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
- Dr. Scholl’s Women’s Friendly Ballet Flat – Multiple Color/Pattern Options
- Aerosoles Women’s Silver Platter Flat – Multiple Color/Pattern Options
- Dr. Scholl’s Women’s Refreshment Flat – Available in Black Knit Mesh & Navy Knit Mesh
- Hush Puppies Women’s Chaste Ballet Flat – Multiple Color/Patterns Available
- BOBS from Skechers Women’s Plush Fashion Slip-On Flat – Multiple Color/Pattern Options
- Easy Spirit Women’s YUGHE Flat – Multiple Color Options
- Sanuk Women’s Yoga Ballet – Available in Rose Gold, Silver, and Gold
- Sanuk Womens Yoga Eden Sidewalk Surfers Footwear – Available in Mint Floral, Black Floral, and Natural
- Naturalizer Utopia N/S Round Toe Synthetic Flats
- J.Renee Women’s Abeni Flat – Multiple Color/Pattern Options Available
- Cutout Lace Up Flats – Wide Width
- G.H. Bass & Co. Women’s Helene Ballet Flat – Available in Black and Bronze
- JBU by Jambu Women’s Juniper Ballet Flat –
- Easy Spirit Women’s Madella Flat – Available in Copper, Silver, and Black
- Franco Sarto Women’s Cash Loafer – Multiple Color Options
- crocs Women’s Isabella W Flat Shoe – Multiple Color Options
- Keds Women’s Teacup Crochet Fashion Flat Shoe – Multiple Color Options
- G.H. Bass & Co. Women’s Neville Flat Laceup Espadrille – Available in Coral and Navy
Summer Flats $50+
- Clarks Women’s Doraville Nest Slip-On Loafer – Multiple Color Options
- Hush Puppies Women’s Lolly Chaste Ballet Flat – Multiple Color Options
- Easy Spirit Women’s Panga Flat – Available in Pink, Black, and Natural
- Nicole Women’s Georgina Ballet Flat – Available in Light Gold, Angelface, and Black
- Naturalizer Women’s Kyndell Ballet Flat – Multiple Color Options
- Jambu Women’s Blossom Encore Flat – Multiple Color Options
- Skechers Sport Women’s EZ Flex Sweetpea Slip-On Flat – Multiple Color Options
- Clarks Women’s Propose Band – Available in Red, Pewter, and Nude
- Ecco Footwear Womens Women’s Taisha Modern Flat Ballet Flat – Available in White, Blush, & Misty
- Easy Spirit Women’s YANDRA Fla – Multiple Color Options
- Johnston & Murphy Women’s Tami Laser Ballet Rose Gold Metallic Suede Flat
- Jambu Women’s Deep Sea Mary Jane Flat – Multiple Color Options
- Rockport Women’s Total Motion 20mm Lazer Cut Out Ballet Ballet Flat – Multiple Color Options
- 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
- Sanuk Yoga Slinged Up Prints Gladiator Sandal – Multiple Color/Pattern Options
- Sanuk Yoga Slingback Prints Flip Flop – Multiple Color/Pattern Options
- Naturalizer Women’s Wendy Huarache Sandal – Multiple Color Options
- Aerosoles Women’s Chlose Together Gladiator Sandal – Available in Red and Gold
- JSport by Jambu Women’s Grace Slide Sandal – Multiple ColorOptions
- Dr. Scholl’s Women’s Classic Platform Sandal – Multiple Color/Pattern Options
- Easy Spirit Women’s Maralyn Wedge Sandals
- NaturalSoul by Naturalizer Aaliyah Women Open Toe Synthetic Pink Wedge Sandal
- Easy Spirit e360 Kabrina Women W Open-Toe Patent Leather Slingback Heel
- Birkenstock Molina Women Narrow Slides Sandal
- Muk Luks Women’s Courtney Beaded Flat Sandal
- Fringe Grommet Gladiator Sandals – Wide Width
- Easy Spirit Hattie Women Open-Toe Leather Slingback Sandal
- G.H. Bass & Co. Women’s Margie Flat Sandal – Multiple Color Options
Sandals $50+
- Rockport Cobb Hill Women’s Gabby-CH Heeled Sandal – Available in Tan, Black, and Khaki
- Clarks Women’s Leisa Cacti Slide Sandal – Multiple ColorOptions
- Gentle Souls Women’s Break My Heart 3 Flat Sandal – Available in Gold, Natural/Cork, and Navy
- Ecco Footwear Womens Touch 25 Hooded Dress Sandal
- Easy Spirit Women’s Julieta Dress Sandal – Available in Black and Light Gold
- Tall Knee Gladiator Sandals – Wide Width & Wide Calf
- Cushe Women’s Aurora Dress Sandal – Available in Rose and Tan
- FitFlop Women’s Biker Chic Slide Dress Sandal – Multiple Color Options
- 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
- Clarks Women’s Evianna Doyle Fisherman Sandal – Available in Black, Tan, and Cherry
