The Ultimate List of Fashionable and Comfortable Shoes

When I first started my part-time job working in retail I was told that the dress code was basically “be stylish, accessorize with statement pieces, and no-flip flops or tennis shoes.” Being stylish and accessorizing was pretty easy since everything I wear is basically from the store where I am working, but the hardest part for me to figure out was finding fashionable and comfortable shoes. I looked at my new manager and I asked “What on earth do you recommend for fashionable and comfortable shoes ? It seems like an oxymoron… Fashion AND comfortable enough that they wont kill my feet standing on this cold hard floor? Does that even exist?” She looked at me and said “I’m sorry, after 7 years in this business I still don’t have the answer for that…” So of course, I turned to the internet and tried some trial and error. After a few months of now working on my feet and somehow pulling off the fashion of it, I figured I’d share my findings for fashionable and comfortable shoes in all price ranges… You shouldn’t have to be completely miserable for style… My friend always has issues with her feet and shoes and if you’re the same, click here to see some shoes which may be suitable for you.

Fashionable and Comfortable Shoes

For years now I’ve been working a desk job where I have no dress code, nor does it really matter what I wear on my feet since I’m sitting all day. My friend recommended that I buy some Vessi waterproof sneakers but there are so many different shapes and styles of shoes that I want to buy! I can wear sneakers, flats, flip-flops, heels, boots, whatever-you name it. I never thought much of it, other than investing in some good shoes with arch support when the doctor said I had plantar fasciitis. Man, I was not happy when he said I wouldn’t be able to wear my large collection of flats and flip flops anymore, especially knowing that there were women’s flip flops for sale from Ann’s Cottage-so I dropped a few bills on some nice tennis shoes and some different colored Maui Flip Flops from Okabashi (seriously the cheapest and most supportive shoe I’ve found so far) and called it good. Luckily, after a few months of wearing them I was able to occasionally start wearing my normal shoes again. My new manager recommended I invest in boots whenever I could, and if I wanted to try and get away with something more basic I would need to add something to them to make them look more stylish. She said she wore Sanuk Slingbacks and then tied a black strip of fabric to it that she could wrap up her legs to make it look more stylish.

Fashionable and Comfortable Shoes for Summer

When I was told that I couldn’t wear flip flops or sneakers, I had to basically start from scratch with my shoe choices. It being Summer, I immediately set out to find some Summer shoe options-for me that meant sandals but there are a ton of other options out there for you.

Fashionable and Comfortable Summer Flats

No doubt about it, but your best bet when looking for comfortable shoes that are neither flip-flop nor running shoes, is a flat. However, even looking for a flat you’re going to want one that has significant padding, perhaps a little support, or are roomy enough you can put an insert in them. During the Summer, you’ll want flats that don’t cause your feet to sweat and aren’t too clunky so that you can pair them well with shorts, dresses, and other fun Summery outfits. Here are some of my favorites I’ve found that do their best to combine these qualities.

Summer Flats Under $50

1. Dr. Scholl’s Women’s Friendly Ballet Flat – Multiple Color/Pattern Options
2. Aerosoles Women’s Silver Platter Flat – Multiple Color/Pattern Options
3. Dr. Scholl’s Women’s Refreshment Flat – Available in Black Knit Mesh & Navy Knit Mesh
4. Hush Puppies Women’s Chaste Ballet Flat – Multiple Color/Patterns Available
5. BOBS from Skechers Women’s Plush Fashion Slip-On Flat – Multiple Color/Pattern Options
6. Easy Spirit Women’s YUGHE Flat – Multiple Color Options
7. Sanuk Women’s Yoga Ballet – Available in Rose Gold, Silver, and Gold
8. Sanuk Womens Yoga Eden Sidewalk Surfers Footwear – Available in Mint Floral, Black Floral, and Natural
9. Naturalizer Utopia N/S Round Toe Synthetic Flats
10. J.Renee Women’s Abeni Flat – Multiple Color/Pattern Options Available
11. Cutout Lace Up Flats – Wide Width
12. G.H. Bass & Co. Women’s Helene Ballet Flat – Available in Black and Bronze
13. JBU by Jambu Women’s Juniper Ballet Flat –
14. Easy Spirit Women’s Madella Flat – Available in Copper, Silver, and Black
15. Franco Sarto Women’s Cash Loafer – Multiple Color Options
16. crocs Women’s Isabella W Flat Shoe – Multiple Color Options
17. Keds Women’s Teacup Crochet Fashion Flat Shoe – Multiple Color Options
18. G.H. Bass & Co. Women’s Neville Flat Laceup Espadrille – Available in Coral and Navy

