How to Look Chic in Flat Shoes

How to Look Chic in Flat Shoes

I’ve walked far too many miles in tight, ill-fitting, and high heeled shoes that weren’t always comfortable. When I was younger I would happily suffer for cute shoes but no more. My feet have rebelled and common sense has ruled but I still want to look chic in flats!mules help casual outfit look chic in flats

Many years in ballet toe shoes, tight shoes, high heels, and the resulting 2 bunionectomy’s on the same toe is enough for me to say, no more. That doesn’t mean I’ll be wearing frumpy gnome type shoes anytime soon because no matter how comfy those are, they don’t match my style.sanke print helps you look chic in flats

I adore the look of sexy high heels and the lift it gives my petite self. Sometimes I’ll try them on at the store but the second I stand up I remember how silly this option is for me. They hurt, a lot! I can wear a few low heeled shoes these days but to be honest, flats are the comfiest.

When shopping for shoes, clicking the “comfort” tab category is not as scary as it used to be. Many brands have stepped up their game (bad pun) and new ones have entered that offer great style and comfort in a flat shoe. Here are some tips to help you look chic in flats.

How to find comfy flats

  1. Look for a cushioned insole and rubber sole.
  2. a wide and deep enough toe box to give your toes plenty of room. Jammed hammertoes are no fun.
  3. An arch support system that keeps my feet from getting tired.
  4. Enough “shoe” to grasp your foot firmly. There’s nothing worse than feeling like the shoe will slip right off.here's how to look chic in flats and a column of gray

 7 Ways to look chic in flat shoes

  1.  avoid overly chunky shoes that are hard to balance when they’re flat
  2.  look for a unique shape and unusual detailing.
  3.  have your shoes be the pop of color for your outfit
  4.  a pointed toe flat adds length to your leg and helps balance anything else you’re wearing
  5.  sparkly or metallic shoes add fun to every look.
  6.  neutral colored shoes make your legs look longer because they draw no attention.
  7. athleisure has become mainstream many women are wearing trainers and athletic shoes with everything so try them with wider leg pants or a maxi skirt to help balance their bulk.

Buy the best you can afford and they will last you a long time. Your feet are worth the investment and will thank you for it.

Check out my Pinterest board for inspiration and to capture fresh ideas. Women are forever coming up with clever ways to style their outfits with flat shoes and I love to save them because I firmly believe that it’s chic to be comfortable!

If you liked this post I would love if you would pin this to your Pinterest board

Also- 5 Ways to Make Your Legs Look Longer in Flat Shoes

What are your favorite comfort brands?

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


  1. Nyla
    August 30, 2020 / 5:26 am

    I have one somewhat flat foot and not the other; i want shoes that are the same across the bottom– no separate heel for stability and i cushiony bottoms. I have gravitated to Naturalizer, Joseph Seibel, BZeez, Born, Clarks, Softt and New Balance. If i pick up a shoe and it is heavy i don’t even try it on. I like cheetah, snake, metallics as well as black, red, pink that go with my wardrobe. I want a little sass with comfort!

  2. Rose
    August 29, 2020 / 7:03 pm

    Thank goodness they have attractive, comfortable shoes out there now! I felt the need to wear heels while working in real estate. I too had two bunions removed. At age 70 I’m so glad those days are over!

  3. Susan Byers
    May 30, 2020 / 9:17 am

    Jennifer…I love the Cheetah flat with cheetah button down top look❤ my rule with flats is to wear them where you plan to not walk alot. I agree they hurt but a fun look for crop pants in summer.

  4. Laura Rutledge
    May 30, 2020 / 8:37 am

    LOL, I’ve just been on a comfort shoe search too! Chacos makes a flip flop with arch support that I wear as a staple, Teva has some dressier slides I like, and Taos makes a really beautiful walking sandal, and the classic look of the lighter Birkenstocks can’t be beat for comfort. I’ve also recently discovered budget friendly Easy Spirit for a casual slip on sneaker and adorable ballet flats, also Earth Origins does a low heel comfort version of the high vamp mesh cut out sandal in blush that is really cute! But my secret comfort around the house, garden and walk the dog shoes are Crocs! No, no, not the clog things, the ballet flats come in cute colors, neutrals, I have black, bone, pink loafer & leopard slingback, they mold to your feet after you wear them a bit, and wash n dry off. They are also great for a rainy day. Happy feet, happy me!

