Planning for My Annual Girl’s Trip!!!

Well, it’s time for my annual girl’s trip with some of my besties, and I couldn’t be more excited.  We started this tradition in 2017, so this is our 3rd trip together as a group.

In 2017 we went to Mexico!  You can click HERE for just a handful of pictures.

In 2018 we went to New York!  You can click HERE for a full trip recap outlining what we did and what I wore.

This year we are headed to Boston, and I’m so excited to explore a new city with some of my favorite people!  Truth be told, I’d be okay with just getting a hotel room in Dallas and having uninterrupted time with my girls, but it is definitely fun to pack up and go somewhere.

We’re only going to be gone 4 days, so I don’t need to have that many outfits, but here’s the deal….I’m a chronic over packer. It’s stupid, really.  I’m TERRIBLE at deciding outfits beforehand and really like having options, you know for weather, OR JUST MY MOOD.  Haha! Today you are going to get a tiny peek into what it looks like for me to get ready to head out of town.

PACKING PREP

Besides the clothes (which we’ll get to in a minute), here’s what I reach for when heading out of town:

MY SUITCASE:  Click HERE. (This brand goes on sale every so often, and I’d recommend waiting for a sale because the pieces are expensive.  Expensive, but worth it.  Because I’m telling you, this luggage is AWESOME.)

MY PACKING CUBES:  Click HERE.  These little bags are UNBELIEVABLE.  (If you want to see how well they work, click HERE and scroll to the bottom of the post.)

MY NEW SKINCARE AND MAKEUP TRAVEL BAGS:  Click HERE.  They come in a pack of 2. I use 1 for makeup and 1 for skincare.

MY TRAVEL SKINCARE:  Click HERE.

WEATHER FORECAST

We’re lucky, because it looks like the weather is going to be pretty fantastic!  We’re talking an average of Low 40s to High 50s, but bright and sunshiny most of the time. I’m thinking that during the day when we’re walking around it will be mid 50s.  A week ago there was rain in the forecast, but it looks like that has now been pushed back!  Yay!

THE ONLY 3 SHOES I’M TAKING

Since the weather is going to be pretty mild when we are walking around during the day, I’m leaving my UGGs at home.  I’m taking my black Adidas sneakers (found them ON SALE at Zappos!), my new black wedge booties from Tuesday’s post (I originally found them at Lord+Taylor, but they are at Nordstrom too!) and a pair of cage heels that are several years old.

MY PROCESS

I’ll be doing a trip recap next Friday, but today you are getting a peek into my outfit planning process.  And my “process” is basically me putting on a lot of clothes and taking a whole bunch of selfies.  Haha!

That’s actually a great tip. When planning your outfits for an upcoming trip (or event), take a picture of yourself in the outfit contenders.

I find that often times when I take a picture in something it’s not as cute as I thought it was.  OR I might not have been totally feeling the outfit, but then I see it’s super cute in pictures.  Doing this really helps me narrow down and decide what pieces to take, otherwise I’d just throw caution to the wind, pay the extra baggage fee, and pack my whole dang closet.

LEGGINGS OUTFIT POSSIBILITIES

Let’s start with leggings outfits.  Y’all know that I’m all about comfort, and since I’ve recently found some sweaters that are leggings appropriate, I definitely wanted some outfit choices with leggings.

And depending on the weather, I can wear either my moto jacket or mid length puffer with each of these outfits.

This sweater is a new favorite, it also comes in white and black, and it’s perfect for leggings.  I’ve already shown you this sweater with black jeans, with office pants, and with blue jeans.  I love it.  It’s super soft and super versatile.

Let’s talk about this cute little bag.  I don’t travel a lot, but I’ve learned that I personally don’t want a big heavy bag weighing me down when I’m walking all over and exploring a city.  I carry just the essentials:  my license, a credit card, a small amount of cash, my phone, and a lipstick and a lip gloss.  I also like that wearing a bag cross body keeps my hands free and my things close to me and safe.

exaggerated neck relaxed fit sweater / favorite earrings / leopard cross body bag / moto jacket / high waisted leggings/ black sneakers with gold accents

Right now, I’m thinking that this is the outfit I’m going to wear on the plane and for our first day.

The outfit on the left is cute on it’s own..but it gets kicked up several notches with the brightly colored plaid scarf and  the moto jacket !  This moto jacket has a removable hood (I’ve taken it off for most of these pictures), and I love the brass hardware and zippers.  This jacket goes with all of my casual outfit possibilities, but I can also wear it on our one fancy night.  I’m wearing a medium in the jacket

I like that this particular scarf is small, because if it does get warm, I can strip the scarf off and tie it around my bag.

exaggerated neck relaxed fit sweater / favorite earrings / leopard cross body bag / plaid scarf / moto jacket / high waisted leggings/ black sneakers with gold accents

And depending on the weather, I can either grab my moto jacket or mid length puffer!

