What to Wear When You’re Retired (But Still Want to Look Cute)

Photo by Lucretius Mooka

Let’s be honest retirement is supposed to be relaxing, but figuring out what to wear every day? Still kinda stressful.

You’re not dressing for the office anymore. You don’t need heels, slacks, or anything that requires ironing. But you do still want to feel like yourself. Put-together. Comfortable. Stylish—without trying too hard.

If your closet feels a little too “before times” and not enough “this new chapter,” this post is for you. Whether you're heading to brunch, running errands, hanging with your grandkids, or hopping on a plane for that long-overdue trip—these outfit ideas were made for your real life.

They're comfy without being frumpy, pulled-together without being stiff, and every single one passes the “I can actually move in this” test.

Let’s get into it.

Not sure what to wear lately? We made something just for you: 60 outfit ideas for women over 60—no frump, no fuss, just real style you’ll actually wear. Send me the list!

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1. Soft Button-Up + Stretchy Trousers + Loafers

This is your “I’m running errands but still want to look pulled together” uniform.
A soft button-up (think cotton, linen, or a lightweight poplin) gives structure without stiffness, while stretchy pull-on trousers keep it comfy. Add a pair of cushioned loafers, and you’ve got an outfit that says, Yes, I’m retired—and yes, I still look good at the pharmacy.

Stretch Cotton Poplin Boyfriend Shirt

$50

Express

High Waisted Relaxed Trouser

$88.00

Rothys

The Double Bit Driver

$199

Style Tip: Try a button-up in a color that brings out your eyes or a small print you love—just enough detail to feel intentional.

2. 3/4 Sleeve Knit Top + Linen Pants + Slides

You’ll wear this one on repeat when it’s hot but you still want coverage.
Linen keeps you cool. A knit top with elbow-length sleeves gives you the arm coverage you like without being bulky. And slides? They’re the real MVP of retirement footwear.

Express

Fitted Ribbed Boat Neck Elbow Sleeve Tee

$28.00

Amazon

Linen Pants Wide Leg

$36.99

Amazon

Cork Footbed Slide Sandals with Arch Support

$39.99

Style Tip: Look for linen pants with a wide leg and a soft waistband—your future self will thank you.

3. Layered Tank + Open Cardigan + Relaxed Jeans

For those “grab lunch with a friend” or “Home Goods run turned into a full afternoon” kind of days.
Start with a well-fitting tank (yes, you can still wear tanks—just layer strategically), then toss on a lightweight cardigan or duster. Pair with your most comfortable relaxed jeans and you’re good to go.

Amazon

Double Layers Blouse

$19.99

Amazon Essentials

Women's Lightweight Open-Front Cardigan

$17.10

Amazon

Levi Strauss Signature Gold Women's Heritage High-Rise Loose Straight

$32.31

Style Tip: Choose a tank with a higher neckline and thicker straps—it’ll give you better coverage and feel more polished under layers.

4. Tiered Midi Dress + Light Shrug + Flat Sandals

When you want something breezy but not shapeless, a tiered midi dress is your answer.
It floats over the body, gives you room to move, and looks great with a cropped shrug or knit topper. No shapewear, no stress.

Express

Mixed Media V-Neck Sleeveless Drop Waist Midi Dress

$98.00

Amazon

Lightweight Open Front Shrug Bolero Sweater

$19.98

Amazon

Women's Slide Sandals

$38.99

Style Tip: A low wedge or embellished sandal instantly makes this feel like “I got dressed today” energy.

5. Lounge Set (That Doesn’t Look Like Pajamas) + Simple Jewelry

Retirement means you can lean into comfort—and do it with style.
Look for lounge sets in soft knits or marled fabrics, with just enough shape to wear outside the house. You’re aiming for “put-together at home,” not “just rolled out of bed.”

Amazon

Two Piece Matching Lounge Set

$35.99

Style Tip: Add a chunky bracelet or a long pendant necklace for instant polish.

6. Boatneck Tunic + Cropped Pants + Comfy Flats

Boatnecks are must have—they elongate the neckline and flatter almost every body shape.
Pair yours with cropped pants (pull-on or structured, depending on your mood) and a sleek flat. Easy, effortless, and elevated.

Amazon

Boat Neck/V Neck Dolman Top

$18.75

Amazon

High Waisted Flare Jeans Cropped

$46.99

Amazon

Wide Loafers Casual Slip on Flat Shoes

$34.19

Style Tip: If you don’t love your midsection, choose a tunic that hits mid-hip with a slight A-line shape.

7. Wrap Top + Knit Midi Skirt + Low Heeled Mule

This is your “I have a casual dinner but still want to feel pretty” look.
A faux wrap top defines the waist without clinging, and a knit midi skirt moves with you. Low block heels or mules give you a little lift with none of the pain.

Amazon

V Neck Wrap Sweater

$39.89

Amazon

Long Satin Skirt

$34.99

Low Heels Block

$29.99

Style Tip: Choose one printed piece (like a floral wrap top or a striped skirt) and keep the rest neutral.