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?




  1. 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.

  2. 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?

  3. 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.

  4. 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.

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

  6. 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.

  7. 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.

  8. 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.

  9. 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.

  10. 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?

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

  11. 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!

  12. 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!

  13. 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.

  14. 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.

    1. 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.

    2. 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.

    3. 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!

  15. 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.

  16. 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.

  17. 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

    1. 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.

  18. 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!

  19. 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 😀

  20. 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.

  21. 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.

  22. 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!

  23. 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!!

    1. 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.

  24. 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.

  25. 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.

  26. 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.

  27. 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!

  28. 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 .

  29. 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.

  30. 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.

      1. 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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