How To Pack For a Vacation: A Fashion Stylist's Guide

Raise your hand if you hate packing.

I'll tell you a dirty little secret.

As a stylist, I also hate packing.

For me, it is particularly because I like to have all my choices and options. I feel like I can tell a client exactly what to bring on a trip because I'm not emotionally involved, but with my own clothes, I'm very emotionally involved. I equate it to sort of when I was young and single, I could give someone else boyfriend advice, but I couldn't necessarily take that same boyfriend advice myself. So this is that same sort of catch all. But anyway, so I'm going to take you through my process for I'm going on a warm weather vacation, but to a few different locations. So I need to pack more than just like a weekend trip. And we have a different. A few different things on the docket. But.

But I'll take you sort of through.

The process as an example and hopefully that will help you if you're going somewhere. I start by going to grab my out of season stuff. So in this case my summer stuff. And I keep that in a separate place. I keep a lot of my summer stuff or my out of season stuff, I should say, in a different closet. So I come in here to grab the things that I'm missing. I've already gone through my dresses, so that's on a rolling rack in my closet. And now I need to find some shoes. Next, I go through all the categories of things that are going to be going on. We're going out to dinner, we're going to be at the beach, I'm going to want to exercise, we have a party to go to, that kind of stuff. And then I pull everything I think, think I might want that. I've worn this past season that I really enjoyed. So I don't think that vacations and traveling are times to try out like new things. I think those are the times for your never fails. The stuff that you know works really well for you and even as outfits have worked great. However, if you're like me or many other women, your weight might fluctuate. So. So you got to get it out and then you got to try it on.

So this is all the stuff I.

Pulled thinking I might like it. I certainly don't need like five or six pairs of pants and all those dresses and all those T shirts and all those jackets. But I like to make sure I have layers. I have a. I like to make sure I also have a color sort of palette. So a lot of denim, some tan, some whites. A few pops of color here and there. Those are sweatshirts that I need to think about and those are cover ups. But that's a lot of the daytime and going out stuff which for sure needs to be pared down. And then I pulled out all these shoes for sure. I'm gonna bring two pairs of sneakers because my feet like to switch off. Not sure if I need those. Those are two going out sandals. Again, not sure I need both. Some beach sandals, some daytime sandals. Those are probably redundant also, but those are the ones I wore the most this last year. And some hats and some accessories and that's like bathing suits stuff and exercise stuff. Next step is for me to try things on the way is outfits. But I remember wearing them over the summer and in the fall and then go through and make sure that each, each outfit, there's like a hair in my eye. Sorry. Each outfit has layer ability. So if it's warmer than I expected, I have something that's less heavy. And also if it's colder than I expected, I have the ability to either put on a closed toe shoe with it or add a scarf or a jacket or something like that. So that way if it's cooler in the evening, if it's warmer during the day, I always look at the forecast. But as we all know, that changes a lot. And then I like to make sure that everything can be worn with multiple things. So each individual piece I'm bringing can be worn at least twice in a different way. I'm going to try and take you through it, but yeah, I'm going to try and take you through it a little bit.

So I'm going to start with some.

Bottoms to figure out which ones to actually bring. I probably don't want to bring more than three. And I want to make sure that I have the right shoes to go with them. Where I can either wear it out at night or I can also wear it during the day if we're gonna go shopping or to lunch or something where you're not for us. Where I'm not wearing like my exercise clothes or I'm not wearing beach clothes. So definitely don't need like multiple pairs of white jeans. One is a wider leg, one is more of a straight, a slim straight. I have two pairs of like khakis, one is lighter, one is this flatter.

Paint, a couple pairs of jeans.

And then I'm pretty sure I'm gonna bring these black. They're like a black chino that I'm pretty sure I'm bringing. So why don't we start with that? Okay, so one other thing I want to mention is taking pictures. I know I talk about this all the time, but I think taking pictures, just those regular mirror selfies are super helpful, especially at a time like this, because you can go back and look in July or August and look at what you wore and see how you liked it. And that can help you recreate those outfits for when you're going away for the off season. Because I think, at least for me, when I'm somewhere that it's snowy, it's so hard to imagine somewhere sunny. And then I go somewhere sunny and I'm like, how can it be snowing somewhere? I mean, it's 80 degrees and I'm so hot. So that helps me sort of capture it back. All right, I'll show you what I did with these black pants.

