This post has been updated as of February 2026 to reflect current styles, updated links, and what actually works now—not just what looks good in perfectly filtered vacation photos.
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If you’re anything like me, the second your flight is booked, your brain immediately goes into vacation mode.
Dinner reservations? Done.
Spa appointments? Obviously.
Mentally checking out of real life? Already happening.
You’ve been dreaming about this trip for months.
Beach sunsets. The smell of sunscreen and salt air. The sound of waves crashing. Jimmy Buffett playing somewhere in the background. You, sitting poolside, fully relaxed.
Lucky you.
You’re ready.
Almost.
Because then comes the part nobody puts on Instagram.
You actually have to get dressed for it.
And when you wear AFOs (leg braces) like I do—live with a disability, mobility
challenges, and a 55-year-old body that’s now negotiating with gravity along with foot drop—resort wear is no longer just about style.
It’s also about strategy.
What’s easy to get on and take off without turning it into a full upper-body workout.
What won’t make walking through sand feel like you’re dragging two elephants behind you.
What won’t make navigating a wet pool deck feel harder than it already is.
What won’t make you start strong at dinner and slowly unravel by dessert.
What won’t make you feel like you’re managing your outfit instead of enjoying your life.
But here’s what I’ve learned after decades of trial, error, and more than a few “what was I thinking?” purchases:
Resort wear isn’t about hiding.
It’s about choosing pieces that work with your body—not against it.
And in 2026, that’s finally getting easier.
Resort wear has evolved. It’s less about perfection and more about ease, versatility, and confidence. Pieces that move with you. Support you. Forgive you. And don’t require constant adjusting, pulling, or quiet suffering.
Because when your clothes work, you stop thinking about them.
And when you stop thinking about them—that’s when you actually relax.
And at 55, relaxing isn’t optional. It’s the whole point.
Here’s how I approach it now.
SO, WHAT’S RESORT WEAR ANYHOW?
You’ve got a cold drink in your hand. The air is warm. The light is softer somehow. Your shoulders finally drop an inch.
That’s resort energy.
It’s not about dressing like a different person. It’s about dressing like yourself… just with better lighting and fewer emails. Lightweight pieces. Nothing fussy. Nothing clingy. Things you can pack without a strategy meeting.
Breezy cotton. Real linen. Fabrics that don’t stick, tug, or require adjusting every five minutes. Tropical prints if that’s your mood. Color if you’re feeling it. And yes — black still works anywhere. Always.
Resort wear should feel easy. Easy to put on. Easy to move in. Easy to live in.
And when you wear AFOs or live with any kind of physical difference, “easy” isn’t a luxury — it’s the standard. Clothes that cooperate. Clothes that don’t fight your body. Clothes that let you sit, stand, walk, roll, scoot, stretch, and just be where you are.
Here’s what that looks like in real life:
Pull-on linen pants that look polished but feel like pajamas.
Maxi dresses that go on in seconds and don’t need babysitting.
Simple jumpsuits that do the styling for you — one piece, done — and double as a swimsuit cover-up when needed.
Trendy is optional.
Comfort is not.
The best resort wear isn’t about what’s “in.” It’s about how you feel in it — comfortable, confident, and free enough to actually enjoy your trip.
Because that’s the point.
Now, here are some of our best resort wear tips for actually enjoying your vacation (not just packing for it)… and of course, a little shopping inspiration too.
If you’d rather skip straight to the good part, you can head right to the shopping links here.
Pro Tip #1: Stop saving your “good outfits” for later
Wear the dress.
Wear the sandals.
Wear the bright color.
You are literally at a resort. This is the moment.
Resort wear is one of the few times in life where ease and effortlessness actually look better than trying too hard.
And here’s the irony:
The more comfortable you feel physically, the more confident you look emotionally.
Confidence isn’t about having perfect legs.
It’s about not apologizing for the ones you have.
Pro Tip #2: Maxi Dresses Are Still the Easiest Win. Always.
If there’s one thing I reach for over and over on resort vacations, it’s a maxi dress.
Not because it’s trendy. Not because it’s flashy.
Because it works.
Maxi dresses don’t fight your body. They don’t compete with your braces. They don’t require constant adjusting, pulling, or negotiating.
They go on easily. They move easily. And they somehow make you look put
together—even when you’ve made very little effort.
At 55, that’s the sweet spot.
Look for fabrics that are soft and breathable. Nothing stiff. Nothing clingy. Nothing that makes you feel like you have to stand perfectly still for it to look right.
Adjustable straps are helpful. Stretch is helpful. But honestly, the biggest factor is how it feels when you put it on.
If you forget about it within five minutes, it’s a winner.
If you’re constantly thinking about it, it’s not coming on the trip.
Pro Tip #3: Your Sandals Can Make—or Break—Your Vacation
Shoes matter more than anything else.
Not just aesthetically—but emotionally.
Because when your shoes don’t work, nothing works.
Walking through sand is harder. Pool decks feel riskier. You move differently. You think about every step.
The right sandals change that completely.
They provide stability. Support. And most importantly—confidence.
You stop thinking about your feet.
And when you stop thinking about your feet, you start enjoying where you are.
Look for sandals with adjustable straps, supportive soles, and enough structure to accommodate your brace comfortably.
The right pair doesn’t just complete the outfit.
