The Three Fall Transition Outfits I Can’t Stop Wearing


We had a fabulous Labor Day weekend.  Saturday, we went to the shore (natch) and on Sunday?  It rained.  I mean the heavens opened and it poured.  Great, big, fat, sopping-wet raindrops.  And we loved it.  We splashed in puddles (Pax rolled in them) and then we all came inside for hot chocolate and pancakes.  A perfect way to welcome September.

Raines starts pre-school week after next, and already my mind is turning to cool nights, crunching leaves and that slightly smokey smell of Fall air.  Ooooo….so excited.

However, the temps are staying firmly in the 80's over here.  With cah-razy humidity.  So here's what I've been wearing to satisfy my Fall cravings, without drowning in sweat.  

Swap Cut-Offs For Cold-Weather Shorts, Add Booties

You know I love my cut-offs.  But on days when I'm really craving Fall, I swap 'em out for something more substantial.  Personally, I love faux-leather (mine were $15 from Forever 21), but a cool tweed short would also work.  Add ankle boots for a perfect early-Fall pairing.

My boys have suddenly turned crazytown.  They never, EVER, stop.

(wearing: tee from Anthropologie, faux-leather shorts from Forever 21, Clarks booties – similar here, fringe bag from Piperlime – similar here)


Try Lightweight Scarves + Strapless Necklines

Wear a strapless sundress during the 80 degree days, then bust out a lightweight scarf for happy hours at the beer garden.  Man, we're going to be sad when Morgan's Pier closes for the season.


(wearing: DVF strapless dress, Echo designs scarf, Salt sunnies)

 You gotta love a place where you can order grilled broccoli and corn-on-the-cob for the kids (for, uh, $3?) and where this kind of behaviour is totally acceptable:



We heart iPads for happy hour.  It's OK – you can judge.  We have too much fun to care.  (Besides, I know no one is really judging.  Us Mamas are a supportive bunch.)  


Flannel Shirts + White Pants

I kinda love this pairing.  It works best for cool summer nights.  A cozy plaid, sleeves rolled, with white pants and heels.   


(wearing: J.Crew perfect flannel shirt and heels – another awesome plaid and similar shoes, KUT From the Kloth white denim c/o Shop Adornsimilar here, vintage clutch, Lindsay Bloom cocktail ring)


Mamas, what are you wearing to welcome in Fall?  Spill!  A gal can never have too much inspiration…




  1. Thin, gauzy dress (best for over beach wear) in a fall color (olive green) with short boots and brown tights and a jean jacket… it’s kinda chilly over here in Germany. Plus the dress is loose-fitting and hides my post-partum pooch!

  2. Maternity skinnies, sandals, ribbed tank and a light scarf…36 weeks and counting down! Cannot wait for cooler weather and some cute non-maternity sweaters! LOVE the flannel with white outfit. I don’t think the labor day rule applies anymore.

  3. Love the flannel & white jeans. I’m so happy flannel is back…in a more glamourous way than the grunge of my college years! And no judgement here. We love the ipad here! My 3year old is obsessed with “Monster Socks”!

  4. Love the strapless dress and scarf combo and the white jeans and flannel outfit. And I know it’s silly, but whenever I see leather shorts (or fake leather shorts) I think that my hooha would totally be hot.
    My ‘go to’ fall outfit is jeans, slip on chuck taylors, a t-shirt (usually from Lucky) and a fun super fluffy and pretty colored scarf. =)

  5. Question: Where do you put the kids cups in some of these bags you carry? You do just throw them in there and hope they don’t make a mess and leak? I usually have to have bags with an outside side pocket for my daughter’s cups. ??

  6. I’m sort of sad that I’m pregnant and can’t fit into my tweed shorts from last winter. But definitely on the hunt for some well fitting maternity skinnies. My pair from last time are humongous.