In my humble opinion, vacation is not the time to wear the most outstanding, earth shattering sort of outfit. It's the time to wear your basics where you can have versatility and still feel totally put together and change it up a little. So again, these pants, I love them. They're nearly low tan, they're lightweight. They are my go to for feeling great because I can dress them up, dress them down. I would do it, I don't know if you can see. I would do it with this kind of shoe for an everyday with just the white T shirt. And if I was going out, I.

Would put on the heel.

So to me that's saying that those two shoes get a check because they're working with an outfit. And then I'm going to see what else I can work these shoes in with. I would change out my jewelry. Like this would be a great daytime one. I could put on something a little heavy, heavier if it was for the evening. And then I have to think about a topper. Okay. If it's daytime, this is one of my never fails. It's lightweight, it's a great jean jacket. It's cropped, so it works with this higher waisted pant. But I also know that it works with my dresses. So again, getting a check in the box because I know it has multiple uses. And this is good for the casual shoe for sure. And if I was going somewhere casual at night but wanted to elevate it a little, I don't feel like these sandals, that this is an outfit is so out of whack. So now I have two sort of options for these pants, for the jacket. We're building, we're building. So now I tried to Take these pants into nighttime. I definitely like them with this shoe.

I.

Okay, medium like them with this shoe. Instead of knotting it, I added a belt, which, honestly, I've had this since before I met Greg. But remember how in the 90s, our pants were up here, and then they went down here? And so I haven't been able to wear it in a long time. Now the pants are up there. I can wear it again.

So.

And this is a lightweight black leather blazer, which I love. It goes with a lot of things, but for some reason, with the black and black, it feels a little like it might be fine for a city. It doesn't feel total beachy. And again, we're gonna have some beach time, but also some warmer city time. So adding a pop of color in a scarf just sort of helps it not feel so wintry. So I could do that. But if it's not super cold out, you know what else I can do that would make it even a little feel a little more elevated? I could lose the blazer if it's not super cold. This would be perfect. And just add this guy, which, again, now, all of a sudden, I feel a little more, you know, chic and glamorousy, you know, relatively speaking. And then it's going to help me decide what bag to bring. So I'm going to show you how this works. This is one of the bags I was debating on, and because it has the blue and it goes with this, it sort of takes this black and white outfit. And now all of a sudden, I feel a little more special if we're going out in the evening, but yet it's still a T shirt and a pair of slacks. So I think all of these pieces are going to come. This guy's still a maybe, but so far, all of these have multiple uses, so I'm now gonna welcome you into the craziness, which is my brain. So this jacket is super lightweight, sort of silky. I picked it up at Zara for Black Friday. I wasn't sure I was gonna bring it. I sort of thought I was taking it or getting it to have for next season, but I really like the shape and how it gives more of a tropical vibe. And I even like how it works with the bag. But. Okay, now you're gonna get my craziness. Now there's a little bit of me that likes this shoe better than this one. So now he gets to be. He might get a reprieve. And this might bump out the black blazer for coming with, because I also Think this would look really cute with a pair of white jeans and a tank top or a silk camisole. I also think even with a pair of blue jeans and sandals it could be sort of cute. So we're building okay, this also with the same pants sort of changes it up and it'll look really cute. I know with white jeans cuz I wore it over the summer that way. And I think it's going to look cute with blue jeans and just sort of a flat sandal also. So I feel like now probably like three nighttime outfits, two or three nighttime outfits and like two or three daytime outfits with these pants. So they're for sure going well. I thought of one more. So again it's easy to bring another belt or another necklace. It's the shoes and the pants and the jackets that take up so much room. So this, I love the neckline on this tank top. I am not wearing the proper bra so I need to jot down on a piece of paper and actually I'm including for you guys a downloadable checklist for packing so you can do it on there. And I'll write down, you know, racerback bra in black so that I remember I need it for this outfit. But totally this feels a little more. It feels like sophisticated but beachy. And then because of the red belt, I did not want to do my turquoise wrap and this neutral tan one goes almost on every vacation with me because I bring it on the plane so we can do the same sort of wrap still show the necklace and yeah, remember I said try everything on. These are my J. Crew white boyfriend jeans. I don't think I've worn them since they were washed.

