Casual Style for Women Over 50: Running Errands

I try to run most of my errands during the week. Doing it on the weekend means hoards of traffic, more crowds and long lines. I like to be comfortable so reach for casual clothes that give me a stylish look. You don’t have to dress up to look stylish, but you need to leave your slippers and rumpled clothes at home.

Welcome to this week’s Hit Your Style Sweet Spot, my weekly collaboration with Pamela Lutrell from Over 50 Feeling 40!

Style Sweet Spot

Your Style Sweet Spot is when you know your appearance is sending the message you intend and feel confident you look your best. Last week Pam and I shared how we dressed to attend a graduation…this week we’re dressing for a casual day, running errands.

Casual to me, is not synonymous with sloppy. Unlike the lady I spotted at Costco today… wearing her slippers! It means comfortable, easy to wear clothes that are quick to pull together and require no further thought during my day.

Running errands mean my shoes must be very comfortable.

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Comfort means flat shoes and jeans with stretch. These jeans from Chico’s have become my favorite.

I always carry a tote bag, to hold small purchases, when I'm running errands.
Yoshi Tote Bag by Jutta Neumann  from Artful Home

I like to pop a small handbag inside a tote bag which can hold small purchases and things I need while racing around. It always holds my water bottle and usually a protein bar. This gorgeous tote elevates the look of everything I wear it with.


A classic white shirt with jeans and leopard shoes is casual and chic for running errands

An oversized, crisp white shirt is comfortable and fresh looking. Yes… it wrinkles by the end of the day…but that doesn’t impact its charm for me. This one is on sale at J Jill here but only in color, not white.

A few great accessories dress up casual wear for running errands

A small hat and some great accessories polish off my simple outfit and keep it from looking plain.

Here’s how I hit my Style Sweet Spot for running errands. I feel stylish, comfortable and well dressed enough to run into anyone during the day.

Now lets pop over to see how Pam dresses to run errands.

What do you wear to run errands?

xo Jennifer


Disclosure: Artful Home supplied my leather tote, the opinions are my own. Affiliate links in this post may generate income for AWSL. Please see my complete disclosure statement here.





  1. Came by way of Pinterest and though this is an old post; just wish to compliment you on your fashion savvy. In respect ‘what do I wear while running errands’; actually very similar to what you do however its been ages since I’ve worn a hat (but do love them). Regarding necklaces; admire yours however I often choose much longer ones to get double duty out of them. i.e.: To be worn long or double wrapped (to shorten). The latter which sometimes requires the easy application of a necklace extension to make it work. Wonderful and informative blog!

  2. Jennifer, this is such an easy polished look! Your accessories definitely elevate a basic white shirt and jeans to a completely fabulous outfit! The leopard flats are adorable and I am swooning over the metallic tote! However, I do so hate when my crisp white button downs turn to a wrinkled lint-covered mess by the end of the day!

    Perfect errand running outfit, for sure!


    1. Yes, they can look less than crisp at the end of the day…but I still love classic white shirts!

  3. A great simple very classic look. You look great. Now that summer is here I too like to sport a hat. I do get hat hair so I just don’t take it off while running errands.

  4. That’s very cute. I get the jeggings from Costco that looks like jeans. I think they are about $15. I pair them with an Everlane t-shirt and jewelry and a cashmere boyfriend cardigan if it’s chilly. I’m ready to go anywhere!

    1. I love Costco! I haven’t noticed their jeggings! Thanks Jen, I’ll be on the lookout for them.

  5. My style exactly,but no hat for me. They suit you beautifully but make me look like a mushroom!! I sometimes add a French market basket instead of a tote.

  6. Love the whole outfit – cute shoes too. Are they comfortable? Flats commonly don’t support my feet, and my legs feel so tired at the end of the day if i wear shoes that are not really well designed – which usually means – not so attractive. It’s a real difficult issue since I am very functional – even though i want to also be fashionable. Do you have a favorite brand? I love your outfits!

    1. I have some cork orthotics I move from shoe to shoe. Generally I’m most comfortable in flats that have cushioned soles. My very favorite are by Eileen Fisher because they combine comfort and style.

    1. I see women in heels running errands and wonder how they got lucky to have their feet can tolerate it! I envy them but know it’s just not an option for me. Leggings yes!! So comfy.

  7. You can’t go wrong with classic white shirt and jeans. I’m wearing my own version of that today. Love the addition of the hat.

  8. Hi, I like a white shirt, but don’t like my bra showing through it, what can I do about it?

    1. I wear a nude bra under white. Sometimes I will wear a cami. But the trick is the nude. Finding your nude, not just a generic tan color.

  9. You look great. I think that a key element to any stylish is the intent which you have achieved by your accessories. It’s easy to grab a pair of favorite jeans and clean top but having ‘go with everything’ accessories make getting ready to take on the day a snap.

    1. So true Rena! Accessories are the finishing touch that makes all the difference in how an outfit looks.

  10. I have just discovered your blog and I love it. I have followed some other ‘over 50’ blogs and found their clothing selections are not even an option for me due to financial reasons. Thank you for providing classic, affordable styling tips!

    1. Welcome Pam. I do show all price points and you will see some higher priced items here too. I hope it will inspire women to take the styling suggestions and find them at their price, comfort level. With my husband retiring last month, my budget will change too! Of course I am very fortunate to be given some garments to share with my readers.

  11. HI Jennifer—love this outfit. Do you have a link for the blouse that you’re wearing? Does it require a tank or cami underneath and what is the fabric? I love those French Kande medallion necklaces, but haven’t purchased one yet because of the price. One day though. . .do they ever go on sale? Love your blog. Have a nice holiday.

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