  5. Joanne Stacey
    May 30, 2020 / 6:21 am

    I wear a narrow. I highly recommend Trotteers brand of shoes. They have many nice flat shoes and they keep their shape and last.

  6. Kathy C.
    May 29, 2020 / 6:22 pm

    No one has mentioned shoes by Born, which make up 75% of the shoes in my closet. As a 1st grade teacher, I am on my feet all day, and I don’t feel like I have to kick them off the minute I get home. They last forever, too!

    • Jennifer
      May 29, 2020 / 6:43 pm

      My daughter loves Born. I need to check them

  7. Wanda
    May 29, 2020 / 6:09 pm

    After multiple stress fractures due to osteoporosis, I find that Hoka (athletic, pure comfort!), Vionic, and Alegria shoes are the brands that keep my feet happy most of the time. Also, Naot and Birkenstock are great contenders as well. When I shop for shoes, I look for a rigid sole – if I I can bend the sole of the shoe, I put it right down and move on. I know I must look odd trying to to bend and twist each shoe I’m considering for purchase. I love the recommendations from readers here- I will check them out!

    • Jennifer
      May 29, 2020 / 6:42 pm

      Ouch! Yes I’m loving all these suggestions too

  8. Brigid
    May 29, 2020 / 12:18 pm

    My feet were the first things to go!! They started going south in my fifties and are still headed that way at 73! I am very fond of Grasshoppers. They come in different widths and I require a wide. They are very reasonably priced and make a nice looking casual shoe. The insole is well padded but can be removed. Thanks for all the suggestions ladies. I now have some other brands to look for.

    • Jennifer
      May 29, 2020 / 5:15 pm

      My readers are the very best!!

  9. Sharon
    May 29, 2020 / 12:11 pm

    I’ve worn Naots for years and think it’s time to try some of these suggestions. Thank you!

  10. Kay
    May 29, 2020 / 12:09 pm

    Bernie Mev. They stretch.

  11. Catherine
    May 29, 2020 / 11:32 am

    Excellent advice, I can tell this is from someone who knows! I have prescription orthotic insoles which allows me a lot more choice but as a result I look for shoes that have removable insoles. Summer sandals can be a challenge for those I follow the advise you have given here. I have even found some that I can walk for miles in without pain. They were pricey but when calculate the cost per wear worth it. Who wants to seal up their feet during summer heat my toes like to be free(ish). Free in a supportive and soft environment! Aging is not for wimps! Thanks again for your honest and helpful posts.

    • Jennifer
      May 29, 2020 / 5:15 pm

      Comfortable shoes are worth what we need to pay to have them. I would rather have fewer pairs and know they are comfy.

  12. Joan
    May 29, 2020 / 11:30 am

    Any ideas for me? I have narrow feet as well as flat feet and a bunion on my right big toe which has slightly turned that toe up higher than the rest. And my second toes are almost 1/2 inch longer than my big toes. Buying closed-toe shoes are extremely tricky and closed heels tend to slip off my feet. Sandals have become my go-to choice, but they have to have a thong to anchor my feet inside. Without that toe stop, my feet just slide right off the front of the sandal. So flip flops are best for me. I buy the Clarks flip flops which are very common footwear here in Florida. Also certain styles of SAS sandals work for me. Any other brands/styles to consider?

    • Jennifer
      May 29, 2020 / 5:14 pm

      Check out sandals that cover the top of your foot and are anchored by the big toe. Paul Green comes to mind for those.

  13. Deborah
    May 29, 2020 / 11:29 am

    Hard to find comfortable shoes! Especially when you have narrow feet!!
    Clarks is about the only shoe I’ve found that is affordable AND makes Narrow widths. Even then, still need something more comfortable. Vionic is good, but doesn’t make narrow widths.