Wow.

And in many months and probably have a couple pounds on me. So let's see if as I'm trying them on they warm up and stretch a bit. And if they do, I think they're going to be the best option because I can wear these with sneakers also. But I might need to loosen up in order for that to happen. Tbd. You're definitely starting to loosen up, so that's a good thing. This I think also could be a nighttime or a daytime walking around look. This is that shorter jean jacket and I'm not sure it's going to work with this because these pants are more of a mid rise than a high rise and also because this is super frayed. These are frayed at the bottom. So I feel like the jacket with it is okay. I may bring. I have another jean jacket that's a little longer and even Though that is redundant. Sometimes I feel like if I have the space, I'll stick the other one in. If I don't, this would be fine. And the other thing I can do is, yes, Need a different bra. Just throw on again, A scarf is easier to pack. And this, because it's so sheer, just takes the place of like a little cardigan and looks really nice. So bringing extra scarves, extra necklaces, and extra belts takes up much less room and pretty much transforms the looks. The other thing I wanted to say is that I think black and white and adding that luggagey tan sort of color really helps elevate an outfit. It's a color combination that just looks. It just looks rich. And so if you're ever in doubt, those are three that work really well together to just kind of look classy. There's some more of that whittling down. So same jeans, same shoes. A nice little lightweight top that also looks good with plain denim. And again, just a little. It has some sparkle. Same necklaces, just this time I doubled them. But it's okay with this bag. It's not great. And then I was thinking I was going to bring this to add a pop of color. But I've used the other bag for most things, and where I haven't used it, I haven't chosen to use this. So I have a feeling I will end up bringing this, which is another tried and true. And it just kind of goes with everything. It can be crossbody. You can play around with the straps. So I have a feeling this guy's going to stay home. And this will end up coming with me. It would look nice with all black. It'll look nice with all white. It'll look great with some of the brighter colors. And, yeah, whittling it down. And I can wear the tan wrap over this, too, or a jean jacket. These are the same white jeans, and I'm so grateful that they are stretching out as I'm wearing them. Just a plain sleeveless, blue and white tank. While it definitely looks good with the little red mule or loafer, the reality is I feel like I have enough nicer outfits that if I'm gonna wear this, I would probably put it on with Birkenstock or even one of the other sandals I was thinking about bringing. And I don't think I really need to bring these.

So that's cute.

And I could throw this on with the jean jacket and that would look cute also. So these don't need to stay.

Bye.

Bye. They stay home. Two different size heels On. But this is a nice flat. This is that tan heel that I wasn't sure if I was going to.

Bring, but I think I am now.

And again, same tank top, same jeans.

Bag I decided I was going to bring.

And this is just a navy cashmere cardigan. But again, sometimes lightweight cashmere. Cashmere feels so good at night when you're in a warm destination because either.

There'S air conditioning or it gets significantly.

Cooler in the evening. So this is a nice one that can kind of throw in.

And in fact, if I wanted, I.