Summer Flats $50+

19. Clarks Women’s Doraville Nest Slip-On Loafer – Multiple Color Options
20. Hush Puppies Women’s Lolly Chaste Ballet Flat – Multiple Color Options
21. Easy Spirit Women’s Panga Flat – Available in Pink, Black, and Natural
22. Nicole Women’s Georgina Ballet Flat – Available in Light Gold, Angelface, and Black
23. Naturalizer Women’s Kyndell Ballet Flat – Multiple Color Options
24. Jambu Women’s Blossom Encore Flat – Multiple Color Options
25. Skechers Sport Women’s EZ Flex Sweetpea Slip-On Flat – Multiple Color Options
26. Clarks Women’s Propose Band – Available in Red, Pewter, and Nude
27. Ecco Footwear Womens Women’s Taisha Modern Flat Ballet Flat – Available in White, Blush, & Misty
28. Easy Spirit Women’s YANDRA Fla – Multiple Color Options
29. Johnston & Murphy Women’s Tami Laser Ballet Rose Gold Metallic Suede Flat
30. Jambu Women’s Deep Sea Mary Jane Flat – Multiple Color Options
31. Rockport Women’s Total Motion 20mm Lazer Cut Out Ballet Ballet Flat – Multiple Color Options
32. Taos Women’s Step It Up Mary Jane Flat – Multiple Color Options

Fashionable and Comfortable Sandals for Summer

The other best option in the Summertime is sandals. There are a surprising amount of sandals out there that fit in the “comfortable shoes” category, and even more than have a good structure for arch support even. I’m a flip-flop gal who doesn’t even own regular sandals, so I really had to do some looking and I’m still looking to order a few pair. Here are some of what I found…

Sandals Under $50

1. Sanuk Yoga Slinged Up Prints Gladiator Sandal – Multiple Color/Pattern Options
2. Sanuk Yoga Slingback Prints Flip Flop – Multiple Color/Pattern Options
3. Naturalizer Women’s Wendy Huarache Sandal – Multiple Color Options
4. Aerosoles Women’s Chlose Together Gladiator Sandal – Available in Red and Gold
5. JSport by Jambu Women’s Grace Slide Sandal – Multiple ColorOptions
6. Dr. Scholl’s Women’s Classic Platform Sandal – Multiple Color/Pattern Options
7. Easy Spirit Women’s Maralyn Wedge Sandals
8. NaturalSoul by Naturalizer Aaliyah Women Open Toe Synthetic Pink Wedge Sandal
9. Easy Spirit e360 Kabrina Women W Open-Toe Patent Leather Slingback Heel
10. Birkenstock Molina Women Narrow Slides Sandal
11. Muk Luks Women’s Courtney Beaded Flat Sandal
12. Fringe Grommet Gladiator Sandals – Wide Width
13. Easy Spirit Hattie Women Open-Toe Leather Slingback Sandal
14. G.H. Bass & Co. Women’s Margie Flat Sandal – Multiple Color Options

Sandals $50+

15. Rockport Cobb Hill Women’s Gabby-CH Heeled Sandal – Available in Tan, Black, and Khaki
16. Clarks Women’s Leisa Cacti Slide Sandal – Multiple ColorOptions
17. Gentle Souls Women’s Break My Heart 3 Flat Sandal – Available in Gold, Natural/Cork, and Navy
18. Ecco Footwear Womens Touch 25 Hooded Dress Sandal
19. Easy Spirit Women’s Julieta Dress Sandal – Available in Black and Light Gold
20. Tall Knee Gladiator Sandals – Wide Width & Wide Calf
21. Cushe Women’s Aurora Dress Sandal – Available in Rose and Tan
22. FitFlop Women’s Biker Chic Slide Dress Sandal – Multiple Color Options
23. Birkenstock Women’s Mayari Leather Thong Sandal – Available in Black, Habana, and Gold Brown

Fashionable and Comfortable Shoes for Cooler Weather

Now, of course we’re transitioning into Fall and Winter wear and I’m going to have to put away my fun Sanuks as soon as the weather chills… What will I turn to? Boots probably… I’ll keep wearing my flats and moccasins of course.