  14. Norma G
    May 29, 2020 / 11:23 am

    Shoes! Shoes! Shoes! Love me some cute shoes. BUT! Being diagnosed with plantar fasciitis about 12 years ago should changed my buying plans. The podiatrist I saw at the time suggested Clark’s and that was the day I purchased my first pair. I can’t wear “flat” flats, I need a very slight rise in the heel area. No more flip flops, no going barefoot, and everything must have good arch support. I wore a corrective boot to bed every night for over 2 years to help ease the pain of PF in my left foot. I have expanded my shoe wardrobe immensely over the years to over 25 pairs of Clarks, some Naturalizer, Sketcher, Amalfi, Avon Cushion Walk and a few random brands. Low wedges and some low heels are included, but mostly shoes that would be considered flats, but aren’t really flat. I can walk for miles without pain ( and I have) when the shoes are supportive, but they must be stylish too. Shoe obsession, YES, but not the sacrifice of comfort.

  15. Maggie Woodruff
    May 29, 2020 / 11:10 am

    Shoes I find incredibly comfortable are L’ Amour Des. I have 7 pairs…different colors and styles, some the same style, different colors!!

    • Jennifer
      May 29, 2020 / 5:12 pm

      I only have one of theirs but have two others in my virtual shopping cart:)

  16. Penelope
    May 29, 2020 / 10:31 am

    Agree that most flats are comfortable and a safer option as we get older and less agile! I look for shoes with non slippery soles. We get rain almost daily and plastic or slick leather soles are a hazard. I can’t wear those slip on casual shoes ( canvas or clogs) that have only a slight little lip for a back, or open toed flats, or high vamps. Low vamp, pointed toes are best for me and I do like the feminine look of sling backs.
    Shoes are always a challenge for me and I never can risk mail order. Frustrating in current situation.

    • Evelyn
      May 29, 2020 / 10:54 am

      I use mail order from Zappos.com. Easy return! No shipping either way!

  17. Roxanne
    May 29, 2020 / 10:02 am

    After shattering my heel into pieces falling off a ladder, I now have a foot full of hardware! My surgeon said look for shoes that do not bend at all in the sole. He was right, that is the only thing that allows me to walk without limping or pain. I love Dansko, Kork-Ease, some Clarks, and my go to for sandals is Romika for a day of shopping. And Hoka athletic shoes for the gym. The doctor told my husband I could only wear expensive shoes now! I would love to see some ideas on how to style dresses when wearing flats. Weddings and cocktail parties make me feel frumpy no matter how beautiful the dress.

    • Jennifer
      May 29, 2020 / 5:11 pm

      That sounds so painful. I will see what I can find for you.

  18. Sarah
    May 29, 2020 / 9:34 am

    Munro shoes are about the only shoes made in the USA. The are made in Hot Springs, Arkansas, and even have a factory outlet there. Some great buys.

    • Terry
      May 29, 2020 / 2:03 pm

      I’ll add SAS shoes made in San Antonio, TX.

  19. Carolyn
    May 29, 2020 / 8:50 am

    Flat shoes!! Knee problems!! Feet that hurt from years of high heels!!
    This is a great post. My podiatrist told me to wear sneakers with inserts. That’s ok at home, but sometimes I need a bit more. Everybody has given me a great list of shoes to check out. I like Munro.

  20. Molly
    May 29, 2020 / 8:11 am

    Shoes! I LOVE SHOES! But they don’t love me! Aargh! This post was right on Jennifer! ❤️ All of the tips and posts from other readers are so helpful! I do have a question about Rothy’s though. They have some of the cutest shoes I’ve ever seen, I even went to the store in San Francisco thinking it would be like Mecca!
    However you can fold the shoes like oragami! Isn’t one of the traits of a comfort shoe the fact that it is stable?

    • Penelope
      August 29, 2020 / 8:53 pm

      Yes, they are cute but have no stability or support. I used mine as at home Slippers for a while, then gave them away.

  21. Libda
    May 29, 2020 / 7:56 am

    I would love to find a flat shoe that doesn’t hurt my left foot! I won’t give up looking! The outfits you showed with those shoes are fantastic!

    Thank you for always inspiring me!

    By the way, this is my last official day as a Special Education Preschool Teacher! Yay!

    • Jennifer
      May 29, 2020 / 8:19 am

      Congratulations!! Onward to fresh adventures.

  22. Cyndi
    May 29, 2020 / 7:53 am

    Inner soles work well for me too. I switched out my heels for flats long ago, and although I’m short I’ve resigned my self and adjusted. Loving your all gray outfit with the hat – what a chic look!

