Reader Request: Family Vacation Style

dressing for family vacation

Reader Ursula posted this question to Facebook:

Have you written about how to dress for family vacations (Disney specifically) and not look like you are trying too hard (or too little as the case may be)? Struggling with function and body image on this one.

I’ll admit to never having entered a Disney theme park and I don’t have kids myself, but I’ve been to loads of amusement parks for day trips and taken plenty of vacations – with family and alone – that require similar amounts of walking and standing in line. (Think art museums in Florence in June. LINES, people, oh the lines.) So although I can’t speak from direct Epcot-based experiences, I will make my suggestions and ask those of you who have done Disney or similar family trips to lend a hand in the comments!

Feet first

Last year I was reminded that in hot weather, feet swell and swollen feet in even the comfiest of ballet flat-like shoes worn without socks will lead to blisters. This year I was reminded that walking around for 8+ hours in ANY temperature will cause your feet to swell and  flats can be killer in those cases, too. If your feet hurt, all bets are off, so consider your footwear choices first.

Audi’s solution is supremely comfy sandals which allow your feet to breathe and can have a little more leeway for swelling. Try comfort brands like Clarks, Dansko, and ECCO for starters, but sportier, casual brands like Crocs and Teva can work, too, depending on the clothes you plan to wear.

My feet can get just as torn up by sandals as they can by flats, so I’m thinking upgraded sneakers instead. If you don’t need loads of support, classic Keds or Chuck Taylors will look equally cute with sporty dresses and with shorts. But since most of us can’t do something that flat for hours on end, check out the current Keen offerings – especially the Maderas and Coronado – as well as the Teva Freewheel and Dr. Scholl’s Jennie.

Accessories next

No, really. Accessories are key to both comfort and style when you’re on vacation, especially if you’re both walking and hauling.

For starters, make sure you’ve got a bag that is lightweight and comfortable to carry. Something that can be worn crossbody like this LeSportsac bag would be great – water resistant and absolutely featherweight. If you’ve got to haul diapers, bottles, or other heavy kid supplies you will need something sturdier, of course, but if the whole gang is mobile and carrying their own stuff, pick a lightweight bag for yourself.

Track down a pair of sunglasses that you totally love. In all likelihood, they’ll be on your face more than off, so don’t settle for an OK pair. Target has a great selection, and if you’re willing to spend more I love the shapes at Madewell. This is a great way to up your style quotient, even if the rest of your outfit is super casual.

And consider picking a single set of simple jewelry for the whole trip. Stud earrings or smallish ones that won’t get caught in hair, a gold or silver chain necklace, and a bracelet or watch. Jewelry may seem like overkill, but opting for classic, understated items will help you look more polished without feeling over-embellished.

Clothing choices

In my opinion, there’s nothing wrong with shorts and tees for family vacations, so long as they’re actually comfy. Shorts can chafe and bunch on certain bodies and especially in hot weather, so bear that in mind – blister block or talcum on the thighs can help, as can wearing slip shorts (unless they make you overheat). Also remember that you are likely to wear a size larger in shorts than you generally do in pants, so consider sizing up. Also also super long shirts worn with shorts may throw off your proportions, so pick tees that balance you out. I’d do v-necked tees in solid colors, tan or denim shorts, and cute sneaks. Simple, clean, casual but classy.

If you want to have some non-shorts options, think about dresses from athletic brands like Athleta and Title Nine as well as brands that offer washable, durable knits like Land’s End. Dress, sunnies, sneaks, bag, done. And if you’ve got any slightly fancier stuff planned, add a scarf and some jewelry to your suitcase to dress up your knit frock.

Protect your skin

A sidenote to style, but I’m throwing it in anyway. SLATHER YOURSELF WITH SUNSCREEN. Make sure you have protection for your face and lips, too. Since you will likely be getting your photo taken approximately every 12 seconds, consider a tinted balm like my beloved Fresh Sugar. One swipe and you’ve got SPF 15 and a hint of color.

