What I Wore/How I Styled It: Rainy Day Wherein I Fail at Button Downs Under Sweaters

This is what I wore to church yesterday.  Can you tell it was a rainy day?  (Hence the indoor photos and strong overhead light.)

Plaid button down by Japna – thrifted
Blue sweater by Loft – thrifted
Blazer by Cartonnier – thrifted
Cream corduroys by Lauren by Ralph Lauren – thrifted new with tags, then tailored from a wide leg to a slim leg
Rain boots – thrifted, no label

I was, in theory, happy with this outfit.  I started it out (in my head) with these rain boots, knowing I would be corralling a small person in mucky, wet weather:

This is the closest I own to riding boots.  Ha.

I wanted to pick up the pink, the light blue, and the dark navy, and this button down and sweater did the trick:


My pink/blue marled Cartonnier blazer was the obvious topper.  (And I thought I wouldn’t get a chance to wear it this season – because these ain’t exactly wintry hues.)  Close up on the colors/patterns:


The cream corduroys provided some nice neutral real estate between all the color and pattern on top and in the boots.  Navy pants would have worked, too.


So here’s the problem: in theory, I love the idea of a button down underneath a sweater.  It seems so chic – little pops of pattern at the cuffs, neckline, and hem to contrast with a solid (or even not-so-solid) swath of sweater.  And the warmth!

But in reality, this pairing drives me nuts.  The button down never lays properly under the sweater (see all pics above except the first one, which I made my spouse retake for the sake of my vanity).  It looks lumpy and pointy and things pop out in unfortunate places. And even though this plaid shirt is decently long, I’m forever tugging at the hem to make sure it’s peeking sufficiently chic-ly below the sweater.

In short, this combination looks chic on Talbots models and in my head, but NOT on me.  Even this combo had to be pulled and adjusted all day, and flattened for this photo (and some button or other pointy part still looks mysteriously like an errant nipple):


A photo posted by LeahLW (@thriftshopchic) on


Enlighten me, readers!  There have to be some of you out there who wear this look with aplomb and nary a stray scrunch.  What’s your secret?  Is my sweater too thin (it’s a thin cotton knit)?  Do I need to wash and dry it to shrink it up a bit or iron it before each wearing to get that smooth look?  Is my button down shirt not long enough or form-fitting enough?  Do you secretly safety pin or tape the whole thing in place??


Scroll down to comment – and don’t be afraid to wear rain boots as legit footwear, especially since there are so many fun patterns and chic styles to be found in the thrift store:

A photo posted by LeahLW (@thriftshopchic) on


A photo posted by LeahLW (@thriftshopchic) on


A photo posted by LeahLW (@thriftshopchic) on


A photo posted by LeahLW (@thriftshopchic) on



7 thoughts on “What I Wore/How I Styled It: Rainy Day Wherein I Fail at Button Downs Under Sweaters

  1. Love the BOOTS! Yesterday was the perfect day for those boots in Upstate South Carolina too! About the sweater/button-down combo: when I’ve tried this the shirt (if too stiff) always seems to look crumply under a too-thin sweater – perhaps a thicker sweater would corral that shirt into submission . . . but if the shirt is too silky it crushes and looks droopy under the sweater . . . Keep on trying, Leah!

    1. Thanks for the tips, Carol! Note to self: try a not-too-stiff, not-too-silky shirt plus a thicker sweater. (Now I just have to find both of those!)

  2. Hi,
    I have totally given up on layering- some people pull it off effortlessly but I sure can’t! The closest I’ve come is by wearing a thin, like chiffon thin, form fitting under layer then a heavier sweater on top. The under layer has to be thin, smooth enough to lay flat. But- it still makes me crazy uncomfortable and I tug all day. Thanks for the post- I don’t usually comment but want you to know I appreciate your blog/point of view especially your insights on the disenfranchised among us.

    1. Tonia, as these recent fails show, I’m in the same boat – I have a couple of skin-tight sleeveless shells that go underneath lightweight sweaters, but they’re totally functional and don’t show above/below the sweater.
      So glad you commented and that you appreciate the blog – I love thrifting and love using it as a way to address social/justice issues.

  3. I don’t even try the blouse under sweaters look either. Same problem. I have even tried the silky blouse idea and it does not have enough substance to stay out at the hem to show. Still bunches up! Constantly tugging at it. Makes me crazy. I just want to be dresses and done. So I don’t even attempt it anymore. The models and mannequins aren’t moving around as in real life. I gave up

    1. Jill – SO TRUE. Do you think they tape/safety pin/otherwise secure those shirts underneath sweaters for catalog shoots?? As a matter of fact, I guess *I* could do that… but I think my laziness will win out over wanting to mix fun prints, because as you say “I just to be dressed and done.” Thanks for commenting!

  4. Hi Leah, I would echo the commentary above that you need to have a thin and not stiff button shirt underneath. I really like JCrew’s button shirt called the “perfect shirt” for layering under a sweater. I tried it with a thin Merino sweater a month ago, and it worked really well. I’ve also seen on Pinterest the suggestion to wear a tank top over the button shirt before putting on the sweater. I haven’t tried this yet. (Btw, I never replied to a comment you responded to me a while ago about the Stylebook app but I have been thinking about it. I took the plunge to try the app but was sorely disappointed to find out I couldn’t. Stylebook is only available for Apple and I have an Android, but I did try out a few similar apps and have found that it does help me see what I own, which has made me want to buy fewer clothes, and select outfits in advance, which takes some stress out of the morning rush. I may write that guest post during my time off in the next few weeks.) Anyway, thank you for being diligent in writing your posts as I always enjoy reading them.

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