Casual Style for Women Over 50: Running Errands

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.

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

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.


This post may contain affiliate links which won’t change your price but will share some commission.


  1. mrsben2
    July 25, 2019 / 7:46 am

    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!

    • July 25, 2019 / 9:03 am

      Welcome, Brenda. I’m loving longer necklaces these days too!

  2. Shelbee on the Edge
    June 2, 2016 / 9:19 am

    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!


    • Jennifer
      June 2, 2016 / 10:30 pm

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

  3. June 1, 2016 / 5:31 am

    Very polished. A local store I often visit recently told me I was always “so pulled together.” Think that was a compliment. xoxox

  4. May 31, 2016 / 1:32 pm

    You look very stylish. Love the tote. I wear leggings and exercise clothes when I do my daily errands since I do yoga most days.

  5. May 31, 2016 / 8:24 am

    Love your style, this is a look that even i can pull off!

  6. May 31, 2016 / 5:56 am

    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.

  7. May 30, 2016 / 10:42 am

    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!

    • Jennifer
      May 30, 2016 / 9:58 pm

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

  8. Marilyn
    May 30, 2016 / 12:54 am

    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.

    • Jennifer
      May 30, 2016 / 9:56 pm

      I love French market baskets!! They’re a great alternative to a tote.

  9. Karen Leggett
    May 29, 2016 / 8:56 pm

    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!

    • Jennifer
      May 30, 2016 / 9:55 pm

      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.

  10. Lynda
    May 29, 2016 / 10:47 am

    Love the white shirt! Where is it from?

    • Jennifer
      May 29, 2016 / 12:15 pm

      It is from J Jill last year. It’s got a bit of strech that makes it comfy!

  11. May 29, 2016 / 9:42 am

    I wear deffinily flat shoes while running errands. And a jeans or a dress without zippers and leggings and a cardigan.

    • Jennifer
      May 29, 2016 / 12:15 pm

      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.

  12. Atonia Walpole
    May 29, 2016 / 9:01 am

    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.

    • Jennifer
      May 29, 2016 / 12:13 pm

      Thanks! Hats are just a fun accessory that polishes my look most days!

  13. Jeannette lipinski
    May 29, 2016 / 8:37 am

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

    • Jennifer
      May 29, 2016 / 12:12 pm

      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.

  14. May 29, 2016 / 8:03 am

    Great look, polished but comfortable! Like you, I’ve learned to keep a protein bar handy when I know I’ll be out for a few hours. Love that tote!!

    • Jennifer
      May 29, 2016 / 12:10 pm

      Thanks Susan! Polished is always a goal for me. And yes that tote is killer 🙂

  15. May 29, 2016 / 7:36 am

    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.

    • Jennifer
      May 29, 2016 / 12:09 pm

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

  16. Pam
    May 29, 2016 / 6:40 am

    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!

    • Jennifer
      May 29, 2016 / 12:07 pm

      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.

  17. Yvonne
    May 29, 2016 / 5:03 am

    Big white shirts have always been a staple in my closet too. You look great in that outfit.

    • Jennifer
      May 29, 2016 / 12:05 pm

      Thanks Yvonne, they are a huge favorite of mine too!!

    • Jennifer
      May 29, 2016 / 12:04 pm

      I agree Andrea! Have a great weekend too!

  18. May 29, 2016 / 4:16 am

    I just love all of your hats, Jennifer. The accessories make this such a chic look for running errands.

    • Jennifer
      May 29, 2016 / 12:03 pm

      I’ll get you in a hat yet!

  19. Rose
    May 29, 2016 / 3:50 am

    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.

    • Jennifer
      May 29, 2016 / 11:52 am

      This is a J Jill blouse from last year. I usually wear a tank under white shirts, but not under this one because the fabrics is cotton heavy enough not to. It’s on sale here:
      The French Kande does not go on sale as far as I know. These were investments to be sure, but I have never regretted buying them. They seem to modernize my whole look!

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