Fall Outfits Lately with Flats

abercrombie tweed jacket everlane sneakers petite fall outfit

I recently blogged a roundup of practical outfits with flats, and wanted to share a few more from our Fall weekends. I’ve always been a fan of having outfit “formulas” to reference when getting dressed in the AM, and on weekends this is especially helpful since the kids are up bright & early hankering to get outside!

1. Lady jacket or cardigan + ankle jeans + flats

I love this simple combo since there’s so many variations you can spin off of it. Switching out the sneakers for loafers or ballet flats makes this more office-appropriate, or a black ankle bootie (these Stuart Weitzmans on sale look gorgeous!) would be another chic alternative. I went with my structured tweed lady jacket here for more warmth, but I often toggle between this one and my Emilie sweater jacket which offers a very similar, but less formal look.

boston apple picking outfit slim calf rain boots
2. Long Cardigan + Mini Skirt + Layering Tee

A shorter skirt paired with a long layering piece (sweater, trench, etc) is another easy and chic combo. I wore rain boots here for a muddy farm outing, but this same outfit would be cute for a smart casual dress code with a pair of black tights and loafers or ankle booties. You can find my review of this cardigan jacket in this post – truly so versatile!

Quick note on these rubber boots, which were a rec from my friend Wendy. The fit is a little tricky and they’re best suited for someone a tad taller than me (I’m 5′ tall) and with slim calves. I love the sleek equestrian style and the slim calf fit, but note the shaft is higher than ideal for me. The foot area also runs a little small. I’m usually a size 5/5.5 with narrow calves and I am wearing the size 6 here.

Measurements of the size 6 boot: 12.75″ around the calf opening, 14.5″ shaft height when measured along the inner boot, 15.5″ shaft height when measured along the outer boot.

Sidenote – for fellow moms with skirt loving gals, these skirted pants (we sized up) are amazing! Super soft and comfy, easy to pull on & off, and quality is much better than other brands we tried.

3. Blazer + turtleneck + jeans
banana republic camel captains blazer
BR blazer 00P (similar at BR factory), Madewell jeans 24P (hems cut), Mary Jane flats sz 5.5 (added a thin cushion for comfort), similar mockneck, EP mini belt xxs

Since this jacket is longer in length, I like to keep the bottom a little more fitted with slim-cut jeans instead of wide leg.

4. Crop trench coat + ankle pants + Flats
cropped trench coat black pants petite fall outfit
7/8 joggers XS petite, SM crop trench – similar here or here (their kids 12 fits me), similar flats, Polene bag c/o, $15 sunglasses

This is yet another way I’ve worn my Amazon jogger pants which I reviewed earlier this fall. The joggers are a little loose on my waist, but the length is perfect and they’re so comfy for WFH or weekends with the kids. The dressier flat makes this pairing a little more chic, and I’ve also worn this outfit with my Adidas sneakers for a more altheisure look.

When you purchase through the links on this blog, I may earn a commission. Thank you for your support!

When you purchase through the links on this blog, I may earn a commission. Thank you for your support!

For Daily Posts

Leave a Comment


  1. Sophie wrote:

    Wonderful post – the outfits are chic and wearable for real life- not many bloggers can do this. Also your reviews are very useful and thorough. My favourite are: the lady jacket out fit and the cropped trench with the comfy joggers.

    Posted 11.5.23 Reply
    • Jean | Extra Petite wrote:

      Thank you so much, Sophie! I’m so glad you find the reviews helpful xx

      Posted 11.7.23 Reply
  2. Tee wrote:

    Hey Jean, I love your fall outfits here! I am a mom of two young boys and I love the practical shoes you show in your outfits and still look comfortable and put together. Keep the inspiration going, Jean!

    Posted 11.5.23 Reply
    • Jean | Extra Petite wrote:

      Thank you! Practical shoes are definitely a must when chasing two little ones around xx

      Posted 11.7.23 Reply
  3. Sarah-Jayne wrote:

    I love all of these – I know you do outfits with flats a lot these days but please consider making this a series, it’s so helpful to have them all in one post!

    Posted 11.4.23 Reply
    • Jean | Extra Petite wrote:

      Thank you Sarah-Jayne! If you search “outfits with flat shoes” in the blog search box, all of my recent and past posts on the topic should pop up!

      Posted 11.7.23 Reply
  4. Beth wrote:

    I thought your apple picking outfit was lovely, Jean! I’ve noticed over the years that some women make snide comments when they think I’m “dressed up.” It’s silly because a skirt is often just as easy to put on as a pair of sweatpants or jeans and a cardigan is just as easy as a hoodie. Everyone has their preferences, and for me I rarely own a t-shirt because it’s just not “me.” One reason I’ve followed you for years is that you sensibly and beautifully incorporate that “elevated” style that I enjoy. Thanks for sharing!

    Posted 11.2.23 Reply
    • Jean | Extra Petite wrote:

      Thank you, Beth, for the kind note! I agree it’s the same amount of effort to put on a skirt or sweatpants – it just boils down to personal preference, and it seems unnecessary to make unkind commentary on either end!

      Posted 11.3.23 Reply
  5. Anonymous wrote:

    Please tell me your apple picking outfit is just for the purpose of this blog! It looks like you are dressed for work. Really??

    Posted 11.2.23 Reply
    • Jean | Extra Petite wrote:

      Yes, really, I wore that for our family outing and was very comfortable in it. I like looking for ways to incorporate my older pieces like the skirt which aren’t getting enough wear. There’s really no need to be rude if something isn’t your cup of tea.

      Posted 11.2.23 Reply
      • Sophie wrote:

        I think this demonstrates very nicely how a change of shoes can alter the mood of the outfit. I could wear the boots for the walk and then quickly change into some smart ballet flats or even kitten heels for lunch or afternoon tea. Simple!

        Posted 11.5.23 Reply
    • Anonymous wrote:

      What kind of workplace do you work at that makes you think mini skirts and rain boots are work attire??? 😂

      Posted 11.4.23 Reply

Get the newsletter!

What updates would you like?