I'm a Stylist—9 Incredibly Chic Flat-Shoe Outfits I Plan on Copying This January

Now, don’t get me wrong. There’s a time and a place for sky-high heels. Birthday parties, nights out with friends and those rare occasions you can go from door to Uber to door. But in my opinion, running around day to day is not one of them. Whether I’m commuting into the office or heading out for brunch at the weekend, I’m a comfort-first girl always. What can I say? Comfort means confidence in my eyes! But, my aversion to heels doesn’t mean my outfits have to feel any less elevated (no pun intended). 

There are some classic flat shoe combinations that reliably look chic, and to prove it, I’ve put together an edit of looks below from some of the most stylish women I know. Think of this as a handy reference point. A bit like that digitised wardrobe in Clueless. Bookmark it, or screenshot to your heart’s content. And then every time you need comfortable yet polished outfit inspiration in the mornings, you can check back. Perfect for January when none of us have any clue what to wear, right?

Keep scrolling, and you’ll find nine incredibly chic outfits to wear with flat shoes. Most consist of classic wardrobe pieces you probably already own, but I’ve also added links to shop them just in case you see anything your capsule might benefit from. From easy-to-re-create wide-leg trouser outfits to jeans-and-ballet-flat combos that actually work, your feet will thank you for these. Scroll on to discover the flat shoe outfits I'm living in in 2024.

1. Camel Coat + Wide Jeans + Loafers


(Image credit: @modestmira_)

Style Notes: This look has all the classic components of a fail-safe winter outfit. Longline coat? Check. Knitted turtleneck? Check. Killer shoes? Check.

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2. Quilted Jacket + Colourful Scarf + Black Flats


(Image credit: @thatgirlyusra)

Style Notes: It's freezing out, which means it's time for Acne's sell-out supersized scarf to shine. Pair yours with a quilted coat for maximum cosiness.

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3. Striped Shirt + Pleated Trousers + Birkenstocks


(Image credit: @chiarasatelier)

Style Notes: Birkenstock's shearling-lined slides have been heavily relied-upon so far this winter. I love how they look with plisse trousers and a relaxed shirt.

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4. Fluffy Knit + Maxi Skirt + Sneakers


(Image credit: @francescasaffari)

Style Notes: If you're someone who always feels dressed up in anything that isn't jeans, wear your maxi skirt with trainers and a slouchy knit for a laid-back feel.

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5. Neutral Jumper + Straight Jeans + Mary Janes


(Image credit: @tamaramory)

Style Notes: Jeans and a jumper is probably the easiest combination at this time of year, and it just so happens to look great with flat shoes, too.

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6. Vintage Trench Coat + Puddle Pants + Square-Toe Flats


(Image credit: @marina_torres)

Style Notes: This is exactly the kind of outfit I could wear day in, day out: fuss-free, comfortable and totally chic. Thanks for the inspiration, Marina.

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7. Shearling Jacket + Mini Skirt + Chunky Loafers


(Image credit: @emmanuellek_)

Style Notes: You can always count on a Parisian to make loafers look their best. Mini skirts and shearling coats are both super relevant right now, so I'll be recreating this ensemble ASAP.

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8. Blazer + Midi Dress + Derby Shoes


(Image credit: @frannfyne)

Style Notes: For an elevated everyday look, try styling a relaxed midi dress with black derby shoes and a fitted blazer. So chic, without compromising on comfort.

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9. Knitted Cardi+ Loose Jeans + Ballet Flats


(Image credit: @anoukyve)

Style Notes: I can't get enough of knitted co-ords (Reformation makes some great sets!) and adore how them with classic blue jeans and ballet flats.

Shop the look:

This story was published at an earlier time and has since been updated.

Next Up: 13 Elegant Pieces That Will Make Your Wardrobe a More Luxurious Place

Emily Dawes
Affiliate Editor

Emily Dawes is the very definition of a fashion multi hyphenate. An editor, stylist and writer with over eleven years’ worth of experience in the industry, Emily is known for her impeccable taste, elegant outfit choices and being able to spot the next big thing in fashion from a mile off. Our readers loyally trust her advice and shopping suggestions; so much so she began her own column documenting the most expensive-looking pieces on the high street, which has become a top-performing piece of content for the Who What Wear brand.

Emily has worked for Who What Wear UK since 2020 in a myriad as roles, spanning from contributing editor and branded content editor. Now, she holds the position of affiliate editor and is responsible for the brand’s overall affiliate strategy, ideation and content execution. Working closely with Who What Wear UK’s affiliate manager, Emily has been instrumental in securing and nourishing brand partnerships, surpassing her goals as standard. Leading the team in tentpole shopping moments including Black Friday and Peak Trading, with Emily’s guidance and leadership, team Who What Wear is in a stronger affiliate position than ever before.

Prior to joining the Who What Wear team, Emily served as YOU Magazine’s acting fashion editor where she managed the fashion team and oversaw all fashion content output for the fast-paced weekly title. Emily is a stylist in her own right, having worked with a slew of VIP clients including writer and television personality, Elizabeth Day, as well as styling and art directing several celebrity cover shoots for glossy print publication, Grazia. Her adept fashion knowledge means brands regularly sought out to work with her as a consultant: previously she has developed marketing and content plans for brands for Cocoon and Edge of Ember. Before entering the industry, Emily obtained a Bachelor of Arts in English and American Studies with International Study from Nottingham University. Fun fact: Emily spent a year studying in America which saw her join a sorority during her time there.

When she’s not working or tracking down the chicest, new-in items to share with our audience, you’ll find Emily bestowing her East London home with her stylish flair, reading everything from the classics to cowboy romance novels and escaping to the country with husband, baby boy and dog, Roo, whenever she can.

Emily is currently on maternity leave.