While summer and holidays are the more popular choice for traveling, there is still something to be said for taking advantage of the cooler weather and less crowded destinations in the fall.  I (Jen) have always had this dream of traveling up the California coast by train and stopping in tiny seaside cities along the way. In my fantasy, this vision is complete with monogrammed Louis Vuitton steamer trunks, each filled with perfect ensembles, glamorous accessories and shoes for all occasions. Back in the real world, though, our fall trip will probably be more of a weekend in southern California (perhaps Santa Barbara?!) and the packing will be much more low maintenance…         

When it comes to dressing for the fall, start with something lightweight like this polka dot silk dress.  Since the weather tends to vary greatly from day to night during these transitional seasons, continue by adding layers that you can shed as the temperature climbs.  I wear black opaque tights really often during the fall and winter and have test run quite a few pairs.  My absolute favorites are these tights by Wolford. They are super opaque which makes them very flattering on your legs.  The cheaper alternatives I’ve tried tend to be really sheer and run easily.

My second layer is this trench coat which is perfect for a misty day.  You can also top off your fall dress look with a longer style cardigan or blazer.  Here’s a tip: Pay attention to the waistline of the dress when choosing a layering piece.  This dress has a long drop waist so the longer style trench works perfect.  A cropped blazer, on the other hand, would look a little funny with my look but is perfect for a fifties style dress that hits at your natural waist.

Now on to the shoes.  I was styling a photo shoot this week when I encountered someone who still thought that you couldn’t mix black and brown within the same outfit.  Luckily that thinking was thrown out decades ago when people stopped matching their shoes to their handbags. Black with brown is not only perfectly acceptable, but one of the most chic color combinations if you ask me.  I chose brown wedge boots with this look to make it a little more casual.

 Anyone out there taking a vacation this fall?  Happy travels… and packing!

Rag & Bone trench coat (similar); delicate rings from by boe; green ring from Forever 21 (similar); necklace from Target (similar); boots form Marc by Marc Jacobs (similar); tights from Wolford; Dress by Sandro (similar)

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