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

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93 Responses

  1. I LOVE this post! It’s what we ALL go through in choosing an outfit to wear so nice to see that even YOU go through that! Ha! You need to do more of these posts. Loved your thought process for choosing the best outfit, which you ended up doing!

  2. Although I am not a fan of OTK boots, this outfit looks great on you. I like what you decided on the best. (I love ivory sweaters, and I have several.) Thank you for this kind of post; I look forward to more. For work I try to decide on my outfit the night before since we are up and out the door early. But often I try something on, then it just doesn’t feel right. Nice to know even a fashion blogger who is so put together (as you are) has the same problem as “us other folks”.

    1. Hi! Loved this post- more please! I thought it was interesting that you built the outfit around a ‘starter’ piece. And I never thought about taking pics during the process to fine tune. Thanks for the great tips!

    2. I loved this post! And I loved the outfit you ended up wearing, and thought it was the best choice out of all of the options. Thanks for sharing! 

  3. What a great idea for a series! I would not have chosen the pink top. I didn’t like the hemline when it was untucked because it has a rounded hem and the tops of your boots scoop down a little giving the outfit weird horizontal lines. And I didn’t like it tucked in. Had it had a straight hem, I think it would have worked. Though with so much black in the boots, because they’re above the knee, I probably would have gone with darker blue jeans or black jeans. I think the outfit you ended up with was safe– and comfortable. Sometimes we need that kind of outfit and there’s nothing wrong with that!

    1. Interesting observations about the pink top. I thought for sure a lot of people were going to say they liked it better. I love how it looks from that one angle, with my hand in my pocket, but then, I can’t stand like that all night. 😂

  4. I love this series!  This is me when we go out.  I have something in mind and try other stuff until it’s right.  I read somewhere about a 1/3 and 2/3 rule.  Maybe you could talk about that?  Not sure I totally get it but when I’m happy with an outfit it usually fits that.  All of the options were cute!!!

  5. What a fun post to read. And this is why I’ve been following your blog for so long. You keep it real and all of us at some point have had the “evolution of an outfit” experience. In the end I think it came together very nicely and you looked beautiful. The OTK were already a statement item (at least they would have been for me) so I usually keep my other clothing items simple and comfortable. You certainly don’t want to look like you tried too hard 😉

  6. Good Morning Jolynne!! Love this Evolution of an Outfit. Hope you will do it more often. I found myself doing this just last evening. My husband tells me I have too many clothes to go through this. He just doesn’t know me. I have gained a few pounds in the the last year and when one thing fits good and the other doesn’t it’s hard to make it look Good on your body. Anyway, thank you for this blog. I loved what your ending outfit was. Have a Great Weekend and Good Luck with your Dinner this afternoon.
    —– Linda W.

  7. Great series idea!  I have those same thoughts about comfort too & Im glad I’ve realized it’s really important to me to be comfortable & not self conscious.  My problem is I very rarely have a definite starting point or I do but nothing seems to work with it so I change everything get frustrated & then I’m exhausted and have to deal with the pile of no’s, LOL

  8. I really loved reading this post. It’s fun to see that you go through the same process as I do when choosing an outfit. This is so relatable!! You definitely made the right choice, especially with your fur jacket. Hope you had a great night! 

  9. LOVE this post!!! I never knew you went through this! I thought you just owned perfect clothes and everything went together seamlessly. Please do this often, it really helps me see the process as normal. Who knows…maybe it will eliminate some frustration in future!

  10. I loved this post! It was great to see your thought process and clothing choices. I never think to take pictures of my different outfits so I can compare. I definitely need to invest in a full length mirror too!

  11. I really enjoyed this post.  You said that front tucking the sweater is to try hard for real life.  So why do you front tuck so many sweaters in your photos?  I would rather see the outfits the way you would wear them in real life.

    1. Ha, I knew someone was going to ask that. I actually don’t think I tuck many, but when I do, it’s because it seems to look best at the time. When I’m doing outfit photo shoots, I don’t always take the time to go through this process before shooting pix. It’s often me asking Alison, in or out? Okay let’s go! 🙂

      I still like the look of this sweater front-tucked, (although I’ll always think the side view is odd) but I feel silly in it personally – based on where I live and who I am going out with, if that makes sense. I think I’d do it more if I lived closer to Philly, where things are more fashion-forward. That said, I’ve noticed friends out here starting to front-tuck, so it’s catching on. My 14-y/o does it too, and it looks cute on her. I think it looks better on people with smaller chests.