It changes the entire experience.
Pro Tip #4: Accessories Are An Easy Way To Show Your Personality
One thing I always tell women: don’t underestimate accessories.
When you have a disability, it’s easy to feel like that’s the first thing people notice. So why not give people something else to look at? A bold necklace. A stack of bracelets. A great bag. Accessories instantly add personality and they start conversations for you. People comment on the color, the texture, the statement piece — and suddenly you’re talking style, not braces.
And practically speaking, I only choose pieces that work with my hands. Magnetic clasps, stretchy bands, easy closures. If it’s hard to get on, I won’t wear it. Style should feel expressive, not exhausting.
Your braces might support you. But your accessories tell people who you are.
Pro Tip #5: Pull-On Pants & Easy Jumpsuits. Trust Me.
Lightweight pull-on pants are the most underrated piece in a resort suitcase.
No buttons. No zippers. No standing there in a humid bathroom trying to wrestle yourself into something “structured.” You step in, pull up, and you’re dressed. That’s it.
They’re breathable. They move. They don’t grab your thighs or cling in weird places. They skim. And at this point in life? Skimming is a gift.
They work with braces. They work with swelling. They work when you’re sitting longer than planned at dinner. They just… cooperate.
Throw on a tank. A tee. A loose button-down. Add a sandal and an earring and
suddenly you look like you tried.
And an easy jumpsuit? Same vibe. One piece. No math. No “does this go with this?” It’s the adult version of getting dressed in 30 seconds and somehow looking pulled together. I especially love one that can double as a swimsuit cover-up because I am not packing extra outfits if I don’t have to.
Vacation clothes should not require effort.
They should let you enjoy the vacation.
Click Here To Shop Our Favorite Pull-On Resort Pants & Jumpsuits
Pro Tip #6: The Goal Isn’t to Look Perfect. It’s to Feel Free.
This is the biggest shift that’s happened for me over time.
I used to dress to hide.
Now I dress to live.
Some days I show my braces. Some days I don’t.
Not because I’m hiding—but because they’re no longer the headline of my life.
They’re just part of how I move through the world.
And the right clothes make that movement easier.
Because at the end of the day, resort wear isn’t about impressing anyone else.
It’s about being comfortable enough to forget about your clothes entirely.
And finally, just enjoy where you are.
Final Thoughts
Resort wear isn’t about perfection.
It’s about ease.
It’s about choosing clothes that allow you to live your life fully—without distraction, discomfort, or compromise.
At 55, I’m not dressing to impress strangers.
I’m dressing so I can walk comfortably, enjoy my vacation, and stop negotiating with my clothes.
Because the right clothes don’t change who you are.
They let you be yourself—fully.
Click Here To Shop Our Favorite AFO-Friendly Resort Wear Collection
Xoxo
Lainie
Curious about the sandals with AFO’s. I try to find removable insoles, but the sandals you show don’t seem to have that feature. How to you prevent the AFO’s from slipping around or being rocky on molded footbeds?
Thanks so much for reaching out! I typically try to find sandals with removable insoles & footbeds for those who wear bulkier AFOs. For example, this is one of our partner brands. https://www.revereshoes.com/collections/afo-friendly-sandals?ref=nz6y3ukurq
If there are sandals that have molded foot beds, that is a mistake on my part. When sandals do not have removable insoles, I’ve recommended them because they are either completely or mostly flat. To keep AFOs from slipping, you can try using a no-show grippy sock on the footplate, or double sided tape/velcro tabs. Hopefully this is helpful. 😀Lainie
In sandles that are open or backless how,do I keep my foot plate from sliding forward or backwards. It is a allard 2.0 it looks awful sticking out.
Hi Diana, have you read this post? https://www.trend-able.com/7-hacks-for-orthotics-afos/
I hope it helps!
My “walking cradles just came in the other day! Next in the list….the white elastic waist jeans!! Thanks so much for sharing??
Thanks for reading & taking the time to let me know! It means a lot. The white jeans are fabulous ??
I love your sense of style!!! I wear lots of wode leg pants and am tired of my sneakers with them since I love to dress up. I’d love some sandals but I don’t see any here that have a removable insole
Is there a way to wear an afo in a shoe without a removeable insole? Thank you and enjoy your travels!
Thanks for reading Denise and for your sweet message! It totally depends on the type of AFO you wear. I can wear white shoes that don’t have a removable insole or foot bed depending on the shoe. If you want to send me an email at info@trend-able.com I’m happy to recommend some sandals that will fit your braces specifically
Hi Lainie, what an awesome styles of outfilts you shared in your blog. I like those brown color of footwear, and I am willing to buy same type of footwears for me. Thanks for sharing.
Hi Shirley,
Thanks so much. I’m glad you like them. I hope they work out for you ?
Can you wear the Naot pixie sandal with out your brace…if so how do you do that. I have Drop foot (left) and balance issues. I’m 76 but love fashion. I don’t hide my brace but seldom go out with out and it’s a drag as I love to dress up.
.
Hi Sandra,
I wear my braces always so every shoe pictured are worn with my afos. Obviously, they can also be worn by people without but these are shoes that fit with as well.
I am able to wear a small wedge with my afo. I was not able to in previous ones. Does this answer your question ? Feel free to restate if I didn’t ??