Fashionable and Comfortable Fall Flats

Personally, I think flats are probably the most well-rounded option for your comfortable shoes collection and wardrobe. Most can be worn through all weather (except maybe knee-deep snow) and most can be paired with either a dressier outfit or a casual outfit. Lots of great options, but here are some that seem more like “Fall” in color and/or style, and which maybe provide a little more coverage for your feet than the Summer Flats I’ve provided before.

Fall Flats Under $50

1. Clarks Women’s Evianna Doyle Fisherman Sandal – Available in Black, Tan, and Cherry
2. Naturalizer Women’s Lonnie Oxford
3. Easy Spirit Women’s Gianetta Flat – Available in Pewter, Grey, and Black
4. Sanuk Women’s Yoga Glitz Sidewalk Surfers – Available in Mint Snake, Silver Snake, and Natural Snake
5. Sanuk Women’s Fiona Slip-On Shoe –Multiple Color Options
6. Easy Spirit Women’s Gabi Ballet Flat – Available in Taupe and Black
7. Daniel Green Women’s Joella Ballet Flat – Available in Blue and Multi
8. Hush Puppies Bridie Avila W Round Toe Canvas Flats
9. Old Friend Women’s Emily – Multiple Color Options
10. Bass Women’s Gilmore Flat – Available in Brown and Black
11. Soft Style by Hush Puppies Women’s Hula Flat– Multiple Color Options
12. Dr. Scholl’s Women’s Joliet Ballet Flat – Multiple Color Options
13. Aerosoles Women’s Richmond Flat – Multiple Color Options
14. KEEN Women’s Cortona Ballet Shoe – Multiple Color Options
15. Hush Puppies Women’s Ceil MT Slip-On Loafer – Multiple Color Options
16. Sanuk Women’s Shorty TX Chill Flat – Available in Charcoal and Multi
17. Clarks Women’s Evianna Fig Slip on Shoes –
18. Clarks Women’s Faraway Field Oxford – Multiple Color Options
19. Naturalizer Women’s Davonville Loafers Shoes = Multiple Color Options
20. Hush Puppies Women’s ADENA PIPER Slip-On Loafer – Multiple Color Options

Fall Flats $50+

21. Minnetonka Women’s Kilty Suede Moccasin – Multiple Color Options
22. Aerosoles Women’s Super Soft Slip-On Loafer – Multiple Color Options
23. FitFlop Women’s F-Pop Ballerina Suede Ballet Flat – Multiple Color Options
24. Easy Spirit Women’s Karcie Ballet Flat – Availavle in Blue and Black
25. Footprints by Birkenstock Tirano Leather Shoe – Available in Black and Pinecone/Mustard
26. KEEN Women’s Cortona Bow CVS Shoe – Multiple Color/Pattern Options
27. Soft Style by Hush Puppies Women’s Rory Flat – Multiple Color Options
28. Dansko Women’s Lori Mary Jane Flat – Available in Black Nappa and Brown Nubuck
29. Softwalk Women’s Naperville Ballet Flat – Multiple Color Options
30. Skechers Women’s Rome Slip-On Loafer – Multiple Color Options
31. Sanuk Women’s W Elle V. Eight Flat – Available in Black, Tobacco, and Burgandy
32. crocs Women’s Lina Embellished Suede Ballet Flat – Available in Espresso, Navy, and Hazelnut
33. Gentle Souls Women’s Erica Flat – Available in Oxblood, Taupe, and Black
34. Camper Women’s TWS Mary Jane Flat – Multiple Color/Style Options
35. Taos Women’s Jiminy Oxford – Multiple Color Options

Fashionable and Comfortable Boots

The other best bet for cooler-weather is boots! Just like my manager said, invest in boots! They go great under dresses, over leggings/skinny jeans, or with most all-around outfits. Plus, if they aren’t already supportive they typically have plenty of room to stuff an insert into so you can make them supportive.