If you’re camping or hiking instead of hitting a theme park or roaming around a major city, some of these suggestions will need tweaking. Rugged footwear, appropriate bags, and wicking clothing may all come into play, so adjust your choices depending on your destination.

In terms of trying too hard? Unless you’re dripping logos and diamonds while riding the rides, I doubt anyone will notice. Maybe I’m being naive, but my guess is that most of the families roaming around the Magic Kingdom are too busy building memories and snacking and laughing and posing with princesses to care what other families are wearing. I hope so, anyway.

Image courtesy snoopdrew

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Originally posted 2014-06-18 06:44:04.

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30 Responses to “Reader Request: Family Vacation Style”

  1. motherhoodispainless

    Great suggestions, Sal! I’d only add one – find a cute hat – I know I feel loads better if the sun isn’t shining in my face. It can also help disguise hair that’s fallen flat after a day of sweating!

  2. KimM.

    I haven’t been to Disney either but have been to a few amusement parks in my day. I would suggest quick dry clothing if you like water rides of any sort. I remember getting on a ride advertising “you might get a little water spray on you.” No, I was drenched head to toe. Looked like a drowned rat after that ride. So after that experience I wear quick drying clothes and water shoes. A waterproof bag of some sort is essential as well.

  3. JB

    These are great tips! I personally don’t like to travel with expensive sunglasses because I ALWAYS end up losing them. Hats are another great accessory for stylish sun protection – although obviously not if you’re going to be going on any crazy roller coaster rides. Also, though I’m a big fan of packing light, I think if blisters are a possibility then being able to alternate between at least two different pairs of shoes will be helpful. (Bodyglide is great for preventing blisters, by the way.)

  4. Jocelyn

    I went to Disney in October, and my main suggestion reitierates Sally’s first one – comfy shoes. I couldn’t believe the number of people who were wearing cheap flip flops all day. This goes not only for mom, but for the whole family. Please don’t put your kids in cheap plastic flip flops unless you plan to carry them all day long. The other thing about Disney is that it is hot in Florida and very humid. If you’re not used to this type of weather, be prepared with moisture wicking clothes. If you sweat a lot, you may want to avoid having a heavy cross body bag that holds your shirt against your body. Disney has lockers that you can rent by the day. It might not hurt to pack a backpack and throw in a couple changes of shirts for the family. I did this, and it was so nice to be able to change from my sweaty shirt to a dry shirt before heading to dinner. One of the other things to keep in mind is that you will be getting on/off rides and some require you to lift your legs, straddle things to get in place. If you’re going the dress route, you might want to remember that. Otherwise, just be comfortable and have fun. Nobody, other than you, is paying attention to what you’re wearing.

  5. Jessica M.

    I second the hat suggestion, or even a visor if you like to wear your hair up (actually, Sally, do you have any suggestions for visors that aren’t frumpy??? I have long hair that I wear up most of the time, but also like hats to shade my eyes and face in summer…)

    Also, I like to bring a lightweight pair of pants – khakis, very light denim – or a knit maxi skirt. I’m not comfortable in shorts after more than a couple days without shaving, but I also find shaving to be a pain in the neck when I’d rather be out vacationing. The right leg-covering set of bottoms is almost as comfortable as shorts, gives better sun protection, and gives me a break from shaving.

    • Sally McGraw

      Hmm, I haven’t looked into visors myself! A quick search shows some interesting options from Hat Attack and San Diego Hat Company … not super cheap, but check 6pm for sales.

      Anyone else know of good visor options?

  6. Jennifer

    If you’re not used to the tropical sun, be extra generous with the sunscreen on the tops of your feet. Sunburns there are awful. And walking around with napkins tucked under your sandals to protect your crispy feet is probably not the fashion statement you want to make. (Not that I’ve ever had to do that or anything. 🙂

    You will be hot at Disney so definitely dress for maximum comfort. Most people dress very casually. And you will be outside most of the time so think about the effects of sunlight, wind, and as an earlier commenter mentioned, water on your clothes. You will spend most of your time standing or walking. Be sure your shoes are well broken-in for your trip. And bring some moleskin and a little blister first aid kit just in case.