  12. YES!!!!  Please do more posts like this one because it is so helpful, especially with your editorial.  I have started taking selfies of some outfits I put together, which is a huge help in deciding what I am actually going to wear.  And boy, doing that really does help!  I hope that you are able to get everything done early enough today so that you have a few moments to sit before the family begins arriving.  Enjoy the Shane family gathering!

  13. I LOVE this idea! Seems like a lot of extra work for you, but super helpful to know the thought process you are going through to assemble your outfits. The comments on side views are especially helpful — that is often times where I get stuck. I live in a cold climate, so I totally appreciate that you start with the boots and go from there. Pumps in the winter …. no friggin’ way. Sorry, JL mom! 🙂 The fact that you liked the Naadam sweater outfit only after seeing the photos is evidence that we should all be taking pictures of our outfits when time allows.
    Many thanks for the care and energy you put into your blog — and to your family for going along with it all! Happy New Year 2020!!

  14. I enjoyed this post and look forward to more in the future! It not only shows us the “Evolution of an Outfit”, but it gives us ideas we can use when shopping our own closets. Also, I learned several tips to consider from your decision making. Thanks!

  15. Loved the post! My question is would your husband do this? Mine thinks I am crazy, once he puts his outfit on, he wears it no matter how it feels, and I think that is crazy. Glad to see I am not the only one who acts like this when getting dressed!!!

    1. Yeah, men have it so easy. But I will say, there are times my husband questions his outfit combinations, and asks me if things go together. I don’t know that I’ve seen him change and take pix tho, haha!

  16. Love this post! It’s great to actually read about your thought process as you choose an outfit. I change my original choice frequently. Glad I’m not the only one! 

  17. Thank you for doing this series, and yes….please continue it!  I love how you “thought” out your whole process and shared the “whys” and “hows” and also the reasons why it perhaps wouldn’t work.  Shopping our own closets is important for us, too.  Have fun today!

  18. Hahaha so funny ! I do this ALL the time , I actually bought 3 different festive holiday outfits ( reasonably priced) and wore one ! I’m having a gathering at home today and thought about wearing one but went with a casual sweater and jeans because I need to be comfortable and I’m preparing food ! Haha 

  19. Great post!   That fur jacket would make any outfit festive and warm.  So cute.  It is funny how you have an idea, then it just does not look the way your pictured.  It is good to see the process and how you finally decided on which look.  It was a good choice!

    And I’m with your mom ; )

  20. I’m new to your blog and loving it…especially this post! This is absolutely what I go through some evenings. I’m often second guessing myself. Thank goodness I have a patient husband lol. I also loved your comments about the half tuck, calling it a try hard (and the fact that if often looks questionable from the side view. I’m always torn and worry that it looks too staged.

  21. Loved this post because it’s totally ME.  Glad to know I’m not the only one that struggles in this manner.  As usual, you look fabulous.  Pat

  22. Love the Evolution of an outfit!! Also agree with your final choice. That faux fur jacket is beautiful! My second choice would be the leopard sweater and red purse (but understand if it wasn’t warm enough)!

  23. I follow everyday and while I love your blog and your style I don’t comment often, but I wanted to say that I absolutely love this type of post! I agree with the others that this is why we love you. It’s real life! I also go through the same process when getting dressed to go out. I haven’t ever taken pics from different angles, but I think I’ll try that! Thank you for all that you do to put together your posts. Have a great family Christmas today. 

  24. Oh my goodness! Love this post. And I think it would make a great book title.. “Evolution Of An Outfit” by Jolynne Shane… crossing my fingers that you do a book someday soon 😁😉

  25. I loved how you walked us through your thought process! Although the clothing you have is more expensive than I am able to afford, your process is the same! Thank you for being so honest!

  26. I loved this post! It was multiple outfits with multiple opportunities in one post! Often, I have an outfit in mind and I just go with it, not giving myself time to test other options. This reminded me to slow down to try a few outfits. And I love the coat!

