I received an email from a reader who posed a great question to me.  She wanted to know what to wear on an upcoming girls trip.  As she wrote in her email:

How does one have fun with clothing and not look ridiculous?  I’m very out of practice with dressing for these sorts of occasions (and frankly was never that great to begin with).  We’ll be tooling around town, seeing live music, and hitting a few bars (gasp!).  I searched your site for “girls trip” and didn’t get any hits.  The followers of your blog who have children are finally to a point in our lives where the kids can more easily be left with caregivers…so bring on this girls trips!

Not being a parent, I can only imagine the liberation felt when a mom can leave her children for a few days and hit the road with her girlfriends.  Regardless, I can definitely relate to the sense of panic that sets in when contemplating clothing for something that isn’t familiar.  I may not have kids but if I were to set up on a fun girls trip I’d be a bit out of my comfort zone too.

I have put some thoughts and shopping suggestions together.

What to Wear on a Girls Trip

Where are you going?

For the intent of this blog post and the reader who inquired, I’m going to focus on choosing fun clothes for a trip to Nashville, a place I affectionately like to call a city that looks like a spittoon that has been rolled in glitter.  I love Nashville even though I don’t particularly love country music.  I appreciate that this city strongly leans into what it represents.  Even their TSA announcements are done by country western stars.  How can you not love it?   Nashville has that same fun, carefree vibe that places like Las Vegas and New Orleans have, an adult playground, if you will.  They invite a bit of a free-for-all way of dress, Vegas likely being the craziest.  Last week I was there and coined the slogan, What you wear in Vegas should stay in Vegas.  Good lord.  Where do some of these people crawl back to after their vacation is over?

Generally speaking, the first thing when planning a girls trip is to know what your itinerary is.  Obviously, what you would pack on a trip to the beach would differ greatly than what you would wear on a trip to the mountains or a yoga retreat.

Fun clothes over 40 for girls trips

Below you will find some shopping selections for this reader’s upcoming Nashville trip.  When making these selections I selected items for things like visiting bars, dinners out and general adult fun.

What I paid particular mind to was not selecting things too formal.  This reader and her friends aren’t attending a wedding or a gala.  They are out for fun.  Also, paying mind that she and her friends have kids of their own, I didn’t want to select things that were too young or trashy looking while also being perfect for a night out.  There are plenty of options out there that aren’t cheap, and I mean that literally and figuratively, and age appropriate.


Planning for some dinners out or an evening of fun, packing one or two dresses (depending on how long the trip is and what is planned) can be the perfect choice.  You don’t necessarily need a lot of accessories to look finished and can make a fun, playful statement with these dresses.  I also selected some jumpsuits in lieu of dresses that might be more comfortable for long nights.


Next, tops.  Fun tops are a must-pack for a girls trip.  They can be paired with pants you already own, can be dressed up with a nice pair of pants or a skirt and can be dressed down with jeans.


Accessories take up small space in luggage.  They can also be used to jazz up the more basic pieces of an existing wardrobe.  This reader told me she has her work wardrobe set.  I am sure that if she just dressed up some more of her basic items with some fun accessories, like the ones below, she be able to use what she already owns.  Additionally, these accessories can be used to finish the looks of the more fun pieces that will get packed.

I hope these selections help this reader and any of you planning a fun girls trip some ideas of what to pack.