top of page

A Ridiculously Simple Outfit Planning Strategy for Your Vacation

A collage of seven Western-inspired looks

My husband and I recently had a planned week away with some of his family, and I found myself needing to pack for a trip where the daytime temperatures would be warm enough to hit the beach, but the nights would be cool enough for a sweater or light jacket. In my 52 years on the planet, I've travelled extensively, worked in jobs where I had limited space for clothes and personal effects, and have just generally spent a lot of time with a suitcase in my hand, so I feel like I have an exceptionally strong packing game. I am reminded of this every time I'm at the airport; I am quite often standing at the check-in surrounded by people who are going away for a week or maybe a ten day vacation, and they have these giant suitcases (often bigger than the one I use to transport my shop inventory), and they're at the check-in desk holding up the line while they desperately try to re-pack everything because their bags are coming in overweight. Trust me, nobody wants to be that person at 5am in an airport, and with what airlines are charging these days, it's an expensive way to kick-off your trip.

Over the years I've developed a simple personal vacation outfit-planning strategy that really works for me, and it has resulted in me having more than enough looks for the trip, everything gets worn, and you don't end up hauling a bunch of stuff you're not going to wear all around the planet. Anyone can do this. All it takes is just a little bit of careful "front end" consideration before you start packing. The best part? Each time you do this, you'll get a little better at it. Nowadays, I can pack for a few weeks away in a pinch.


Outfit Planning for Vacation: The Basics

There really is no art to this other than to take the time to put a bit of thought into it before the suitcase comes out. If you take only one thing away from reading this article, let it be that. Once the suitcase comes out, commit to finishing your packing in one go. Leaving a half-packed suitcase out and open is a guaranteed recipe for overpacking. Every time you walk past that open suitcase you will throw something else in there. You know you will. Resist the urge. Trust the process. Take a moment before you start to create your plan and stick to it.

If you're historically not a planner, I suggest starting with sitting for a moment with a pen and paper and making a few notes. I still often do this for longer trips or trips where I have specific events to attend. I'll often even begin this process while I'm out and about in some waiting room or on a work break. Though I may be writing down what seems like the obvious, I feel like I'm getting a jump start on packing, and the simple act of writing helps me focus and gets my creative juices flowing. I can pretty easily visualize the items in my closet, and before long, outfit ideas start popping into my head.


Basic outfit-planning considerations, phase 1: the obvious stuff

  • How many days/nights are you away (i.e. how many bras and pairs of underwear will I need?) Don't forget to count any hotel stay nights in transit, and consider if you'll be willing or able to wash things either in a sink or via a hotel laundry.

  • What will the weather be like? Tropical and hot? Cold? Will I need layers? Heavy sweaters? Boots? Will I be walking a lot? Working out? Do the research here. Google the weather if you're unfamiliar. This will save you a lot of hassle if you have what you need going in.

  • Consider any pieces that you really want (or need) to have with you. Consider making one (or more) of these pieces your anchor piece(s) that you will rely on during your stay to help create multiple looks. Anchor pieces create cohesion in your vacation wardrobe and cut down on the amount of stuff you need to carry.

A Photo of a pair of black Dan Post Cowboy Boots

For our recent trip, I knew we would be spending our days casually relaxing by the pool or on the beach. Packing for that is easy (you barely need anything!), so I concentrated my efforts on packing my nighttime, casual dinner looks. I chose these distressed Dan Post "Jilted" boots as my anchor piece; a bigger piece than I normally would bring with me for only a week away, but I didn't have many restrictions, so to me bringing something a bit bigger felt a bit luxurious and apart from my norm.


Outfit planning phase 2: trying things on & picking your looks

Now that the anchor pieces have been selected, we're on to the creative part - trying things on. The act of trying things on ensures that all the pieces you end up choosing look right together; pant lengths work with shoes, high rise or low rise have shirt lengths that work with get the idea. In dong this, you will invariably start to see other outfit ideas emerge from within your selections, which will lead to the creation of more than one look for your trip. This practice really helps create a cohesive capsule wardrobe, and has the added benefit of helping you actually wear the clothes that live in your closet. Likewise I have also culled things from my closet on more than one occasion while packing for a trip, realizing that I hadn't worn something in ages and likely was not going to.