  27. I love your new series; such a great idea.  Thanks for keeping it real and sharing all of the “self talk“ with us.  Although I found the form fitting sweater flattering on you I fully understand wanting to be comfortable and not self conscious all evening.  I think you made a great choice and it looked fab with your coat.  

    Your new mudroom cabinets are perfect, BTW.  I’m sure you will love them.  

  28. What a great idea for a post and for future posts!  I too struggle with outfits and have a mountain on “no” pile of clothes on the bed before going out. Glad to know that I am not the only one by the comments.  It helps to follow your problem solving and thinking.  Enjoy the Shane Christmas get together today!

  29. I loved hearing your thoughts on how to choose. Your posts always look so good, it was encouraging to hear it’s a process for you too. And trying on is something I can do.  I don’t think I instinctively know what will go. I also hear you on weather being a major factor.  I bought new black heels I wanted to wear to the nutcracker performance but with the temperatures near 30 I went with boots. I was glad I did!

  30. Haha. I love this post. 🤣 We all need affirmation that we are not alone in trying on several pieces to ultimately assemble the perfect outfit.  To be comfortable, venue appropriate, yadayada. I particularly love the front tuck mental debate. You should have been in my closet Christmas AM debating this very issue with me.  High temps forced me into a blouse vs the planned (and tried on sweater). Argh!  I went with the front tuck and after seeing pics, wished I left it hang. Dang it.  Once again, you’ve nailed a perfect post. 

  31. Oh my Jo-Lynne!! The struggle is real. A real friggen pain 😂🤣 lol!! I love your outfit with the faux fur it really elevates the look!!! I understand about all the dilemmas. Wow I never looked from side angle, I better start checking that out!! I don’t know how to find good stretch otk boots. Never tried them. They look so good over jeans…

    Have a blessed day.


  32. This was a great post! How long did you spend trying all your options?? I wasn’t sold on the outfit until you added the fur jacket….that to me made the outfit!

  33. I wore the pink blouse Christmas Eve and hated it- the buttons would not stay buttoned! I was so uncomfortable and wish I had worn it at home a bit before choosing to wear it.

    1. Interesting! I didn’t wear it long enough to experience the button issue. That’s good to know. I still have the tags on so I will probably return it. I kept it around, thinking it might be “just the thing” at some point, but I really haven’t needed it.

  34. Great post and I love the idea of you doing this again. Your thought process on how you decide what works, and what doesn’t, is clearly articulated and helpful for conveying how you make your final decision (which was the best choice of all you tried!). Thank you for taking the time to walk us through it with you and I look forward to more posts like this one in the new year!

  35. I love that you ended up in the first outfit…I do that a lot!  I also think the front tuck is unrealistic.  Especially sweaters—I can’t imagine who wears them like that IRL.   I like the outfit you ended up in, particularly with the coat (which I liked so much last year that I bought it, too!)

  36. This is a fun post! We ALL do this with outfits. And what’s comfortable for me today may not work at all tomorrow. Often what I picture in my mind doesn’t work at all when I put it on so it’s back to the drawing board, or closet.

    1. Love this post!! And I love the outfit you chose! That coat is my favorite Nsale purchase, so much so that I purchased one for my daughter and one for my daughter-in-law, and they love it! It’s a great piece that appeals to 20 somethings and 50 somethings!

  37. Love this post, and I’m so glad to see that I’m not the only one who  goes through a few iterations 😄
    Your final outfit is perfect! 

  38. This is a fabulous idea for a post.  I love it because it’s just what we all always go through.  I have a problem putting together going out looks like this.  I want to look a little special but like you said with the pink blouse, I get cold when I try to wear my “pretty” going out tops – even if I wear a warm coat, I’m still coat indoors.  I don’t know how people wear sleeveless tops. My arms are always cold in general. I don’t necessarily want to layer a jacket under a warmer coat either. I guess sweaters it is.    I would love more ideas on nice outfits that are still warm.  

  39. These posts are great.. I’m not a fan of otk boots and don’t own a pair… but at the end of the day you looked great and that jacket is gorgeous! At anytime did you consider changing the boots  to something else like a bootie ?

    1. That said, I did consider pumps, but I knew we might have to walk a ways outside, and it was in the 20s that night, and I figured the boots were just as dressy and a lot more practical.