    Not a fashion tip but if you’re traveling with children and you’re staying close by, go back to your room for a “nap” after lunch. You may be inclined to stay at the park all day in order to wring as much value out of the money you’re paying for this, but you’ll be fresher and better able to enjoy what you’re doing if you take a break.

  7. blair

    Why didn’t you ask a mom blogger to do a guest post about this? You used to do guest posts on topics where you had no experience, yet you start off the post saying that you have no experience in either of the things Ursula’s asking about and then go ahead anyway.

    Nothing in here takes into account the amounts of stuff kids need over an all-day outing (snacks, water, diapers, sunscreen, bug spray, someone to hold the things they’re sick of, hats, band aids, bags for wet clothes, distractions for when they’re bored, etc); the different types of clothing you need when your kids are at different ages (low-cut tops when you’re still nursing, dresses when they’re little enough to be carried so no one’s sitting on the waistband of your shorts all day, no necklaces when they’re at a grabby stage, clothes that are more comfortable under a baby carrier, etc); or even the numerous trends happening right now that make dressing stylishly for outdoor events easier than ever (sporty luxe), oversized everything, comfort-forward choices, etc).

    Ursula, my main piece of advice is this: wear a backpack. You know you’ll be carrying a lot of stuff, and after years hauling a diaper bag or a huge purse, having the weight distributed evenly across your back is luxurious.

  8. Natalie Wright

    Quick-dry clothes! Especially if you’re going to Disney World in Florida, where you’re likely to get caught in at least a couple afternoon rainstorms. And if your kids drag you on Splash Mountain, you’ll be thrilled if your clothes dry in 30 minutes. Athleta, Title Nine, and REI have adorable dresses in quick-dry material. I find these great for travel in general, because they can be washed in a bathroom sink and are ready to wear again within a couple hours. My quick-dry dresses are my go-to for almost any outdoor activity in hot weather.

  9. Andrea

    I am a *huge* fan of Eddie Bauer’s Travex line for travel in general. Most of the items have some stretch, they all wick wonderfully and dry in a flash, and are usually made of a high-SPF fabric. The fabrics are super lightweight, too, so they pack very easily. I prefer their skorts to shorts, even; with the stretchy fabric and attached under-short, I have both hiked in them and worn them out to dinner. Sizing can be a bit inconsistent, but that’s the only downside I’ve found. (And no, I don’t work for them!) 🙂

    Love Keens as well, especially those you can wash in the washing machine. I find their arch support to be enough, and I’ve spent entire days on my feet in them without any trouble.

    Also, I find a good sports bra to be absolutely necessary for my DD girls. Especially if there are any theme park rides involved. But even if not, they wick moisture so much better, and I find the extra support over a long day of moving around to make a huge difference. Big fan of Title 9’s “3 reasons” bra; I can wear it under most tank tops (that have wider straps) without any trouble.

  10. Galena

    I have family that lives in Orlando so we do the amusement parks quite a bit when we visit. (And I also live near Cedar Point which is the next best thing for rollercoasters.) Through trial and error, I find myself more comfortable in a closer-fitting just-above-the-knee knit skirt rather than an a-line or other floofy cut because I don’t have to worry about winds giving me a Marilyn Moment, but I still get the nice cooling effects that wind provides. I am also able to arrange the skirt easily on rollercoaster seats so I don’t show a crazy amount of leg or have issues with the fabric not having enough give to sit comfortably with the seat harnesses. Shorts ride up and chafe on me more often than not so I tend to avoid wearing them if I can get away with it. Then I just wear a casual knit tank top that doesn’t show sweat stains (patterns are better for this than solids, or darker colors if you prefer solids). You could also accomplish this with a tank dress that’s a closer fit. I don’t think I look too-dressed-up at all. I have flat feet so I am most comfortable in flats/sandals, but I wear a pair that are highly-broken-in and well-tested. If I wear flats/sandals that don’t have straps to keep them on my feet, I just take them off and sit on them when I go on rollercoasters that have dangly-feet seats.