- Naturalizer Women’s Lonnie Oxford
- Easy Spirit Women’s Gianetta Flat – Available in Pewter, Grey, and Black
- Sanuk Women’s Yoga Glitz Sidewalk Surfers – Available in Mint Snake, Silver Snake, and Natural Snake
- Sanuk Women’s Fiona Slip-On Shoe –Multiple Color Options
- Easy Spirit Women’s Gabi Ballet Flat – Available in Taupe and Black
- Daniel Green Women’s Joella Ballet Flat – Available in Blue and Multi
- Hush Puppies Bridie Avila W Round Toe Canvas Flats
- Old Friend Women’s Emily – Multiple Color Options
- Bass Women’s Gilmore Flat – Available in Brown and Black
- Soft Style by Hush Puppies Women’s Hula Flat– Multiple Color Options
- Dr. Scholl’s Women’s Joliet Ballet Flat – Multiple Color Options
- Aerosoles Women’s Richmond Flat – Multiple Color Options
- KEEN Women’s Cortona Ballet Shoe – Multiple Color Options
- Hush Puppies Women’s Ceil MT Slip-On Loafer – Multiple Color Options
- Sanuk Women’s Shorty TX Chill Flat – Available in Charcoal and Multi
- Clarks Women’s Evianna Fig Slip on Shoes –
- Clarks Women’s Faraway Field Oxford – Multiple Color Options
- Naturalizer Women’s Davonville Loafers Shoes = Multiple Color Options
- Hush Puppies Women’s ADENA PIPER Slip-On Loafer – Multiple Color Options
Fall Flats $50+
- Minnetonka Women’s Kilty Suede Moccasin – Multiple Color Options
- Aerosoles Women’s Super Soft Slip-On Loafer – Multiple Color Options
- FitFlop Women’s F-Pop Ballerina Suede Ballet Flat – Multiple Color Options
- Easy Spirit Women’s Karcie Ballet Flat – Availavle in Blue and Black
- Footprints by Birkenstock Tirano Leather Shoe – Available in Black and Pinecone/Mustard
- KEEN Women’s Cortona Bow CVS Shoe – Multiple Color/Pattern Options
- Soft Style by Hush Puppies Women’s Rory Flat – Multiple Color Options
- Dansko Women’s Lori Mary Jane Flat – Available in Black Nappa and Brown Nubuck
- Softwalk Women’s Naperville Ballet Flat – Multiple Color Options
- Skechers Women’s Rome Slip-On Loafer – Multiple Color Options
- Sanuk Women’s W Elle V. Eight Flat – Available in Black, Tobacco, and Burgandy
- crocs Women’s Lina Embellished Suede Ballet Flat – Available in Espresso, Navy, and Hazelnut
- Gentle Souls Women’s Erica Flat – Available in Oxblood, Taupe, and Black
- Camper Women’s TWS Mary Jane Flat – Multiple Color/Style Options
- 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
- Easy Spirit Women’s Kinseta Boot – Available in Black and Dark Brown
- Easy Spirit Women’s Dominaw Riding Boot – Available in Black, Dark Brown, and Black Multi
- Easy Spirit Women’s Nerola Mid Calf Thick Heel Boots
- Sanuk Women’s Honey Bee Fringe Bootie
- NaturalSoul by Naturalizer Sacred Round Toe Synthetic Knee High Boot
- Easy Spirit Women’s Patara Boot – Multiple Color Options
- Easy Spirit Almrose Women Round Toe Leather Black Bootie
- A2 by Aerosoles Women’s Ride with Me Riding Boot – Available in Black, Grey, and Dark Brown
- Woolrich Women’s Pocono Creek Winter Boot – Available in Java and Chinchilla
Cold-Weather Boots $50+
- Dr. Martens Women’s 1460 Re-Invented Victorian Print Lace Up Boot – Multiple Color/Pattern Options
- FitFlop Women’s Tall Mukluk Moc 2 Boot – Available in Chocolate Brown and All Black
- crocs Women’s Leigh Suede Wedge Shootie Boot – Available in Black, Tan, and Grey
- Clarks Women’s Carleta Lyon Boot
- Rockport Women’s Alanda Brogue Boots
- Dr. Scholl’s Women’s Breeanna Boot – Available in Taupe & Black Microfiber
- Hush Puppies Women’s Cyra Catelyn Boot – Multiple Color Options
- TOMS Womens Desert Wedges Boot – Multiple Color/Pattern Options
- Dr. Scholl’s Women’s Heathrow Boot – Wide Calf Available
- Dansko Women’s Buffy Ankle Boot
- A2 by Aerosoles Women’s Gold Role Bootie – Available in Blue, Black, and Brown
- Naturalizer Women’s Trebble Wide Shaft – Available in Black & Bark
- Aerosoles Women’s Plumming Bird Ankle Boot – Multiple Color Options
- Footprints by Birkenstock Loreto Leather Boots
- Naturalizer Women’s Ember Boot
- FitFlop Women’s Dash Boot
