What I Pack Now: Summer Vacation Outfits for Women Over 50
When it comes to summer vacation outfits for women over 50, I keep things simple. I’m not trying to reinvent myself on vacation…I just want to feel comfortable, look like I made an effort, and avoid dragging home a suitcase full of clothes I never wore. I’ve done that before, and all it taught me was that packing for “what if” rarely ends well.
These days, I skip the just-in-case extras and stick to the pieces I know I’ll actually reach for in breathable fabrics and shoes I can walk in. Nothing fussy, nothing that needs special handling, and definitely nothing that cuts off circulation after lunch. A small, dependable mix that helps me feel polished, even when the weather is sweltering.
Effortless Summer Vacation Outfits for Women Over 50
1. A Crisp Linen Shirt and White Pants Always Earn a Spot in My Bag
I always pack at least one lightweight button-down shirt in the summer, and linen is hard to beat. It looks relaxed, never fussy, and pairs effortlessly with white ankle-length pants for a look that feels crisp and classic. Slide sandals keep things easy, especially if you’ll be slipping them on and off frequently. This combo just works for me. It’s cool, classic, and always feels intentional without trying too hard. If you love linen, you may enjoy How to Wear Linen Without Looking Sloppy
2. The Outfit I Wear When I Don’t Want to Think Too Hard
I love a soft knit tank dress as an easy base for travel days. It looks a bit more elevated than pants and is actually more comfortable to sit in. I often wear mine with a classic denim jacket, which adds some structure and warmth without feeling too heavy.
A sleek leather sneaker (preferably one that’s already broken in) finishes the look and makes it practical for walking. I wear this kind of outfit when I want to feel slightly elevated but don’t want to think too hard about what I’m wearing. You may also enjoy How to Wear a Jean Jacket Over 60 And Still Look Current.
Shop Flattering Tank Dresses
3. Linen Blend Shorts + Light Blouse + Raffia Accessories
I know shorts are polarizing, and many women no longer wear them, but the right pair can be a great asset to a summer travel wardrobe. A longer inseam, a relaxed leg, and a linen or linen-blend fabric can make all the difference. Try wearing them with a soft blouse that adds some movement and looks more elevated than a tee. A raffia tote, a sunhat, and maybe even a woven belt will add texture and interest.
4. A Matching Set That Looks Effortless, Even When You’re Not
There’s something wonderfully low-maintenance about a matching set. Whether it’s shorts and a button-up or a gauze top with wide-leg pants, sets always look like you’ve made an effort, even if you haven’t. I tend to reach for soft cotton or gauze in summer, and I like keeping the accessories minimal, like a woven bag, leather slides, and simple hoops. The beauty of a set is that you can wear the pieces together or separately, which makes packing a bit more efficient.
5. The Maxi Skirt I Reach for on Warm Evenings
A floaty maxi skirt always feels graceful to me and hides my pasty white legs…while adding a touch of elegance. I look for one with movement, ideally in a breathable fabric and a pull-on waistband. I prefer solids, but there are lots of great prints available. Pair it with a close-fitting tank or shell so the silhouette stays balanced. I love to dress these down for casual days or up for a leisurely stroll after the sun goes down.
Shop Perfect Maxi Skirts For Summer
6. My Go-To Swimsuit Look That Works Beyond the Beach
I pack a swimsuit I feel confident in and a cover-up that can take me from the pool or beach to lunch or window shopping. A tunic or caftan in a gauzy fabric feels more refined than a basic tee and is much more modest. I always pair it with oversized sunglasses that cover my smeared or non-existent mascara, and flat sandals that are comfy on the feet. You may also like Best Tankini Swimsuits for Women Over 60 or A Complete Swimsuit Guide for Women Over 60
7. A Day Dress That Pulls Its Weight in My Suitcase
A casual day dress is one of the easiest pieces to pack, and it always earns its keep in my suitcase. I gravitate toward shirt dresses, simple cotton sheaths, or breezy midi styles. They take up very little room, don’t require much styling, and transition easily from morning coffee runs to afternoon sightseeing.
I like to keep the accessories simple with a neutral sandal that can handle a bit of walking, and carry a lightweight scarf that adds personality or serves as a shawl when needed.
Getting dressed on vacation should feel like a pleasure, not a chore. The key is to bring pieces that work together, feel good against your skin, and help you move through your day with confidence.
Do you have any favorite summer vacation outfits? Or a piece you never leave home without? I’d love to hear what works for you.
Thanks for reading, and be sure to wear what makes you feel confident.
Linen is lovely, but it packs terribly (and who wants to iron in a hotel room? If there even IS an iron.) And a white top can be a “one-wear” if it gets a mark. Why not a neutral or black/darker gauze or chiffon blouse? Those look great over a dress like a jacket, tied at the waist with a tank or even as a swim cover. And chiffon (not genuine silk chiffon) can be rolled in a literal ball in my suitcase and come out looking fine. Love the tank dress (I always pack those!) I was just away for 2 weeks and wore a black tank dress often, took different jewelry and belts like a chain one, casual brown leather one, and a big buckle fabric tie one and it felt like different outfits. Never sneakers for the somewhere warm…too hot to wear and take a lot of room in a suitcase. Flat leather walking sandals are better. (I can squish 3 pairs of flat sandals in the same space as one pair of sneakers ! Lol! I love shoes!) Love the midi length, but they’re not easy to find (especially without an ugly ruffle at the bottom.) I lean towards midi or knee, stretchy (no wrinkles!) pencil skirts. I have stretchy denim one that goes with everything. They suit my particular figure better and something like a black or white one can be casual with flip flops or dressy with cuter shoes (and the chiffon top!) Great article though! It makes me want to pack again and GO!
