Fabulous Fall: Transitioning Your Wardrobe

Today the lovely Lilly Lemontree gives us sage advice as to how to best transition our wardrobes seamlessly from summer to fall. Since Fall weather is so unpredictable, we often need to create new rules and although we may be ready to pack up and put away our summer clothes, temperatures often won't allow us to do so. My Los Angeles friends are experiencing temperatures in the 100s. Cashmere cardigans are not even in their thoughts. Meanwhile, here in New England we may wake up to temperatures in the 50s and see them climb well into the 70s or 80s by lunchtime. Below, Lilly Lemontree gives us currant, stylish advice as to how to stylishly dress the part.


I have always loved the fall and the month of September in particular (Now, now, summer, don’t go getting all offended. You are still quite dear to me and if you happen to talk to me around February, you will find me waiting for your return with bated breath but after what seems like months and months of hot temperatures and sticky humidity, the first few weeks of September seem like a breath of fresh air). As of late though, I have been known to refer to it as a month of confusion. You may be asking “what’s to be confused about, Lily?? The little tykes are all safely back in school (was that a sigh of relief we all just heard?? I swear it wasn’t me!) and the adults have gotten back to business and a little more order.”

Well dear friends, the confusion unfortunately lies in the flip-floppy weather that I have been told we have global warming to thank for and in turn, the daily game of ‘what should I wear’ turns into an Olympic competition of sorts. I am convinced of this every time I go to pick up my children afterschool, run to the market or meet up with friends for a cup of coffee. For example, yesterday while standing outside waiting for my children to be let out, I stood behind two moms who were chatting. One was dressed in a tank top, short capris and sandals while the other had chosen a thick, hooded sweater, wool pants and knee high boots. As I stood behind them, I thought about what an odd looking couple these two ladies made but as I started to look around the schoolyard, I noticed quite a few individuals who if mapped out based on their attire, represented all the climate zones in North and South America. 

Difficult as it may seem at this time of the year to predict the weather, it is really quite simple to transition your wardrobe from one season to another with a few easy steps, five to be exact! (I’ll insert my most appreciative ‘thank you’ to our wonderful hostess here at The Entertaining House who has allowed me an open platform to offer my ‘sage advice’, which keeps me from counselling total strangers on the street and running the risk of being hauled away in a police car. Thank you EntertainingMom for keeping me out of the clink!)

1) Switch out your shoes:

Back to the depths of the closet go all your sandals, flip flops and anything that exposes your little toes. Ditto for anything white. (Since you are giving all your summery favorites their walking papers for the season, give them a wipe with a soft cloth, checking for any stains that might settle while they hibernate and take anything that needs a little more TLC to your local shoe repair or cobbler to be properly cleaned and repaired)
Shoes you can keep out? All the lovely ballet flats and closed-toed kitten heels that have been all the rage this summer.

 Bring forth the loafers in caramel shades, ankle boots in cafe hues and oxfords with stacked heels.



2) Divide and conquer by material.

Much like all your white clothing and footwear, there are a few fabrics that denote summer and summer only. Send packing anything made of linen, seersucker, madras and gauzy, tissue-weight cotton. Most other materials can be kept around for awhile and by the end of the month, you might even pull out the corduroy and mid-weight wools.

3) Most of us think we have to tuck away anything strappy or sleeveless come Labor Day but with the help of an array of covers you can get a little more time with any of your favorites! Keep all your tanks, shells and cap sleeve tops in rotation by throwing on a hot fall trend like a boyfriend blazer or turn to a classic like a pashmina scarf, lightweight cardigan or denim jacket to finish your outfit. Some chilly mornings can turn on a dime and blossom into a warm and sunny afternoon, in which case you lose the topper completely or show your ‘true prep’ and tie your cardi around your shoulders! This works vice-versa as well, since we all know that the sunny blue sky that guided us to work in the morning can turn an ugly and downright frosty grey as we head home. Throw on that topper and keep your goose bumps at bay!

Ruffled Cardigan from Talbots

Gwyneth in her boyfriend blazer and cropped pants

4) Let pant hems ‘fall’ south, south of the mid calf that is! While mid-calf and ankle length cropped pants are perfectly acceptable and downright trendy at this time of the year, it is time to banish any pant that lands above that. Not sure what region to stay away from? Stretch out your hand, place your thumb at the bottom of the knee cap and lay your outstretched hand across your calf. That cute little pinky of yours marks your border, anything below that last digit is free game!

Mid-calf cropped denim at Talbots

Rachel Zoe sporting her crops

5) Accessories are your last line of defence (so to speak) when it comes to transitioning into fall! Gone are the beachy totes and straw bags and in come pocketbooks, purses and satchels in animal print (faux for those of us that care to be kind to the little lizards and crocs) and heavier skins (leather and suede). Also on trend once again are the abundant scarves and wraps that can be layered on or whipped off in a wink!

Lizard satchel at Brooks Brothers

Julia Roberts and her chic scarf

Since I have shared my ‘secrets’, it’s time to share yours!
How do you transition your wardrobe from stylish summer to fashionable fall??