The same outfit formula, but instead of a solid color sweater and a plaid scarf, I’ve got a striped sweater!  I’m wearing a small, so the sweater is definitely oversized.  This sweater also comes in tons of solid colors, and you’ll see one of those with jeans in a minute!  It’s a really great sweater.  It’s not clingy at all, and it can be worn out or 1/2 tucked.

sweater / favorite earrings / leopard cross body bag / moto jacket / high waisted leggings/ black sneakers with gold accents

And of course if it’s colder, I’ll grab the puffer!

This puffer is warm, it’s water resistant, the pockets are deep, and it covers my bum!  The quality is awesome, and the price is INCREDIBLE!!!  This jacket also comes in grey and navy.

I got a medium, but if I didn’t need room in the chest, I probably could have stuck with a small.

For this next outfit, I went all black. And then I paired the all black outfit with the prettiest blush scarf.  This scarf is quite a bit bigger than the above plaid scarf.  In fact, it’s big enough that you can really wrap up in it!  Which brings me to another tip.

Scarves are great on travel days. This one is big enough that it’s great for warmth and can be wrapped around your shoulders or used as a small blanket, but it also can double as a pillow.  I mean, I love to grab a quick nap on a plane.

If I wear this outfit, I’ll wear it with sneakers instead of my Uggs.

high low sweater / blush scarf / favorite earrings / leopard cross body bag / moto jacket / high waisted leggings/ black sneakers with gold accents

Yet another leggings, sweater, and scarf option.  The perfect outfit formula for a travel day.

The sweater is quite oversized, verrrrrrrrrrrrrrrrry soft, and I love the mock neck.  It has a thick band on the bottom, and it can be worn out with leggings or jeans.  I’m wearing a small, and it’s still a very relaxed fit.

You can click HERE to see this same sweater styled with both the best black pants ever and jeans.

ivory sweater / blush scarf / favorite earrings / leopard cross body bag /puffer jacket / high waisted leggings/ black sneakers with gold accents

So this next outfit isn’t leggings, but it IS a glorified sweatsuit.

YES, PLEASE.

For size reference, I’m wearing a medium in the top and a small in the joggers.  It’s from the Lou and Grey SignatureSoft line, so you know it’s stupid soft.  I would say that it’s as comfy as pajamas, but it’s actually more comfy than some of my actual pajamas are.

sweatshirt (30% OFF right now!) / joggers / my favorite earrings / black sneakers with gold accents

And then I decided to take things NEXT LEVEL COZY…I topped it off with a blardigan.

WHOAH.

baby blardigan / sweatshirt / joggers / my favorite earrings / black sneakers with gold accents

*********************************************************************

JEAN OUTFIT POSSIBILITIES

I’m a little worried about being cold in just leggings, so I have some outfit possibilities with jeans as well.

You’ve seen this sweater before, but I thought it could be a fun option for a girl’s trip!  It’s super versatile, and looks great dressed up a bit too.  You can click HERE to see it styled with black suit pants.  I sized up to a medium in this sweater.  I’m wearing a 4Petite in the jeans, and I probably could have sized down to a 2P.

pink and red polka dot sweater  / favorite earrings / leopard cross body bag / moto jacket / leopard cross body bag / cropped girlfriend jeans / black wedge booties / bracelets (use the code FALLFUN for 40% OFF)

I grabbed this sweater back during the anniversary sale, and I love it.  Sadly, this striped version is sold out, but it is available in lots of solid colors.  It’s really soft and warm, but it’s not bulky!  I’m wearing a small.

cashmere turtleneck sweater / favorite earrings / leopard cross body bag / similar new balance sneakers

cashmere turtleneck sweater / favorite earrings / leopard cross body bag / moto jacket / similar new balance sneakers

Okay, so I definitely love this outfit and would say this is a top contender for Day 2 or 3.   It’s bright, happy, and I think it will look cute in pictures.

I adore the color of the sweater, and I especially like how this scarf looks with the sweater.  However, I was thinking that I was going to wear the scarf with the first leggings outfit on day 1, but since this outfit has the same scarf, I might want to change to a different scarf on the other outfit.  I don’t want it to look like I’m wearing the same outfit on different days.

I am IN LOVE with the color/pattern combination and how the outfit came together.

sweater / hoop earrings / plaid scarf / moto jacket / leopard cross body bag / cropped girlfriend jeans / black wedge booties

This is the same outfit from a different view, but the lighting is terrible here, and the sweater color isn’t very well represented.  Refer to the color on the Nordstrom site.  You’ll see online that it’s gorgeous and vibrant, but I don’t think its”red” as it claims.  It definitely leans to a bright coral.

And I think I’ll change out these cropped jeans for my AG jeans from several years ago.  I’m not sure I’m going to want as much ankle showing as these jeans would allow.

sweater / hoop earrings / plaid scarf / moto jacket / leopard cross body bag / cropped girlfriend jeans / black wedge booties

This next outfit is monochromatic, and I dig it.  This sweater wouldn’t fit under the moto jacket, but it would be a great option for me under the puffer.  I like the idea of being able to take off the puffer if I’m too hot and have a sweater where I can push up the sleeves and cool down easily.  Seriously.  I hate being hot.