If you're a person with an overflowing closet in need of some organization and this practice makes you feel anxious and overwhelmed, don't worry about it. Dive in. You can finish organizing your closet in small stages over time, and you'll probably find that you're more motivated to do so once you've gotten into the rhythm.


Phase 3: add accessories & double-check foundation garments

A close up of a travel bag filled with turquoise jewelry

Phase 3 is a quick once-over of the looks you've chosen. Considering your looks, choose belts, hats, and jewelry. Here you'll likely find that you will be able to use the same accessories for multiple looks, so you don't have to go nuts and try to bring every little thing.

For our trip, I chose a selection of my turquoise and beaded pieces to take with me, all of which pretty much worked with any of the looks I chose.

Phase 3 is also a good time to make sure that you have chosen bras with straps that will work under your shirts, the right colors of undergarments (at least one nude set always seems like a good idea), and the right socks for workout shoes and/or boots. This is also a great time to take stock of the other things you'll need for your trip, like swimsuits, gym gear, and pajamas. Keep in mind when packing your basics - you can always wash things in a pinch, especially workout gear and swimsuits, so don't go nuts.

For our trip, the end result for me was a very cohesive, Western/Southwestern-inspired capsule wardrobe made up of pieces that were very interchangeable, appropriate for the cooler nighttime temperatures (layering!), and most importantly, looked and felt pretty much as I wanted them to. In retrospect I might have gone harder with the accessories (an area where I am inherently lazy and vow to do better), maybe layered them up a bit more, but on that first night I had literally seven minutes to get ready. Yes, seven minutes. So I guess that's another reason why having a wardrobe plan really makes a difference...sometimes your husband forgets to tell you the dinner reservation time has changed (because, men) and you have to get dressed fireman-style.


The Results: Seven Outfits in Seven Days

A split screen collage of a Western-Inspired outfit: a black vest, white shirt and tall boots

thrifted vest, similar | thrifted Gap jeggings | H&M Blouse (old), similar | vintage printed vest, similar | vintage concho belt, similar

A split screen collage of a Western-Inspired outfit: a black vest, white shirt and tall boots: A khaki shirt dress, black boots and concho belt, a long aztec cardigan

vintage LOFT sleeveless shirt dress, similar (on sale!) | vintage concho belt (as worn on Day 1) | thrifted Aztec open cardigan, similar

A split screen collage of a Western-Inspired outfit: a lace keyhole neckline tunic top, skinny jeans and tall black boots

thrifted free people tell tale tunic | thrifted Gap jeggings (as worn on Day 1)

A split screen collage of a Western-Inspired outfit:a lace tee, denim skirt, a serape stripe tunic shirt, and tall black boots

thrifted Zara sheer lace top, similar | thrifted Old Navy raw hem denim skirt, similar | turquoise buckle vegan leather belt (old), similar | Tasha Polizzi flannel serape tunic (old), similar | turquoise heishi bead necklace (old), similar

A split screen collage of a Western-Inspired outfit:a pair of bootcut jeans, a sleeveless lace blouse, a long aztec print cardigan, and a pair of black strappy heels

thrifted Lipsy sleeveless blouse, similar | turquoise buckle vegan leather belt (as on day 4) | Grace in LA bootleg jeans (old), similar | thrifted cardigan (as worn on day 2) | H&M sandals (old), similar | beaded earrings (old), similar

A split screen collage of a Western-Inspired outfit: a blue flare sleeve blouse, a denim skirt, a concho belt, and a pair of tall black boots

Ryan Michaels flare sleeve blouse (old), on ebay (sm), on ebay (lg) | black concho belt as worn on days 1 & 2 | skirt as worn on day 4

A split screen collage of a Western-Inspired outfit: a white shirt, aztec print body con t shirt dress, and tall black boots

thrifted No Boundaries Aztec print dress, similar, similar vibe | white shirt as worn on day 1 | heshi turquoise necklace as worn on day 4


bottom of page