Season Changes and Fashion Struggles

Dear Gabby,

It is officially the awkward transition from summer into fall season and some of the hardest weather to dress for.  On weekdays, I walk to work and in the summer I wear flip-flops to walk and in the winter I wear boots, but right now I am stuck on every aspect of what to wear.  As for shoes, it is too cold in the mornings to walk in sandals and way too warm to bring out the boots.  I don’t want to walk to work in my nikes, but what is the best in between shoe do you think?

As for outfit options, both work and weekend clothes, what outfit is a happy medium?  In the morning it is cold so I feel like I should be wearing layers or a jacket but by time it becomes a little later in the day it is way too warm for any of that.  

What do you suggest as a perfect go to work outfit and a go to weekend outfit during this awkward season?


The girl who is stuck in a fashion crisis


Dear the Girl who is stuck in a fashion crisis,

Girlfriend, I know, the struggle is real this time of year!  The transition from summer to fall can sure be challenging but it can also be fun!  Keep reading and lets explore three options I think you will like that can carry you from workday to weekend! 

Time to retire the flip flops and bring on the open toe booties, flats, and sneakers.  I know you mentioned you didn't want to walk to work in your Nikes, but hear me out.  A sneaker with a work outfit is very 'on trend' right now.  I was catching up on some of my fashion reading today and noticed splashed all over so many pages were models with their pencil skirts in their Converse sneakers.  Looks better than it sounds, but make it even edgier and pair your look with a moto jacket to keep you warm in the morning when it's cool.  

Another option is of course is a flat.  From the sounds of it, it seems like you walk quite a distance so I recommend a loafer over a ballet flat.  They're much more comfortable and offer you better support.  Your feet will thank you!  Here I would pair your loafer with either a classic blazer for more of a preppy look or you could off set it with a 'boyfriend' cardigan and your favorite specs.  Think JCrew meets 'street style'.  

Lastly, one of my favorite shoes to bust out this time of year, is the open toe bootie!  Full of comfort, style, and perfect for this transition!  Try to get one with a chunky and/or low heel (they will be more comfortable).  I love to pair my booties with a cape.  It's classy, easy. and looks great!  Throw that on in the morning and in the afternoon you can fold it up and throw it in your tote bag when it gets warmer out.  

And speaking of a tote bag!  This accessory will also be very essential this time of year.  Since we're adjusting to the next season wearing layers is a must!  A stylish tote is great for stashing your cape, jacket, or sweater for when you need to add or shed a layer.  Also, if you want to swap out your comfortable walking shoes for heels this is where the tote bag comes in handy!  Think of it as a mini extension of your closet or what I like to call it, my "Marry Poppins bag of stylish tricks'