How To Wear Plaid Part 3: Date Night


I love the idea of a plaid shirt for date night.  The casual nature of plaid lends itself well to an overall effortless BLAH BLAH BLAH.

Really, I just like to be comfortable.  You too?  Good.  Keep reading.

My first thought was to tuck the plaid into a high-waisted pencil skirt.

[I don’t have one of these.]

Soooo…I just hiked my standby black pencil skirt up near my boobs and added a thick belt.  Which I then tugged down a bit so ‘the girls’ weren’t actually resting on the belt.

Which was brown.

[But…ummm…OK.  Can still make this work.]

Then added olive green tights and cognac boots to tie into the brown…and voila!


A cool outfit that [bonus!] goes nicely with the dead plants on my balcony.

This combo, however, is terrible for the post-partum pooch.  Observe.


Ouch.  So….non-post-partum moms, go nuts.  For the rest of us…

Shorts!  [Please.  No rolling of eyes.  You knew I would bust these out again.]

Yes, I’m still on a shorts kick.  But lotsa leg is a nice distraction from the post-partum pooch area.  Or so I’m thinkin’.

While this look would work with a regular plaid shirt, I probably wouldn’t pair a very casual flannel plaid shirt with dressy shorts. But the print and fabric are key. (Thinner, drapier plaid will work better than a thick flannel.)

If the lacy tights are a bit too racy (or cold)…try layering them over an opaque tight in another color (I’ve worn these over burgundy tights).

I’m wearing my Banana Republic plaid shirt (also seen here), Flexees shaper cami, Forever 21 faux leather shorts (similar here), Wolford tights (similar here) and J.Crew heels.

Incidentally, do you remember those annoying Secret (deodorant) commercials a while back?  Where some chick would stare into the camera and say provocatively, “I have a secret.”  Then she’d toss her hair, look around, giggle, then whisper into the camera, “I’m afraid of the dark”, or some other inane thing?  Yes?  Well.

I have a secret.




My milk?  [tosses hair]  It just came in.  And my shaper cami? [giggle]  Now drenched and stained. But thanks to my slightly oversized, dark and ruffled plaid shirt, this will remain my secret.

How do you spell “new mom”?  H – O – T.  Yeah, baby.  Just don’t touch my shirt.

[Amazing, really, that milk let-down thing.  I just happened to think about the little one as I walked down the stairs…and BAM.  Wow.]





  1. I’m dying of laughter right now! You are too funny. You have be wanting (obsessing) over getting a pair of shorts. I want jean cut off shorts AND thin black ones. And by the way, I haven’t owned a pair of shorts since 9th grade. Now, if I can just get H to cooperate in the dressing room AND find somewhere to wear them too. 🙂 thanks for the chuckles!

  2. 1st photo: your hands got chopped off! Oh no!
    2nd photo: you are awesome for showcasing the pooch, because in all of your posts, I’ve yet to believe you actually have any pooch.
    Shorts + Tights + Chicago winter = totally a no go for me.
    You look cute, but I would just feel ridiculous, even if you could convince me that it’s just as warm as a skirt and tights in the winter. Mental block on my part I suppose, but then again, I hardly even muster skirts in the winter!

  3. I love this post! I don’t like it when people say “LOL” because somehow I always doubt that they are actually laughing out loud. But, I can say that today, you made me LOL! :). Oh yeah, the outfits are cute too!

  4. Fun stuff 🙂 You look awesome, pooch or no pooch. I’m seriously thinking olive green tights need to come find me. I’m really into olive/navy/charcoal-with-a-bit-of-brown combos this winter, and olive tights would be perfect with a few things I already own!
    I wonder what your date night shorts would have looked like with the olive tights and brown boots (?).
    You’re looking great!!!
    ~Jacci in Ohio

  5. If I had gams like that, I’d be rockin shorts in the winter too. Alas….I could never pull this look off. Still love your plaid shirt though 🙂

  6. Nell – it’s funny, but shorts-in-winter got me back on the shorts kick again also..,
    Lisa – thanks for writing in! Yeah – fun is ONE word to describe it…
    Amy – of course it did! Lol
    Kate – where ARE my hands??? So weird! But yeah – Chicago is some SERIOUS cold. I wouldn’t even mess with skirts, to be honest!

  7. Grace – I am a terrible lol offender. Mostly I’m just giggling to myself. Ok, sometimes snorting. But still. Am so glad you lol’d.
    Teagan – thanks, chick. 🙂
    Jacci – hmmmm…good call. I like my olive tights and tall boots with just about everything….
    TJ – thanks!!!

  8. What brought ME back into the shorts kick?? The fact that you can wear them with TIGHTS. Unlike you, lovely cellulite-free sister, I have to deal with the unfortunate reality of cellulite. Not pretty with a pair of sexy short-shorts. HOWEVER, upon discovering the joy of pairing opaque tights with shorts, I bought them to my heart’s content. I even wore a pair of sequined shorts for New Year’s with black tights underneath and got lots of compliments . . . cellulite, hidden. 🙂

  9. Yes. Well. After two kids, I’m no longer cellulite-free. But I keep thinking I am….until I catch sight of the rear-view in the mirror and think, “what the h@ll??????”
    BTW – you looked crazy-hot NYE. 🙂

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