Cold-Weather Boots Under $50

1. Easy Spirit Women’s Kinseta Boot – Available in Black and Dark Brown
2. Easy Spirit Women’s Dominaw Riding Boot – Available in Black, Dark Brown, and Black Multi
3. Easy Spirit Women’s Nerola Mid Calf Thick Heel Boots
4. Sanuk Women’s Honey Bee Fringe Bootie
5. NaturalSoul by Naturalizer Sacred Round Toe Synthetic Knee High Boot
6. Easy Spirit Women’s Patara Boot – Multiple Color Options
7. Easy Spirit Almrose Women Round Toe Leather Black Bootie
8. A2 by Aerosoles Women’s Ride with Me Riding Boot – Available in Black, Grey, and Dark Brown
9. Woolrich Women’s Pocono Creek Winter Boot – Available in Java and Chinchilla

Cold-Weather Boots $50+

10. Dr. Martens Women’s 1460 Re-Invented Victorian Print Lace Up Boot – Multiple Color/Pattern Options
11. FitFlop Women’s Tall Mukluk Moc 2 Boot – Available in Chocolate Brown and All Black
12. crocs Women’s Leigh Suede Wedge Shootie Boot – Available in Black, Tan, and Grey
13. Clarks Women’s Carleta Lyon Boot
14. Rockport Women’s Alanda Brogue Boots
15. Dr. Scholl’s Women’s Breeanna Boot – Available in Taupe & Black Microfiber
16. Hush Puppies Women’s Cyra Catelyn Boot – Multiple Color Options
17. TOMS Womens Desert Wedges Boot – Multiple Color/Pattern Options
18. Dr. Scholl’s Women’s Heathrow Boot – Wide Calf Available
19. Dansko Women’s Buffy Ankle Boot
20. A2 by Aerosoles Women’s Gold Role Bootie – Available in Blue, Black, and Brown
21. Naturalizer Women’s Trebble Wide Shaft – Available in Black & Bark
22. Aerosoles Women’s Plumming Bird Ankle Boot – Multiple Color Options
23. Footprints by Birkenstock Loreto Leather Boots
24. Naturalizer Women’s Ember Boot
25. FitFlop Women’s Dash Boot
26. Sanuk Womens Siena Boot Sidewalk Surfers Footwear – Available in Natural and Black/Brown
27. Dansko Women’s Ames Boot– Multiple Color Options

Fashionable and Comfortable Heels

Okay, so I would definitely never recommend a pair of heels if you are working a retail (or any other job where you have to stand on your feet) shift, but sometimes you have to put on a pair of heels for a work function, date, or even a very short shift on a high-fashion holiday/sale day. In that case, you’ll want to make sure you have a great pair of heels that look good and feel good, so you aren’t feeling too broken after a couple of hours dancing, walking, or standing in them. Here are some of the best ones I could find that fit that category for both the warm and cold months…

Fashionable and Comfortable Heels for Summer

Summer is going to require a lot more options for open toe, air flow, and showy shoes. Here are some lovely options that look great and feel great-or at least better than some of the alternatives…

Summer Heels Under $50

1. Skechers Cali Women’s Vanguard Wedge Sandal – Available in Black and Natural
2. Easy Spirit Senza Heels
3. TOETOS SOLSOFT Open Toes Mid Heels Platform Wedges Summer Sandals – Mutliple Color Options
4. Clarks Women’s Helio Float Wedge Sandal – Multiple Color Options
5. A2 by Aerosoles Women’s Boyzenberry Wedge Sandal – Multiple Color Options
6. Aerosoles Women’s A2 By Aerosoles Rotmail Sandals – Multiple Color Options
7. Aerosoles Women’s Plum Tree Wedge Sandal – Multiple Color/Pattern Options
8. Naturalizer Women’s Bashful Espadrille – Available in Bright Coral, Brown Gold, & Black
9. Easy Spirit Laralee Open Toe Leather Wedge Sandal
10. Geox Women’s Victory 3 Watercolor Wedge Sandal = Multiple Color Options
11. T-Strap Mini Wedges – Wide Width
12. J.Renee Women’s Jaynnie D’Orsay Pump