The reviews on this sweater are phenomenal.  I’m wearing the x-small/small.

poncho sweater / hoop earrings / leopard cross body bag / cropped girlfriend jeans / black wedge booties

Following the same outfit formula here again with a sweater, a scarf, and the moto jacket.

I thought it would be pretty to go pink on pink.  The sweater is called “pink compact”, and I’m wearing a small.

crew neck cashmere sweater / blush scarf / hoop earrings / moto jacket / leopard cross body bag / cropped girlfriend jeans / black wedge booties

Black on black again here.

This particular black sweater is oversized and is definitely long enough to wear with leggings.  I’m wearing a small.  It’s very soft and a perfectly oversized and relaxed fit.

black sweater / hoop earrings / moto jacket / leopard cross body bag / cropped girlfriend jeans / black wedge booties

Leopard and pink together is always a good idea.

And y’all!  This is my Walmart sweater you saw back on my Snakeskin on a Budget post! It’s soooooooooooo good.  UNDER $30, wonderfully soft, perfectly slouchy, and this vibrant hot pink color!

I’m wearing a small, and it’s still over sized, so I would suggest sizing down if you don’t want it tunic length and if you aren’t going to be wearing it with leggings.

AND GREAT NEWS!  These Kendra Scott chunky hoop earrings (that are light as a feather) are ON SALE!

hot pink slouchy turtleneck sweater  / leopard cross body bag / hoop earrings / moto jacket / leopard cross body bag / cropped girlfriend jeans / black wedge booties

You saw this sweater above with leggings and the blush scarf.

Here I switched the pants and the scarf.

ivory sweater /plaid scarf / favorite earrings / similar AG jeans/ black sneakers with gold accents

Depending on the weather, I could wear this outfit with the moto jacket (on the left) or with the white puffer (on the right).

CONFESSION:  When I ran into Target to get a couple of travel sized items just yesterday, I left with this white puffer.

#OOPS

I’m wearing a small in the puffer, and I still have quite a bit of room, so definitely size down.

ivory sweater /plaid scarf / favorite earrings / similar AG jeans/ black sneakers with gold accents

moto jacket / white puffer

*********************************************************************

DRESSY OUTFIT POSSIBILITIES

One night we are going to a nice steakhouse, so we all decided to get dressed up a bit.  I’ve got a handful of choices for our “fancy” night.

SEQUIN TOP AND COATED DENIM

I’m thinking this is my top choice, but we shall see when then night arrives.  I think it’s so different and unique.

The top is oversized, which is my jam these days.  Because of this, I like it with the really skinny coated denim.

sequin top / hoop earrings / moto jacket / similar black coated denim / cage heels are several years old

sequin top / hoop earrings / moto jacket / similar black coated denim / cage heels are several years old

BLACK SEQUIN TOP, VELVET BLAZER, and JEANS

This is one you’ve seen before.  I took a sequin shirt and topped it off with a luxe velvet blazer.  I love having the option of throwing a layer on that isn’t a bulky coat!!!  And this blazer doesn’t just provide warmth, it provides all sorts of sassy style. It’s got a notch collar, button closure, and a bit of stretch for a very comfortable fit.  The quality is amazing.  It’s fully lined with a silky satin with a bit of a contour at the waist for a super flattering blazer fit.

I think a blazer, jeans, and heels is a great look whether you’re dressing up for a holiday party or just heading out for a night on the town with your man or some girlfriends!  I’m wearing a medium in the shirt and a petite medium in the blazer.

Let’s talk about the jeans for a second.  I first introduced you to them on last Friday’s post (maybe you’ll remember me wearing them with the pink and red polka dot sweater), and I’m a big ol’ fan.

They are from Wit and Wisdom, they have the Ab-solution technology, and like all Wit and Wisdom pieces they are stupid comfy.  These are their girlfriend jeans.  They are a bit lighter of a wash than the ankle jeans I’ve been showing recently, they aren’t quite as fitted, they have a bit of distressing up around the hips, and they are more cropped than my ankle jeans and a bit wider at the ankle and through the calf.  I’m wearing the 4 Petite, but I would actually suggest sizing down. I have plenty of room in these 4 Petites and think a 2 Petite would be a better fit.

velvet blazer / black sequin top / hoop earrings / bracelet / cropped hem girlfriend jeans / similar leopard pumps

You’ve seen this skirt before, but here I am styling it just a bit differently with a moto jacket, tights, and over the knee boots.

black cashmere sweater / hoop earrings / bracelet / leopard bow skirt / moto jacket  / my favorite opaque tights / similar black over the knee boots

WHEW!  That was a lot of outfit possibilities!

I’m hoping that my crazy trip prep has given you some outfit ideas for a possible fun upcoming trip of your own…or just a trip to the grocery store.

I’m sooooo excited about this trip!!!  As a busy mama, a little away time with girlfriends is just good for the soul.

That’s it for today, y’all.  I hope you had fun playing around with outfits with me. I’m planning on doing the trip recap next Friday, but I’ll see you back here on Monday for some Monday musings.  Have a wonderful weekend with your people!

Filed Under: Fashion 24 Comments