  23. Eve
    May 29, 2020 / 7:04 am

    I am a believer in adding inter soles to flats. Before I write off a cute pair, I alway see if that would make a difference. The right inter sole can put a smile on your face.
    All these flats are so cute. i am leaning heavily on my loafers these days. I have a black pair that I grab when I’m in a hurry and absolutely need to be comfortable not think about my feet. Should you wear black stockings with black flats? I do because I don’t like that white foot look.

  24. Jane
    May 29, 2020 / 7:00 am

    I’ve recently had to start wearing orthotics due to hip pain. Can anyone recommend a shoe Brand that I can take the insoles out? I found a pair at Walmart of all places that look like Sketchers that the insoles come out.

    • Adrienne C Kushner
      May 29, 2020 / 8:03 am

      I have had issues with plantar faciitis, crossover toe. My hip and one knee is now starting to complain. Foot doctors and physical therapists have recommended Brooks sneakers, Dansko, and Klogs. In the long run, they cost less than shoes you find at Walmart. Dansko and Klogs make a wide variety of comfort shoes in many styles including sandals. They allowed me to enjoy a sight-seeing trip to London and Paris in comfort and style.

    • Ann M
      May 29, 2020 / 8:10 am

      Jane, Munro shoes have removable insoles and are high quality. They’re on the pricey side, but I’ve decided it’s worth it to pay for no barking dogs. Sometimes Nordstrom has them on sale; also Zappos.

      • Jennifer
        May 29, 2020 / 8:21 am

        I love my Munros too

    • Cindy
      May 29, 2020 / 8:23 am

      Actually many shoes have removable soles. Rothy’s being one of them. You sometimes need to size up a half or full size in order to fit your orthotic into them. Hope this helps!

  25. Audrey
    May 29, 2020 / 6:37 am

    Love your suggestions for chic flats. Would like to hear from you on flats with dresses. Thanks for all the ideas you share, look forward to them each time.

  26. Rose
    May 29, 2020 / 6:26 am

    I’m with you all the way here! I’m finding I don’t buy as many shoes as I used to. I go back to my comfortable ones every time. Since the stay at home order I’ve been wearing Nikes most days.

  27. Jan
    May 29, 2020 / 6:23 am

    Through trial and error, (ahh, let’s say “lots of error”) I have realized that a reasonable investment in a good shoe is worth it!
    I like a full toe box but it can be tricky to find without having my foot feel like it is slipping.
    I do like the Teva sandal and also have Sketchers, Earth and Vionic in my closet.
    I will research a lot of the great suggestions that were made today. This is an important subject for a lot of us. Gone are the days of suffering with sore feet for the sake of a fashionable look. Nothing stays the same for very long! Lol

    • BJ
      May 29, 2020 / 6:58 am

      I have found that Monroe, Fitflop, Naot and Beautifeel are now my go to brands. The latter is expensive but so comfortable and well made. I made it through my daughter’s wedding in a pair of Beautifeel kitten heels and lately I never wear anything but flats.

  28. Francesca B.
    May 29, 2020 / 6:14 am

    I like Kork Ease and Dansko for sandals and Keen for walking. And for summer especially Birkenstocks! Also a big fan for Rothy’s, for long hours standing and looking good they are the best. I do own classy high heels in navy and nude for special occasions but they don’t get much use now as I much prefer being lower to the ground.
    Great post thank you Jennifer!

  29. Jes
    May 29, 2020 / 6:10 am

    Love your style and I’m with you, no more uncomfortable shoes! There are many choices for cute shoes and I don’t have to ruin my feet 😀

  30. Kim Metcalf
    May 29, 2020 / 6:09 am

    I buy almost all my shoes from The Walking Company. Can find some of the same brands on Zappos also. Favorite brands are Taos, Ecco, Abeo and Dansko. I come from a long line of bad feet. Have already had bunion surgery and joints cleaned out. I also wear orthotics but with some of these brands I don’t have to because they are already built in.

    • Jennifer
      May 29, 2020 / 8:22 am

      You just reminded me of that day in high school when I drove my Mom home from her bunion surgery.

  31. Linda Henderson
    May 29, 2020 / 5:59 am

    I have always loved shopping for shoes. For summer I have been looking at purchasing some cute but comfortable sandals or flip flops. How about a post on those options if you are interested. Thanks.