  7. Thanks, Mamas! Love the ideas! Kate – I always associate the thin, gauzy dresses with summer….but man, in a darker color, they would be pretty darn perfect!
    Karen – It’s an old rule. You can totally wear white all year long. ๐Ÿ™‚
    NW – I hate kid’s cups. I’m always losing a lid here, or forgetting to wash them, or UGH. I don’t buy them. I do glass at home (I use jam jars – they are virtually unbreakable) and out & about I just do water in kid Sigg bottles. The caps are leak-proof enough if they are on tight, so I just throw them in my bags with everything else.

  8. I LOVE your blog. Love, love, love it. My wardrobe is better because of you, thank you! My fav fall outfit is sweater dresses and tights.

  9. I’m 7 months preggo and I had some summer tunic style dresses that I’ve started pairing with leggings. I’m not normally a leggings girl but, I’m into comfort at this point. I also have some maxi skirts I’ve been wearing with my tank tops and layering a jacket or cardi on top. I’ve decided I need to purchase a pair of maternity jeans, my bella band is no longer working for my “normal” jeans. Any ideas of a good (affordable) brand? I’d like some skinnies. ๐Ÿ™‚

  10. Thanks for the info on the cups! I’ve found the Playtex sippies to not leak, but they are about the only ones! I guess I could just throw them in. I’ve been meaning to try Sigg or Klean Kanteen, so maybe I’ll do that….it would definitely broaden my options for mom bags. By the way, love these looks! I’ll definitely be wearing my white jeans with my plaid shirt and Toms as soon as we get fall here in Vegas, and I love the scarf with strapless idea. I’m so glad I came across your blog-am currently obsessed and it has been life changing! I’ve been thinking about trying the Style Mint T’s. How is the sizing? I’m typically an XS/S in tops, Medium some times if I want to size up unless the shoulders are too broad. Also wondering about those Levi leggings and how they run??? Usually a size 0 or 2 in pants, but I’ve got the post partum pooch too so junior sizing scares me! Thanks!!

  11. Hi! I love all these outfits! We are planning a trip to Disneyland for October and I just discovered that it is going to be much warmer than I was imagining! No skinny jeans and boots for me. I will be honest and admit that I get incredibly cranky when I am hot and sweaty, but I get cold really fast too. I was wondering – in these transition months when it is cold in the am and then 80 in the pm, is it still okay to wear footless tights under a skirt or dress and then take them off when it gets hot? Just curious! Thanks!

  12. I have a cute pair of white maternity crop pants (Gap clearance racks for $2.97, no joke)and I LOVE the idea of pairing them with plaid to make them look more fallish! It’s been so hot all summer I’ve only worn them a few times-been mostly sticking to shorts and short dresses!

  13. BusyBride – have you seen the sweater dresses at Old Navy? Crazy cute and so cheap! I might try the leopard print…
    @Gina, my fav maternity skinnies are from J.Brand (check ebay). Otherwise…I was pretty happy with Gap, actually.
    @NW – Junior sizing scares me, too! I went with a 1 in the Levis…although there was barely any difference between the 1 and the 2. You could size up initially. In Stylemint, I typically go 2. Simple because I like those shirts to fit a tad big.
    @Jenny – Sure you can! Personally, I love layering leggings under dresses with ankle boots. It looks more finished than flats. And ankle boots + dresses look awesome with bare legs.

  14. S — I also have to admit that I found your comment “It’s OK – you can judge. We have too much fun to care” super refreshing! I’m going to repeat it to myself it next time I see anyone judging! ๐Ÿ™‚

  15. It is still too hot, but I’m excited to wear my light grayish-brown, short sleeve sweater dress (that I have been trying to think of ways to style) layered over my teal, sleeveless maxi dress (like you did with some dresses in an earlier post). I tried it on today and will definitely do it- once the temperature drops. :-D. Thanks for the inspiration!

  16. I love the strapless with scarf combo. Did that a lot a few years ago when my son was born in late August. Wonderful transitional outfit. Add a cardi, jean jacket or cozy sweater and you’re good on chilly nights.

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