The 5 Pairs of Flats I Reach for the Most

Whenever I share work outfits, one of the pieces of feedback I get the most is that some of you can’t or just don’t like wearing heels. I have to admit, over the past two years with WFH and having two little ones, most of my heels collection has been sitting untouched inside our Ikea billy bookcases. A while back I posted these outfits with flat shoes and wanted to share more ways I’ve been re-wearing these same flats and staple pieces. I also shared these looks in an IG Reel. If I look at the categories of flats I tend to reach for the most for both comfort and versatility, these would be the top 5!

1. Stretchy Knit Flats

business casual fall outfits with flats

Rothy’s flats sz 5.5 (JWANG20 for $20 off $100+), Gap sweater xsP, J.Crew pants 00P, Naghedi bag

Rothy’s are some of my go-to shoes for travel or walking due to the stretch and very pliable soles. Sometimes when I sit for long periods of time like on the airplane or at a conference, my feet swell a bit so the stretch here is key for comfort. Plus these have no metal bits so I can keep them on when going through security – I keep forgetting that my favorite loafers always set off the metal detectors! I will say the Point style that I’m wearing has the least amount of support out of their styles, so if that’s what you need, check out their sneakers or even their loafers for a tad more support.

2. Loafers

how to style loafers for the office

Sam Edelman loafers 5.5 (also sold here), Reformation tank xs, J.Crew sweater blazer (current version), similar jeans,  EP belt xxs and ring, Goyard tote (my review)

These have hands-down been some of my most worn flats in recent years! I like how they look with denim as well as work pants, and they’re very low maintenance to boot. If I scuff up the black color, it’s easy to touch it up or recolor it, and the leather wipes clean more easily than fabric and suede. I’ve toyed with the idea of a trendier, chunkier sole loafer over the past two years now but just haven’t found the right pair yet!

3. Neutral Pointed Flats

work outfits without heels

Sam Edelman flats (current versionsimilar), Express pants 00 short, Everlane button up sz 00, Quince sweater xs, Sole Society bag (SIMILAR)

Because these flats have more structure and a firmer sole, they are not as soft and comfortable as the other 4 styles listed below, but I do reach for them often when I want a more formal, classic look.

I’d choose a hue similar to your skin tone for max versatility (whether it’s a lighter almond or a deeper brown), and while I used to always prefer a pointed toe for an elongating effect, I have been loving the comeback of round toe ballet flats and even slightly squared off toe shapes. I’ve been eying these M.Gemi flats for a while with a small hidden wedge for comfort, and wish they made more colors! Not sure if this still code works, but you can try JEAN60 there on a first purchase.

4. White Sneakers

fall casual work outfit with sneakers

A staple for any casual / smart casual office or student wardrobe. I rotate heavily between my Vejas (read my review here) and Everlane sneakers for daily school pick up and drop off, and recently got to try the Madewell ones linked above and really liked them as one more option that’s comfier than Vejas!

5. Slingbacks

business casual outfits with flats

WHBM jeans 00P, similar tank, Bershka blazer xsP (similar), similar shoes here & here or with a block heel

I love the effortless chic feel of a pair of slingbacks with jeans and a blazer. The open back is also nice for comfort if your feet tend to swell or shrink throughout the day like mine do! The shoes pictured above are Edited Pieces samples I’ve been working on that have not been produced, but ASOS has some cute affordable ones that they often bring back in new colors. Also, while these slingbacks are not flats, the kitten heel is pretty low and I love how flattering the deep V cut front is! I ended up getting them in 2 colors over the years and they’ve held up just fine for walking around the city.

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9 Comments

  1. Kate wrote:

    Hey Jean, love your blog. I live in the Boston burbs and always know exactly what size to buy and can explore new stores thanks to you. I have been buying a lot from Express due to your posts. In the past few weeks when I’ve gone to buy from there, I noticed XXS and 00 are not available in their new items. Have you noticed the same thing? I think you partner with them fairly regularly so I was wondering if you have any insight as to what’s going on? In the world that’s so concerned with inclusivity – It’s really devastating to have your size removed from stores time and time again

    Posted 10.24.22 Reply
    • Jean | Extra Petite wrote:

      Hi Kate, I’ve also noticed a lot of recent arrivals have not had xxs / 00 and reached out asking their team if these sizes are being phased out. They replied that they will still be making them, so hopefully it’s just the recent arrivals that have not had these sizes!

      Posted 10.25.22 Reply
  2. Serena wrote:

    What are your thoughts on the sam edelman Laurs lug loafer? It’s a chunkier version of the loraine loafer

    Posted 10.15.22 Reply
    • Jean | Extra Petite wrote:

      I like the look and tried them on a few months ago but the leather was a bit stiff and cut into the feet! Wish they were as soft as their Lorraine loafer.

      Posted 10.17.22 Reply
  3. Tiffany wrote:

    I already have small feet (size 5), but the pointed toe makes them look bigger. My husband said they look like elf shoes! Would a round toe have an adverse effect? I already have short legs. (5 ft, 105 lbs)

    Posted 10.13.22 Reply
    • Jean | Extra Petite wrote:

      Definitely trust your instincts and go for what feels flattering on you personally! What about an almond toe or slightly squared off round toe as a more modern take on a regular round toe that is elongating, but not as elf-like as pointed toe?

      Posted 10.14.22 Reply
  4. DB wrote:

    Jean,
    Would you be able to do a post on business casual wedges? As petite ladies, I’m always looking for work appropriate shoes but with a little bit of height. Thank you.

    Posted 10.13.22 Reply
    • Amy wrote:

      Yes, I second that comment!

      Posted 10.13.22 Reply
    • Jean | Extra Petite wrote:

      I have not tried this pair yet myself, but if I were to do wedges for a business casual office I’d probably do a style like these! I like the 3 neutral colors it comes in, too.

      Posted 10.14.22 Reply

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