  32. jmp
    May 29, 2020 / 5:49 am

    What a timely post for me! I have struggled to find cute and comfy flat shoes forever. Having taught school for many years, I spent days on my feet and high heels just killed me. Thanks for all of the suggestions. For cute boots and athletic shoes, my go to is Rieker and Remonte. Lots of colors and styles!

    • Jennifer
      May 29, 2020 / 7:15 am

      I think many of us are struggling with our feet;)

  33. - Vicki Mikola Dack
    May 29, 2020 / 5:22 am

    Sorry to say that any Pointy shoe cramps my toes. (Can remember my Sunday “Dress” shoes from the 1960’s; ouch!) perfer the semi-oval/round and square design. And once your arches start disappearing have to adjust no matter what with inserts! Shoes are my weakness — just ask my husband!!

    • Gail
      May 29, 2020 / 5:34 am

      If you have problems with bunions in any way, pointy shoes are your worst enemy….they push that big toe over – encouraging bunions to form even more.

    • Jennifer
      May 29, 2020 / 5:39 am

      My feet are wide so pointy toes aren’t usually the best for me either. My shoes collection is a bit out of control

  34. Michele
    May 29, 2020 / 5:15 am

    I have always been a fan of Naturalizer shoes and recently splurged on a pair of Ecco shoes during one of Nordstrom’s fantastic pandemic sales.

  35. Sue McLaughlin
    May 29, 2020 / 4:58 am

    My favourite brand for comfort here in the UK is Sole Bliss. They have very stylish shoes for women with bunions, hammer toes and wide feet. They ship overseas. Members of the Royal Family and Helen Mirren are customers. Check out their website.

    • Jennifer
      May 29, 2020 / 5:20 am

      I will! Thank you for the recommendation.

  36. Susan
    May 29, 2020 / 4:57 am

    Gucci loafers and Tods driving shoes were my ‘comfortable flats’, until I retired, the Australian dollar dropped, so I couldn’t justify their cost anymore. I had planned on a shoe shop for chic flats this month in Italy, but of course that trip was cancelled. I think I saw you model some Rothys which looked both comfortable and very smart, but they are not available in Australia – so the hunt is on for some new flats for which won’t necessitate me selling a kidney. Until then, I stick to my Rollies – an Australian label of very light, leather lace up shoes – in a variety of colours and funky patterns.

    • Jennifer
      May 29, 2020 / 5:16 am

      Rollie’s is a new brand to me. And yes, Rothys are very comfy.I love mine

  37. Lezlie Davis
    May 29, 2020 / 4:48 am

    Have you tried Rothy’s? My bestie wears them all of the time. I recently bought a pair of the points. I wasn’t sure (because they are pricey), but once I wore them for a day with a lot of walking, I realized my feet felt great at the end of the day. They are amazing! And their washable. I think they look very chic. My pair are a blue gingham type print. I’m definitely investing in more!

    • Jennifer
      May 29, 2020 / 5:13 am

      I do love Rothys too, I’ve almost worn my leopard pair out:)

  38. Betsy Forsland
    May 29, 2020 / 4:45 am

    I love both my Frye ballet flats , which have held up for several years of repeated wear , and my new R0thy’s, so comfortable and even washable .

  39. Pamela Over 50 Feeling 40
    May 29, 2020 / 4:38 am

    I love my Rockport and Clark flats for nicer shoes. ECCO is also in my closet. These brands are great for the feet and look good. I am now an all-flat wearing girl and I love that there are so many options.

    • Jennifer
      May 29, 2020 / 5:12 am

      Ecco is one of my favs too:)

  40. sheryl beil
    May 29, 2020 / 4:29 am

    currently looking for a favorite brand of flats…i use to like naturalizer, but the last two pair seemed tight across the top of the toes. i do like hush puppies chaste ballet. i bought a pair of Frye’s last year, but had to buy inserts to get a comfortable wear. the ones i reach for the most are my skechers, but i would like something in the closet a bit dressier.

    • Jennifer
      May 29, 2020 / 5:06 am

      I love my Skechers too

      • Bea
        May 29, 2020 / 6:04 am

        Sketchers Go shoes are the most comfortable I have ever worn! They make some cute ballet type flats, and their sandals are sweet too.

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