 162 pictures from different angles, and I finally decided to bag it.

I almost just went back to the ivory sweater, but then I decided to give this leopard sweater a try first. I love leopard and red together, so I added this red bag to the mix.

The fit and proportions are on point, but it’s a lot of leopard. I really prefer this sweater with a black moto jacket on top — both to cover up some of the leopard, and also because this outfit seems to need a completer piece.

But it was too cold for a thin sweater and a leather jacket. I knew I needed a heavier coat, and I just couldn’t get excited about this outfit as-is.

Even if I switched to black jeans, which I would definitely prefer to the blue jeans with this sweater, I knew I’d want that leather jacket to complete the look.

At this point, I was pretty sure I was going back to the metallic ribbed sweater, but I wanted to try one more thing.

This cashmere ribbed scoop sweater had just arrived from Naadam. There’s no doubt that it’s far more luxurious than any of the other options, and the fitted style and scoop neck is more flattering in theory than any of my other options.

But when I tried it on after it arrived, it seemed too tight and low cut for my comfort level. I was actually planning to send it back.

Since nothing else was working out quite the way I’d hoped, I decided to give it another shot with the whole ensemble.

As I’m looking back through these pictures, I am kicking myself for not wearing this. In fact, I ended up wearing this sweater with jeans and pumps to dinner with my family on Christmas Eve.

But in that moment, it felt very tight, and my chest looked very large, and I just didn’t feel comfortable wearing it out with our friends to eat a big dinner.

So after all that, I went back to the original metallic ribbed sweater.

I know, I know… basically, I already showed you the final result in the first look. It’s sort of anticlimactic, isn’t it?

I almost re-wrote the post and waited to the end of this post to share those pictures, but then I decided, this is real life, and sometimes we end up wearing the first thing we tried on.

So yeah, this outfit evolution came full circle!

I have a feeling some of you are going to tell me I should have worn the pink blouse untucked, and maybe you’re right. It’s a more striking outfit.

Or the grey Naadam sweater is gorgeous and form-fitting, so a nice choice for a date night.

But while the outfit I ended up wearing is on the safer side, I felt comfortable and pretty and not at all self-conscious, as I might have in one of the other options, and there’s something to be said for that.

Plus, my faux fur coat was perfect with it.


I hope you liked this first evolution of an outfit post. You’ll have to let me know if you’d like me to do more of these.

Enjoy the rest of your weekend!

For the Pinners…

Evolution of an Outfit: Winter Date Night

Did you like this post? 

Subscribe to get email updates! In addition to my most recent blog posts, you’ll receive exclusive newsletter content like special sales, my newest favorite finds, and an occasional peek behind the scenes — all delivered right to your inbox. PLUS you’ll be automatically entered for a chance to win a $100 gift card each month!

This post contains affiliate links. When you shop through my links, it helps support my business (at no additional cost to you) so thank you!