    For reference, here’s a photo of myself and my husband at Universal Studios: If you look at the picture, you’ll also notice we’re wearing hats. I HIGHLY recommend at least having one with you, even if you don’t wear it all day. If you get a crushable one, you can shove it in your purse/backpocket/under your shirt (if you’re purse/pocketless) if you go on a ride or get tired of wearing it. Mine was under $15 at JCPenney, is crushable, a bit bigger than my head, and is a wide weave so I still got breezes on my head. It actually kept me cooler because it protected my face and neck and some of my shoulders. And since it was a bit big, it didn’t give me hat hair. An unexpected side bonus is that there are not that many people wearing hats (shame on them) so it is MUCH easier to pick out other members of your group from a crowd if you get separated at all. If you don’t wear a hat, make sure to sunscreen your ears and the part of your hair! Ear sunburns feel almost as terrible as feet sunburns.

    As much as possible, forgo a heavy face of makeup. You’ll look and feel worse when you’re sweating and it’s melting off your face (it is seriously a gross feeling) than you would if you were barefaced. I just wear my SPF foundation (which can also be layered with regular sunscreen) and a little bit of waterproof eyeliner/mascara. A setting spray keeps things in place as much as possible and feels cool and refreshing on my face. I also pack oil-removing shine sheets (Neutrogena and Clean&Clear are cheap and effective) to help desweat myself without messing up what little makeup I’m wearing. I can also reapply sunscreen throughout the day with no problems this way.

  11. Kate McIvor

    Thank you Sally! I’m getting ready to pack for a trip to rural Maine and Washington, DC. I think I know what to pack now. 🙂

    • DorothyP

      DC is very humid in the summer, and while there are plenty of tourists in shorts and tshirts, the museums and public buildings are very chilly (AC on full blast) so you might want to have something light with long sleeves.

      • Galena

        When I was in DC in the summer my solution was to bring a pashmina–it folded up small in my purse (or I could loop it around the strap if space was really an issue), and it kept me warm when I wrapped it around my shoulders in the high-AC buildings.

  12. Sally McGraw

    Hi Blair! You may have noticed that I asked for input from parents in the comments, as you’ve done here, and I appreciate all the relevant information the community adds to posts like these. I also am not long-waisted, plus sized, or over the age of 40, but readers still ask for my input on style questions that are specific to those groups. And I do my best to give it.

    The last time someone had a mom-specific request, I asked a guest poster to address it and readers took issue with virtually all of her suggestions. So I tackled this one myself as best I could!

    Finally, family vacations are taken with children of all ages, including ones who are capable of hauling their own stuff. Ursula’s question was about her own style, so that’s what I focused on.

    • Angela Denker

      I have a 2-year-old and thought you covered the bases just fine! Cross-body bags are great. In my opinion much more stylish than a backpack and actually more comfortable too (for me).

      Related to this I would be interested in a post on summer hats and where to look! I always check out Target but would like more options … Thanks!

      Oh, and I’m not a fan of their CEO, but I would probably wear Lululemon pants and a Target short sleeve wicking top for a Disney trip 🙂

  13. Sharlene Fye

    Been there several times in July, can be hot and sweaty because of the humidity and yes, it can rain the afternoon (nice time to take a break back at the hotel). If you go for the wet rides something that dries quickly. I have also used glide (used by runners) so you cut down on the chafing. You are going to walk a lot. I always use a fanny pack so my hands are free. Lots of sunscreen. I wear a hat too and had the kids wear one. Here is a tip to save money on drinks, ask for ice water at the restaurants and it is free. Usually the same size cup just ice and water. Also, you can order food without the sides (like fries) and just pay for the sandwich, saves a little money. Then use the condiment bar to create a salad with your sandwich. Cosmic Rays has amazing sauteed mushrooms.

    • JB

      I use the ice water trick in hotels too. Go to the bar and ask for ice water and they will give it to you for free, and if you’re staying at the hotel you can take it to your room. Saves a lot on bottled water!

  14. Ginger

    If you’re staying at the Resort don’t forget that the motels all have themed pools with lifeguards and shallow ends so kids can play.

