More Style Mishaps + What I Wore Sunday

This is what I wore today:


But actually I kept my coat on all through Mass, so the overall look was more like this:


Which reminds me: I have a tough time figuring out outerwear.  Growing up in Florida, a coat was something I needed only a few weeks out of the year.  I never thought of it as part of my outfit, just something to throw on to keep warm, like a blanket.

Fast forward to first year of law school, and I’m wearing a red, bulky Lands’ End parka with my black skirt suits.  Not the cute, quilted, fitted parkas I see around nowadays.  Just big, bulky, functional.  Fortunately, I caught on and bought myself a dressy wool overcoat (still red!) before I entered the working world.

Okay, so fast forward some more to a few weeks ago.   I went to a Christmas concert with a friend, and the night was cold and rainy.  I got it stuck in my head that I had to wear the trench/ rain coat, and not my standard wool overcoat.  But, I was afraid I would be too cold in just the trench plus my standard church/ dressy uniform of pencil skirt + cardigan/ sweater.  (Plus most of my sweaters are showing their age, and they seemed a bit shabby to wear to the concert).

So, I wore this:


but also put on this my new-to-me blazer, over the sweater and under the raincoat.

This blazer has an identity issue.  Worn with navy, it looks black (as in this outfit from a few weeks ago):

Ralph Lauren blazer infinity scarf pencil skirt brown boots

But worn with black, it is definitely, definitely navy.  I didn’t realize this until I already was at the concert, looking like a color blind Hogwarts dropout:


I was going for something like this:

But I think my look was more:


And I don’t like the logo thingy on the pocket, anyway.  So this thing is going up on Ebay.  (Maybe it will find a nice Catholic owner who will take its newly-converted self to Mass every week?  😉

The whole experience left me yearning after a dress, something that (a) is long sleeved and warm, (b) is dressy enough to wear to church, concerts, parties, etc., but (c) is casual enough to wear with flat boots, and (d) doesn’t cost anything.  Ha!  So, yeah, I’ve been doing a lot of browsing online:

Links available here.

Links available here.

Probably the most frugal/ versatile thing to do is buy a non-shabby sweater.  But part of me just wants a new dress.

But even a warm dress might not be warm enough with just a trench coat.  I can’t figure out how to do outwear.  I just don’t get it.

What about you?  What’s your go-to outfit when it’s wet and cold but you still need to dress up?  Do you prefer dresses or separates?

Linking up with FL&P today.

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17 thoughts on “More Style Mishaps + What I Wore Sunday

  1. Oh, your outfit for Mass was beautiful, and I love your coat. (I kept mine on through the whole thing as well. It’s COLD outside). I’m actually here realizing I’ve been to your blog before! When I decided to go “minimalist” with my wardrobe. It’s been so much happier around here since, so thanks!

  2. I struggle with outerwear too, I think because I just moved after spending 3 years in FL where you rarely need anything warmer than a sweater. I think you just need an in between coat…something between the trenchcoat and the wool coat. Maybe a nice leather jacket? ThredUp really does have an awesome variety and great prices.

  3. Winter dressing in general is hard for me. l am always cold, so I tend to dress more frumpy just to stay warm.
    But, when l have to dress up in the winter l like to wear dresses with cardigans and dressy scarves.The problem is, l dont really like the look on me of long boots with skirts /dresses, it just looks like too many start-stops of articles of clothing if that makes sense. So l prefer to only wear dress shoes with skirts / dresses and keep my boots for over jeans with a longish shirt. The result is that I don’t dress up (dresses and skirts) much in the winter-even for Mass- shame on me!

  4. Dresses with long sleeves are an endangered species!

    I can never keep my coat on inside. It gives the impression of not staying long, so there’s no need to remove layers, which just seems wrong for Mass. I am very sensitive to cold, though, so I am all about sweaters/cardigans. If I’m cold, that’s better for staying focused and awake anyway.

    For me, outerwear is about a layer of wind-blocking against the cold. Once I’m inside, where there’s no more wind, I don’t need that layer anymore. YMMV.

  5. When I first moved from the west coast to the Midwest I also had a hard time figuring out outerwear. Thankfully I found several nice wool coats on sale prior to my big move. Personally I would advise something like that from Jcrew or Banana Republic but wait until the spring and summer lines come out and you should be able to find one majorly discounted. I still have my jcrew wool peacoat that I bought eight years ago. It’s such good quality it still looks brand new and it’s more classic than trendy so it should last me for many more years. I think I payed around $100 for it which isn’t bad considering I’ve had it so long and I wear it every winter. Also make sure you get a neutral color so you don’t have to worry about it clashing with your outfits. One of the first coats I bought was bright pink, it didn’t last me long because it didn’t go with anything.

  6. I love your mass outfit, Laura! I prefer skirts and sweaters when dressing up in the winter- but I’ve also never considered looking for a warm, long sleeved dress. Hope you find something! And I have a hard time dressing up my blazer, too, since it’s such a dark shade of navy. For what it’s worth I think yours looks great in both looks. 🙂

  7. The HP reference made me laugh! Growing up in the Mid West it never occurred to me that everyone doesn’t have a LOT of coats. We have to have coats for all types of weather, even my kids have a least 3 coats–church coats, coats to play in the snow and rain. A really great blog that covers cold weather fashion is

  8. Born and raised in upstate NY, I know cold! If its cold and rainy add warm layers, like a wool vest or scarf, gloves, and a hat. But if you aren’t going to be standing outside, I would wear the wool coat. Wool naturally wicks water so you won’t get soaked. If you are going to be outside in the rain, I would put a fleece on under the coat, then, when you take off the coat just take the fleece off with it so you will still be dressy but not freezing. And when all else fails, drink something either hot or that will make you hot!! Lol

  9. Laura I love love love that coat you got me for Christmas back when F1 was born and it is so very warm. It has that thinsulate lining which is both thin so not bulky but also ridiculously warm. Seriously. I’m so cold blooded that I NEED warmth. Also consider if you bought a dress also buying a silk slip. I have silk long johns from lands end and once again they’re not bulky and so smooth and thin and boy do they keep me toasty. I’m sure if you would I get a slip to wear under a long sleeve dress and had a thinsulate lined coat you’d be surprised how warm you were.

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