  40. I think you’ve really hit on a unique niche here! I loved looking at the process of putting a look together…and I think it’s relatable for every woman. I love what you ended up wearing (usually I will end up with my first choice, too) and you looked beautiful!  I look forward to more of these types of posts. Merry Christmas!

  41. I really enjoyed the struggle you had. 😀 I thought I was the only one going though this getting dressed. Loved it …made me feel better. 

  42. So great to see you share the process that we ALL go through some days! You looked great in your final choice. I personally loved the gray sweater combo a lot! . Seemed a touch more  “party-ish” bring a little thinner and having the lower cut v-neck. 
    I’m wondering if the length of sweaters and tops will start getting shorter now that we’re all wearing higher rise pants and jeans. I do like the casual look of the front tuck, but agree with you that mire often than not, it looks wonky from the side view. 🥴 I’m ready to start tucking in my entire shirt or top. 

  43. Lol!  It’s nice to know that even you, as a fashion blogger, sometimes struggle with the perfect outfit for an event!  I figured you would have a whole bunch of “go to outfits” for every occasion.  Thanks for keeping it real!

  44. This was my life today…on my way to a baby shower. Needed to take into account the temps for the day, the degree of “casual-ness” vs dressing nice, etc, etc. All the things that end up driving me crazy. The front tuck, I think works for mid day running errands, but not so much for a nicer event. I ALWAYS get tripped up when I get to the shoes. Boy, can they ever make all the difference. Ended up with my first choice also, black knit dress with black tights and black knee high boots. Then heavy on the bracelets.

  45. Agree with all of the other comments  – LOVED this post and so reassuring to know that you go through this as well…especially the front tuck “mental debate”! Please do more of these 🙂

  46. I love this post!  I love seeing your different options and why you decided to “nix” them. I’m glad I’m not the only one who tries on five different things before heading out the door!

  47. Loved this post. It’s kind of nice to know that even a fashion blogger has moments of indecisiveness! I go through this every time I leave the house!

  48. Great post! I am glad I am not the only one who goes through this! I agree with your final outfit decision. It looked great. 

  49. It’s interesting to see how the outfit came together and I think you picked a cosy and comfortable outfit for dinner 🙂

    Hope you had a merry Christmas 🙂 We had a great time with family and so much good food!

  50. I think your final/first choice hit the spot.  The sweater is very pretty and cosy but glam enough for dinner out.  The OTK boots always ramp up an outfit to give a certain ‘je ne sais quoi’.  hope you had a fun evening!
    Best wishes Jane

  51. I love this post!  Real life!  And I really like the outfit you ended up wearing.  Love the sweater untucked and with the coat.  The evolution of an outfit will make a great series.  

  52. I think the outfit you ended up with was the best choice. I wonder, however, why you chose to wear no necklace? To me, this screamed for a long necklace. Maybe your David Yurman piece that you’ve worn before. But the addition of the coat really completed it. I would love to see you do this evolution of an outfit more often! Nice to know us non blogger peeps aren’t the only ones that can’t decide what to wear!

    1. I know it’s kind of plain without the necklace, but I am sort of into that minimalist vibe right now, and I really wanted to wear those earrings. I didn’t have a necklace that didn’t compete with them or look mismatched. (The David Yurman piece is gorgeous, but I wanted a bigger statement, so I went with the earrings instead.)

  53. Thank you for this evolution of an outfit. I go through this all the time and I drive myself crazy!!!! I always wonder if I’m the only one. I’m in agreement, your first choice was the best and I adore your coat.

  54. I love this type of post! I often discard items as I’m getting ready to go out because I just don’t seem to have it right. I’m so glad to see that you do the same. I always enjoy reading your thought processes when creating an outfit. Thank you!

  55. You were right!  It’s fun, informative AND reassuring to see how this all works for you irl.  

    I always think you know JUST the thing to wear, but like any of the rest of us, even though you may have all the pieces…you rethink how they work together.   

    Loved all the choices, but with the coat, that sweater was a beautiful choice!

    Fun post, Jo-Lynne!

  56. I’m so glad I’m not the only one that goes through several reiterations when going out. I like the outfit you settled on. You look so cozy, snuggly in that faux fur. 

  57. I really like the idea of the evolution of an outfit. I found this post very helpful, as it reminded me that I too can take photos to evaluate an outfit. Thanks for doing this 🙂

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