    A dip in the pool after a long day is wonderful, gets kids cleaned up and relaxed for bedtime.
    Take pool shoes, your suit and a shirt or cover-up to wear on your walk to the pool.
    Don’t fret – you will not be the only person who isn’t very tan or who has a little jiggle here and there – and enjoy a dip at the end of the day.

  15. debbahs

    We just got back from our 4th trip to DisneyWorld a few months ago – great article and comments – I agree with what everyone else has said about the importance of great shoes, sunscreen, hats and COMFORT.

    I, too, am not a fan of shorts at ANY time, so I tend to go the casual skirt/dress route all summer long. It’s just more comfortable, and IMO, easier to dress up or down, which can be great when you’re at a place like WDW where you can ride a rollercoaster in the morning and end up at a nice restaurant for dinner, with no chance to get back to the hotel and change (my first trip it was surprising to me how HUGE WDW is and that it can take an HOUR to get back to your hotel depending on what park you’re at – for most parks there’s no just “heading back to the hotel for a quick change” that makes sense).

    When I know I’m going to be heading to a nice dinner without the ability to go back to the hotel, I will sometimes pack a nice pair of sandals and scarf/jewelry to dress up my “uniform” of casual skirt and t-shirt.

    In addition to the suggestions provide below, I’d make 2 specific recommendations from much trial and error on the shoe and bag front.

    I LOVE LOVE LOVE these Ecco MaryJanes ( – they are supremely comfortable and yet look stylish with a skirt. I have worn these all day at the parks with no problems with blistering, pain, swelling, etc. I’m on my second pair I love these so much and now that my daughter’s feet are entering women’s sizes we’ve ordered her a pair as well.

    As for bag, I’m a huge fan of the Yens Fantasypack ( – it’s small yet surprisingly roomy (I can fit 6-8 bottles of water plus my pared down touch-up kit (contact drops, sunscreen and lip balm), phone and other misc. necessities. What’s best about this though is the cell phone pocket on the FRONT, so you’re not doing contortions or taking off your pack every time you want to check the wait time on your favorite ride or make a dining reservation with the Disney apps (which is surprisingly frequent for our family anyway).

    Have a great time! Disney truly is a magical place!

  16. whitherwander

    I tend to regard amusement parks as outdoor endurance events and dress accordingly. If you’re worried about hitting the function/form sweetspot, aim for simplicity and colors that make you happy. Choose silhouettes that are easy for you to wear and don’t involve fussy belting or layering or (ugh) strapless bras. Pick clothes that skim your body a little loosely so that they are cool and don’t bind or make you self-conscious. I’d also suggest that if you wear make-up, keep it minimal to reduce smearing. Lastly, I always wear a sunhat, both for practical reasons and because it instantly upgrades summer outfits without looking like too much. Best is something with a nice wide brim that is crushable for packing and for stowing on any really crazy rides. Try the Village Hat Shop (online), which carries many brands at various price points.

  17. Kacie

    Oooh! We were just there in April. So fun! There is a blog called Disney Tourist Blog that is awesome, and it’s a husband and wife team. The wife has fantastic style and has written a few posts specifically about it. She often wears lightweight dresses, smart shoes and also carries a LeSportSac. They have a few Disney-related designs that look great.

    Honestly I think smart shoes are the most important thing. We are talking 7-10+ miles of walking a day and no I’m not making that up.

  18. oohlookasquirrel

    This was great to read. I’m in the process of packing for a trip to Italy. I live in skirts and dresses and I was all set to pick footwear that was pretty and sort-of comfortable, but you’ve talked me into comfy sandals and converse for at least 90% of the trip. It didn’t occur to me to pack my footwear first, but you’re absolutely right. I’m going to have a terrible time walking around Italy if I have blisters, even if I look terrific. My second consideration, after footwear, will be about required undergarments. I’m trying to minimize the amount of time I will spend sweating in bras.

    Galena, you’re completely right about skirts at amusement parks. I suffered in shorts for so long because I thought people wearing skirts on coasters were just asking for trouble, but you are so right. It can definitely be done.