- Sanuk Womens Siena Boot Sidewalk Surfers Footwear – Available in Natural and Black/Brown
- 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
- Skechers Cali Women’s Vanguard Wedge Sandal – Available in Black and Natural
- Easy Spirit Senza Heels
- TOETOS SOLSOFT Open Toes Mid Heels Platform Wedges Summer Sandals – Mutliple Color Options
- Clarks Women’s Helio Float Wedge Sandal – Multiple Color Options
- A2 by Aerosoles Women’s Boyzenberry Wedge Sandal – Multiple Color Options
- Aerosoles Women’s A2 By Aerosoles Rotmail Sandals – Multiple Color Options
- Aerosoles Women’s Plum Tree Wedge Sandal – Multiple Color/Pattern Options
- Naturalizer Women’s Bashful Espadrille – Available in Bright Coral, Brown Gold, & Black
- Easy Spirit Laralee Open Toe Leather Wedge Sandal
- Geox Women’s Victory 3 Watercolor Wedge Sandal = Multiple Color Options
- T-Strap Mini Wedges – Wide Width
- J.Renee Women’s Jaynnie D’Orsay Pump
Summer Heels $50+
- Skechers Cali Women’s Rumblers-Beautiful People Wedge Sandal
- Hush Puppies Women’s Mora Malia Slide Sandal – Multiple Options Available
- Aerosoles Women’s Yet Another Gladiator Sandal – Multiple Color Options
- Clarks Women’s Pastina Lima Ankle Strap Sandal – Multiple Colors Available
- crocs Women’s Leigh Wedge Sandal – Multiple Color Option
- Rockport Cobb Hill Women’s Hannah-CH Wedge Sandal
- Soft Style by Hush Puppies Women’s Analee Dress Pump – Multiple Color/Pattern Options
- Rockport Women’s Sasha Brogue Oxford Shootie
- Soft Style by Hush Puppies Women’s Analee Dress Pump – Multiple Colors/Patterns Available
- Lace Up Wedges – Wide Width
- J.Renee Women’s Bailee Dress Pump – Multiple Color Options
- J.Renee Women’s Genie Dress Pump – Multiple Color Options
- Soft Style by Hush Puppies Women’s Aubrey Dress Pump – Mulitiple Color Options
- J.Renee Women’s Ditte Dress Pump – Multiple Color/Pattern Options
- J.Renee Women’s Enchanted D’Orsay Pump – Available in Black and Taupe
- J.Renee Women’s Pearlie Slide Pump – Available in Black, Savannah Gold, and Multi
- 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
- Easy Spirit Women’s Cleon Boot – Available in Navy Plaid, Black, and Dark Taupe
- Easy Spirit Women’s Raphael Rubber Dress Pump
- Easy Spirit Women’s Nareen – Available in Black and Gray
- Aerosoles Women’s Role Through Dress Pump – Multiple Color Options
- Aerosoles Women’s Dolled Up dress Pump – Multiple Color Options
- Aerosoles Women’s Starring Role Boot
- Earthies Women’s Prantini – Available in Black, Dark Taupe, and Blackberry
- Aerosoles Women’s Doodle Boots
- Aerosoles Strole Around Women Round Toe Suede Gray Heels – Available in Black and Grey
- Easy Spirit Women’s Rickeeta Dress Pump – Available in Black and Bronze
- Dr. Scholl’s Women’s Brilliant Pump – Available in Navy Dot and Navy Stripe
- Clarks Women’s Leather Brielle Chanel Wedge Pump – Multiple Color Options
- Earthies Mezzi Pumps – Available in Black and Chestnut
- Aerosoles Women’s Arivederci Dress Pump – Available in Black, Dark Blue, and Dark Wine
- Easy Spirit Women’s Liara Dress Pump
Cold-Weather Heels $50+
- Clarks Women’s Kendra Mix
- Clarks Women’s Rosalyn Nicole Slip-On Loafer – Multiple Color Options
- Dr. Scholl’s Women’s Alison Oxford – Available in Black & Brown
- Ecco Footwear Womens Women’s Sculptured 45 Plain Pump Dress Pump
- Hush Puppies Women’s Devynn Sisany Dress Pump – Available in Black and Tan
- Easy Spirit Women’s Coria Penny Loafer
- Rockport Women’s Gore Shootie Boot – Available in Windosor Wine, Black Leather, and Black Suede
- Aerosoles Women’s Jalapeno Ankle Boot
- Naturalizer Women’s Kaitlyn Pump
- Pink Wedge Sneakers – Wide Width
- Naturalizer Madelen Mary Jane Shoes
- Naturalizer Women’s Sharon Dress Pump –
- Naturalizer Fathom Women’s Heels Oxford Brown Size 8.5 M
- nicole Women’s Balzac Pump – Available in Black and Old Gold
- TSUBO Women’s Tattiana Dress Pump
- Clarks Women’s Bassett Mine Wedge Pump – Available in Grey Suede, Black Suede, and Black Leather
- J.Renee Women’s Veeva Rubber Dress Pump – Multiple Color Options