Summer Heels $50+

13. Skechers Cali Women’s Rumblers-Beautiful People Wedge Sandal
14. Hush Puppies Women’s Mora Malia Slide Sandal – Multiple Options Available
15. Aerosoles Women’s Yet Another Gladiator Sandal – Multiple Color Options
16. Clarks Women’s Pastina Lima Ankle Strap Sandal – Multiple Colors Available
17. crocs Women’s Leigh Wedge Sandal – Multiple Color Option
18. Rockport Cobb Hill Women’s Hannah-CH Wedge Sandal
19. Soft Style by Hush Puppies Women’s Analee Dress Pump – Multiple Color/Pattern Options
20. Rockport Women’s Sasha Brogue Oxford Shootie
21. Soft Style by Hush Puppies Women’s Analee Dress Pump – Multiple Colors/Patterns Available
22. Lace Up Wedges – Wide Width
23. J.Renee Women’s Bailee Dress Pump – Multiple Color Options
24. J.Renee Women’s Genie Dress Pump – Multiple Color Options
25. Soft Style by Hush Puppies Women’s Aubrey Dress Pump – Mulitiple Color Options
26. J.Renee Women’s Ditte Dress Pump – Multiple Color/Pattern Options
27. J.Renee Women’s Enchanted D’Orsay Pump – Available in Black and Taupe
28. J.Renee Women’s Pearlie Slide Pump – Available in Black, Savannah Gold, and Multi
29. J.Renee Women’s Jaynnie D’orsay Pump – Available in Blue/White, Black/White, and Yellow/White

Fashionable and Comfortable Cold-Weather Heels

In the winter you’re going to want heels that provide a bit more coverage for your feet and that keep your toes warm. Here are some great options!

Cold-Weather Heels Under $50

1. Easy Spirit Women’s Cleon Boot – Available in Navy Plaid, Black, and Dark Taupe
2. Easy Spirit Women’s Raphael Rubber Dress Pump
3. Easy Spirit Women’s Nareen – Available in Black and Gray
4. Aerosoles Women’s Role Through Dress Pump – Multiple Color Options
5. Aerosoles Women’s Dolled Up dress Pump – Multiple Color Options
6. Aerosoles Women’s Starring Role Boot
7. Earthies Women’s Prantini – Available in Black, Dark Taupe, and Blackberry
8. Aerosoles Women’s Doodle Boots
9. Aerosoles Strole Around Women Round Toe Suede Gray Heels – Available in Black and Grey
10. Easy Spirit Women’s Rickeeta Dress Pump – Available in Black and Bronze
11. Dr. Scholl’s Women’s Brilliant Pump – Available in Navy Dot and Navy Stripe
12. Clarks Women’s Leather Brielle Chanel Wedge Pump – Multiple Color Options
13. Earthies Mezzi Pumps – Available in Black and Chestnut
14. Aerosoles Women’s Arivederci Dress Pump – Available in Black, Dark Blue, and Dark Wine
15. Easy Spirit Women’s Liara Dress Pump

Cold-Weather Heels $50+

16. Clarks Women’s Kendra Mix
17. Clarks Women’s Rosalyn Nicole Slip-On Loafer – Multiple Color Options
18. Dr. Scholl’s Women’s Alison Oxford – Available in Black & Brown
19. Ecco Footwear Womens Women’s Sculptured 45 Plain Pump Dress Pump
20. Hush Puppies Women’s Devynn Sisany Dress Pump – Available in Black and Tan
21. Easy Spirit Women’s Coria Penny Loafer
22. Rockport Women’s Gore Shootie Boot – Available in Windosor Wine, Black Leather, and Black Suede
23. Aerosoles Women’s Jalapeno Ankle Boot
24. Naturalizer Women’s Kaitlyn Pump
25. Pink Wedge Sneakers – Wide Width
26. Naturalizer Madelen Mary Jane Shoes
27. Naturalizer Women’s Sharon Dress Pump –
28. Naturalizer Fathom Women’s Heels Oxford Brown Size 8.5 M
29. nicole Women’s Balzac Pump – Available in Black and Old Gold
30. TSUBO Women’s Tattiana Dress Pump
31. Clarks Women’s Bassett Mine Wedge Pump – Available in Grey Suede, Black Suede, and Black Leather
32. J.Renee Women’s Veeva Rubber Dress Pump – Multiple Color Options