  19. Jessica

    Hi Sally, I was just in the Dells last weekend! I wore a pair of denim shorts, a cute, flowy tanktop and comfortable sandals (and took along a cardigan since it can get chilly if you’re hanging out on the river). I found this outfit to be quite stylish, comfortable, and easy! And I have to say, wearing a loose tanktop is a good idea if you plan on eating that yummy Wisconsin Dells fudge!

  20. heather

    Ever since I discovered how to wear pashimas and shawls, they’re my go-to for any warm weather vacation. It’s so great to be able to cover up from the sun, add varying amounts of color and pattern to neutrals and have a soft, flexible garment on hand. I have them in linen, cashmere, lighter wool, cotton and silk. My favorite metallic silk pattern can really dress up a plain outfit and the chambray cotton pashima dresses down my packable black bamboo dresses (which can look like cocktail dresses by themselves). I have had good luck finding them at flea markets and thrift stores- I don’t think I’ve ever paid more than $25 for one.

  21. Claudia Gray

    Only things I have to add:

    For my money, cross-body bags beat fanny packs every time. Fanny packs are useful, but they invariably look awful, whereas cross-body bags can be both practical and attractive. Also, fanny packs don’t come in super-huge sizes, but you can get a good-sized cross-body bag; get a bag with compartments and you may find it much easier to get to sunscreen/band-aids/the phone/ etc. swiftly. Finally, you can take turns wearing the cross-body bag with your SO, a friend along for the day, or an older, responsible child, so that you’re not the only one with the weight (where this would apply.)

    If you’re in the sun, consider a hat! Look for a soft collapsible one so you can fold it in the bag during rides. I have a few that are both practical and very cute.

    I don’t even own non-workout shorts, because I find skirts far cooler and more comfortable for hot-weather wear. (And at Disney, either one, I assume that’s what you’re dealing with this time of year.) But if you’re going on rides, make sure your skirt is either a close-fitting knit skirt or an A-line out of a sturdier fabric (like khaki or denim) that will protect you from flashing people on the loops! Both of those fabrics are also easy to match with virtually any color or pattern of the tops you might have brought. And, as another person said, skirts are easier to dress up; put on a fresh, slightly dressier top and a bigger piece of jewelry, and you will look great when you go out to dinner.

    Comfy shoes are a must, but regardless, consider bringing some of the band-aid wax sticks you can apply to your feet to reduce chafing. I have warded off many blisters that way.

  22. Susan

    I second the comment about quick dry clothing. And also this relates to footwear. Some shoes begin to hurt if you are walking and you get caught in a downpour. Also, pack an emergency poncho or two. You can buy them for a few dollars.

  23. ekaren

    I live in Florida and was at Disney’s Magic Kingdom just last Friday. A few things that worked for me: I wore sneakers, and I am not a sneaker-wearer. But between the 18,000 steps logged on my FitBit that day and the torrential downpour with subsequent deep puddles, I had no regrets with my choice of footwear. Speaking of rain, we tried to wait it out but finally ended up buying rain ponchos at the partk ($17 for 2). They are ugly, but do allow you to continue on with your day. Better to bring than to buy. Lastly, I wore a small cross-body bag rather than carry my usual, larger purse. I realize that with kids you may have a lot of things to carry, but you’ll find that since Disney is an older park, many of the rides have smaller seats with very little room to spare. My 6’4″ husband had trouble enough folding himself into some of the rides, let alone trying to squeeze carry-ons in as well. Travel light as best you can! And have a wonderful time!

  24. Thursday

    I’ve done a fair bit of backpacking/long trips and comfy, supportive footwear is the most important thing in my mind. When you spend weeks on your feet sightseeing, ill-fitting and flimsy footwear can make you miserable. My most recent pair of walking shoes, which did a great job of walking me round the US and Canada on my last seven week holiday were Keens. I pack a second pair of lightweight shoes – flats or sandals – to give my feet a break and for a more dressier option.

    For humid climates, there’s nothing like natural fibres.