How to Transition Summer Dresses into Fall, aka Google Search: Date Night Outfit, San Francisco


Transition Season Dressing 3  “The coldest winter I ever spent,” Mark Twain once quipped, “was a summer in San Francisco,” and indeed these over-quoted words rang true for the bazillionth time in history on my recent jaunt to San Francisco (sans babes, thank you, Mimi & Papa!) from Denver’s 90 degree + heat.  In SF, Locust trees outside the Powell St. BART stop were starting to turn, the temperature was in the 50s and fall sweaters and boots were in full effect, reminding me that alas, fall is on its way.  Fast forward to the Summer/Fall 2010 transitional season dressing challenge!

After I wrestled the kiddos into bed the night before leaving, I Googled “date night outfit, San Francisco,” and I hit on a number of message board posts about how easy it is to spot tourists in San Francisco: they’re invariably the ones shivering, even mid-summer, in shorts, sandals and/or flimsy dresses with nothing on top.  One sage commenter proclaimed that the key to dressing like a local in San Francisco is easily summed-up in one word: LAYERS.  Okay.  Noted.

My original plan for our night out was to wear a tribal batik-print dress I bought at my fav mall shop, Anthropologie, this spring.  I love this dress.  I wear it every chance I get, from girls night out with sky high-platform sandals and ridiculously large baby-grabber earrings, to barbeques and outdoor concerts with flip flops, and I really wanted to wear it again before summer was out.  My hopes were dashed when I checked the forecast for SF and realized that I, like nearly every other traveler, was perilously close to being mistaken for a tourist.

I called my man-on-the-ground, Hub Dave, who was already in the city attending a conference: “Honey.  I don’t want to look like a doofey mom (and this is the crux of ANMJ, ladies, is it not?  You love being a mom, you just don’t want to look like one) on our romantic getaway.  What are the ladies wearing in the evening?”  Dave: “Um. . . boots.  You should bring some boots.  It’s cold at night here.”  This conversation occurred on Thursday, August 5th.  Me: “Like summer booties or full-on tall fall boots?”  Dave: “I dunno.  Boots.  You know.  Boots.  Tall ones, I guess.”  Helpful.  And insightful, no? 

Packing carry-on, I couldn’t afford mistakes. One pair of packed shoes, two outfits, a few accessories and some mini toiletries.  That’s it.  This would require some serious precision-packing kung-fu.  Armed with the knowledge that my evening-out outfit needed to be layered and include boots (tall ones, I guess), I set about shopping through my closet until inspiration (or psychosis, you be the judge) hit. 

After riffling through my closet and rejecting everything in it as either too summery, too wintery, too casual, too dressy or sooo 2007/pre-first pregnancy, I had an epiphany.  I paired my fav black, white and brown batik print summer dress with a shrunken black wool cardi, a wide black cincher belt and my fab fav cuffed tall boots that have been dying to come out to play since March.  I added a honker cocktail ring, a drapey brass chain bib necklace and gypsy-style gold hoops and called it a day. 

I loved this mode of dressing because after I got out of the "What!? Autumn in August!?!" mentality, a.) I did not freeze my buns off, b.) I did not stick out like a sore thumb, like the chick in a nearly transparent white strapless mini dress with the goose (and other) bumps, and c.) I loved getting the extra miles out of this dress, which I totally adore, and I'm thrilled it will continue to work so well through the cooler months.

To get a few more months out of your favorite summer staples, either choose summer dresses in darker neutral tones, like my batik print, or go for broke: choose a bright floral and contrast it with a dark belt, sweater or jacket and boots.

Transition Summer Dresses to FallFashion Trends & Styles - Polyvore

Transition Summer Dresses to Fall by dynamama featuring Diane von Furstenberg dresses
Diane von furstenberg dresses PINK, 192 GBP
Splendid – Very Light Fashionable Jersey Lapel Cardigan (Black) -…, $93
Ranch Low Cowboy Boot, 83 GBP
High Waist Corseted Ruffle Belt, $138

Gear up a strapless for cooler climes with a turtleneck, tights and oxfords.

Strapless Summer Dress Transition to FallFashion Trends & Styles - Polyvore

Strapless Summer Dress Transition to Fall by dynamama featuring Shoshanna dresses
Sheer Rib Long Sleeve Turtleneck, $28
Nicole "Open Up" heeled oxford in velvet brown, $75

Go cozy chic with shearling lace up boots, your favorite white summer frock, a cardi and a bomber or denim jacket.

Summer Dress Transition to Cozy ChicFashion Trends & Styles - Polyvore

Summer Dress Transition to Cozy Chic by dynamama featuring GAP jackets
Embellished cotton sundress, $96
Fallen Foliage Cardigan, $118
Gap Hooded jean jacket, $70
Winsford Clog Boot, $238

And postpartum moms, layered/transitional dressing is also a great way to stretch your maternity wardrobe out until you've lost some of the baby weight–nothing worse than having a bunch of clothes two sizes bigger than you want to be hanging around when you'll be sliding out of them in a couple of months anyway.  Cinch-up your postpartum belly with a nice wide belt (it'll approximate a waist until you have yours back) over some of your cuter maternity frocks and layer pre-maternity jackets and sweaters (they don't need to close all the way!).  Treat yourself to some hot on-trend shoes (they'll always fit). Voila, say goodbye to post baby wardrobe blues.

– M.




  1. M – Love this post and you look fabulous. Want to come rifle through my closet? You hit the nail on the head. We love being moms, but don’t want to look like one on date night.

  2. Sigh. Am STILL thinking about the cozy boot-with-dress look. How horrible that I’m bummed it’s still 90 degrees? Remind me of this in a few months.

  3. Hi Molly. Very helpful article. Also, makes me nostalgic for SF. I agree that you do look great, and may I say HOT in this well-pulled together (bravo!) date night outfight. I hope you and Dave had a great time. I think that you missed your caling as a stylist.

  4. Great post! I’ve had a lot of fun trying to work with my summer wardrobe, too, to make it transition. One of my favorites has been my swim cover-up (actually a super short, black jersey knit dress from Tarjay) paired with leggings and a boyfriend cardi. I like it with ballet flats now, but tall boots and a scarf will look great when the weather goes down a few more degrees. Still loving your blog!
    ~Jacci in Ohio

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