Could wear it just as a shirt on its own, not wear something underneath and have, you know, it be a little deeper cut and pile on some of those pearls and feel all of a sudden much dressier than wearing a T shirt. So another option to layer on more confusion. The same outfit looks good with sneakers. If you're gonna do something more sporty during the day, or if it was cooler and I needed to have this sweater on and off, really, the shoes change it all up. Look how much taller I am on this one. But the shoes change it all up. And so, again, multi purpose. I think these pieces have earned their right in the suitcase. I wore this dress over the summer and need a little help zipping it, but I'm pretty confident it's going to zip. I like it with the flat sandal, and I sort of like it with the heel, too. I don't think it changes the outfit that much, but depending on where we're going and what we're doing, that's the beauty of a dress, is that it's awesome because it's one and done and you throw it on. But sometimes there's not the ability to change it up as much. It doesn't offer as much versatility. So, like, I could wear during the day with the flats, I could wear at the night with flats. I like it with this bag, and I like that it adds a little color. So he gets to come. This is another one of those. One and done. Oldie but goodies. It's super lightweight. I like the color. There's pockets. You know how good it makes it when a dress has pockets. And it goes back to all the other bigger items I was bringing. It works well with these shoes. It works well with the bag. I can wear this necklace with it, and it fills up the space nicely. And I can throw on the shorter jean jacket with it if I want. I can throw on one of the cashmere wraps. That works. I could also belt it if I wanted with that little Hermes belt. And that could help take out some of the volume. But personally I really like the volume. So he's another guy that's coming. So I'm losing steam. Packing is like totally draining. Anyway, I have two black dresses that I was gonna bring for evening that was. I mean, that was on the rack. I actually had four. I narrowed it down to these two. And I think while I love both, I'm gonna bring him because I just know it works. And it sort of could be a little dressier if we end up doing something for a New Year's or something like that. I feel like this is a smidge dressier than this. So I have three nighttime dresses.

I have.

Dark jeans or black pants and white pants that I can wear at night time as well as like a blue jean if it is a more casual kind of thing. Blazer. I need a couple of daytime dresses, a couple of COVID ups and I think I'm gonna be good to go. I think I even can narrow down the shoes. It's dressed before two and it's what my grandma probably would have called the schmata, which is a rag, but it is so soft and so airy and I love the bright colors. I love that I could wear it over a bathing suit with my flip flop. Or I could also wear it in the evening with that nude bag and the sparkly sandal. And it sort of works for both. So again, because I feel like I'm in Shark Tank for those reasons he stays in. This is another one of those dresses that could sort of go daytime to evening. It's just an easy halter dress. Again, have to remember to bring the right pasty kinds of things to go under it. But depending on the jewelry or the shoe I wear with it, it's really easy. Colorful. I like. This is the reason I have to bring that shorter jean jacket because this one works better with a Dr. Dress. And thank goodness I swapped this guy out because he's going with everything. So yeah, I was on the fence about this, but I am definitely bringing it. It's fun and a little different. The one I was on the fence about but had it for years. I have not worn it that much because it feels a little fancy sometimes as a beach cover up and I haven't traveled. Thank you, Covid. So maybe that's why I haven't worn it. So I think I might bring it to go out to dinner if I was going to wear a shawl with it or a scarf with it. I think it also is hard to sort of put something over and make it look intentional. So what I would do is I would take this scarf that has the fringes sort of like the bottom of it and wrap it around my neck a couple of times, because keeping my neck warm often keeps me warm. And then I think it sort of mimics and keeps me warm without losing the integrity of the caftan kind of thing. And I could wear it with a flap, but I do think I like it with the higher heel, especially because the tassels are so long. So, yeah, this one's, like, in that maybe category, if there's room. Okay, so let me show you what this all means.

The end of the try on this is all the stuff that's coming because it went with a bunch of things. These are my things that are my questionable maybes, if there's extra room. And these were all the no go's not necessary. Shoes are a hot mess. But I know I'm not bringing the red ones, and I'm not gonna bring those studded guys. Those are my favorite beach shoes.

Those I also wear for the beach, and I do think I'm gonna bring.

Both going out at night shoes. I'll definitely wear one of the sneakers on the plane, and I will likely wear this jean jacket on the plane, One of the scarves, and probably one of the sweats over there.

So.

Yeah. Was this helpful? It was helpful for me. You guys helped me keep me accountable, and I got rid of a lot of stuff, and I did it. I have to remember to add in those couple of bras, a couple of pairs of underwear that were in the wash and or something else that I wrote down. Oh, my beach bag. That was the other thing that I didn't take out, So I got to take that out.

But other than that, feeling pretty damn good.

Yeah.