I thought I saw a link for slightly over the knee dresses. I prefer all my dresses from t’s to dinner wear to be over knee length or midi length.
I would appreciate any input you may have as I just don’t know where to shop for these. Also tops or dresses with built in bra support!
There are lots of knee length dresses around these days. I just saw a whole rack at JCrew Factory today!
This was a very helpful post. Thanks for putting the time in to help me plan my vacation packing.
Thank you for the great travel wardrobe ideas!
I’m slowly perfecting what goes on trips with me. I am a “classic winter” with gray hair so the last few trips I’ve only packed black, white and gray clothing with aqua as my accent color. Having a limited color palette makes sure everything goes with everything, so I’m packing less. This last winter I spent 10 days in Panama, half on a sailboat and half in Panama City, and even with needing two completely different wardrobes, it all fit in a carryon.
Brilliant Cathy!! You’ve got it down pat. And what an amazing sounding vacation!
I usually pack what I wear at home. I know my outfits and am comfortable in them. I always pack at least one dress and a new outfit suitable for the location and venue. My last two trips I wore everything I packed so I think I have it figured out. No more lugging home a big suitcase with unworn clothes. But, I still need more than a small carry on.
I only have a few things I reserve for vacations, and even those got worn a bit last summer
At age 78 don’t travel like I use to but feel your vacation guidelines are super for those who do. That being said though something I appreciated when I did; were garments that were easy maintenance as most destinations were that of warm or tropical weather with fabric preference being in a cotton or its blends. Also on the subject of footwear and not being a fan of sneakers/trainers (unless worn for athletics or home chores) I am still on the hunt for something similar to an older pair of Sketcher’s (called ‘Bikers’) that are slip-ons that are similar in design of a leather ballet flat but with a peep toe whose sole is a hybrid of a sneaker and when worn it is not unusual for someone to ask, ‘where I got them?’ -Brenda-
P.S.: At the time of purchase they only came in black but if I had realized the practicality of them I would have bought a few pair and would be dying them….☺.
Those sound great Brenda!
I love reading AWSL! I am an over packer as well but your post gave me some great tips on minimizing the amount of clothes and maximizing the look! My husband thanks you as well! Happy travels☀️
Husbands don’t always thank me for my advice 🙂
Love your picks Jennifer. If I still traveled, I would follow your suggestions.
We are leaving soon for a Caribbean resort vacation. What would be an appropriate outfit for a restaurant that is “smart casual?” It specifies long pants and collared shirts for men, but no guidance for women. Thanks!
A casual loose skirt and pretty blouse would fit the bill with upgraded accessories. Or a summer dress always works. Flowy pants and top too.
What great ideas!
I’m all about packing smart yet looking together
Thank you
Lovely vacation outfit options. I have been working on putting together a vacation wardrobe. I always pack a jean jacket and white denim pants. I recently bought a Quince navy linen dress to be my go to dress. I love the idea of a white linen button down shirt. One reader expressed concern about stains which is a good point. I will think some more about the color for the shirt.
I love when you show put together outfits. They always give me great ideas. Nowadays the one thing I make sure to bring are comfortable neutral colored shoes. Hopefully ones I can wear with everything. I don’t wear shorts but I do bring white jeans everywhere.
My neutral shoes now get worn not often than my black ones which is a big change from 10 years ago.
I love Laura’s scarf idea. I think I may try that this summer with a cornflower blue, white, khaki scarf I love. I tend to pack too many color ways. While I love having choices, it’s impractical and results in overpacking.
I do too.
This post is very helpful. I love the suggested outfits, something I often struggle figure out when packing. I live in southern California and many of these ideas work for everyday here.
Terrific Post!
HI Jennifer-this is a great article, full of wonderful ideas. This may not be a favorite with everyone, but at 63 y.o. I stopped wearing shorts some time ago, but I do love a skort. It fits in my wardrobe in place of the shorts.
Good morning!
I follow much of your tips on summer packing, except the white pants! I don’t allow room for more than three pants, and white just attracts dirt for me, meaning I’m often sightseeing and those places tend to be messy. I always end up sitting in something or dropping something on the white pants. White oante have kist their rotation in my packing! I substitute sometimes with a Khaki bottom. Thanks for your tips.
Good morning! Many people have an issue with white. I dare not say I haven’t because you just know that today, I’ll spill something dark on my white shirt :).
These outfits are spot on! Very modern classic. You’ve confirmed something I have noticed-Frank and Eileen get a lot of inspiration from LL Bean! (Though I thought that matching set was EF in Atlantis!) The Quince linen is good ladies!
Great catch Shari. Modern classics find much inspiration from brands we’ve known and worn for years!I love my Quince linen too.
I love the items you have posted. I pick a scarf (or 2) and build my packing list around it. Everything must go with the colors in the scarf. This insures that every piece mixes/matches. San Diego I went with Red/White/Blue. NOLA: Black/White/Red. 2 T-shirts, 1 button down, 2 Shorts, 2 Pants, optional skirt, A dress, Carry a jacket/sweater, My scarf, a purse, a carry on leather bag that doubles as a purse, optional bathing suit, undies & pjs, Baseball cap, sneakers, slides, flat closed toe. Check weather ahead of time to see if rainwear is necessary! This can last me a week or more. For me: Joggers are the only pants to wear on the plane (the bathroom is gross & I don’t want my pants to touch that floor! (I am over leggings – never wore them). Wear my bulkiest shoes, long sleeve t-shirt & jacket. Only wear inexpensive jewelry as I don’t want to be a target. Wishing you all fun and safe travels!!!
I agree about the pants issue on planes. Wide legs are a hassle and skirts are often the easiest for me.
Great summer looks 🏖️🌞