Favorite Fall Outfit Ideas for Work & Casual Wear

Happy Friday! We’re enjoying a stream of visitors this month – I always say it, but this is one of the most amazing times to visit New England. The foliage, the orchards, the smell of cider donuts…ahhh. I wanted to share some of my favorite Fall outfits over the years that can easily be re-created. Several of the pieces here are back in stock this year, or I’ve found options that look pretty similar. I like thinking of outfits formulaically, since it makes getting dressed in the mornings so much quicker!

1. Outfit formula: solid tee + puffer vest + plaid scarf + cold weather boots
Get the look: lightweight down vest (wearing navy in xs), blanket scarfduck boots. Nick’s sweater is also still in-stock!

fall couples outfits apple picking

2. Outfit formula: drape cardigan + patterned button-up + skinny jeans + ankle boots
Get the look: fleece wrap (mink in xxsp), gingham shirt, similar jeansankle boots

taupe and gingham

3. Outfit formula: check shirt + navy pants + leopard print accent + cropped trench
Get the look: gingham shirt, similar leopard loafers, navy pants, similar swing trench

morning meeting

4. Outfit formula: stripe turtleneck + scarf + coated skinny jeans + wool hat
Get the look: similar tee, ASOS scarf, similar jeans w/short inseam + similar hat

napa valley fall outfit_scarf hat prada saffiano cuir

5. Outfit formula: patterned swingy skirt + mock neck sweater + suede shoes
Get the looksimilar plaid skirtsimilar cream sweaterCole Haan boots. Maison Jules came out with a very similar skirt this year except a little shorter and less full. Substitute in suede pumps for the OTK boots in order to make this look office-appropriate!

fall outfit - plaid circle skirt sweater boots

6. Outfit formula: plaid pencil skirt + turtleneck sweater + long cardigan
Get the look: similar skirt in gray, similar turtleneck sweater, similar long cardigan

work outfit ann taylor skirt long cardigan

7. Outfit formula: utility jacket + black skinny jeans + tennis shoes + stripe tee + camel scarf
Get the look: similar utility jacket, J.Brand jeans, Nike Free sneakers, similar scarf

nike free sneakers casual outfit boston

Which look here is your favorite? : )


39 thoughts on “Favorite Fall Outfit Ideas for Work & Casual Wear

  • Reply Jessica Burrell October 14, 2016 at 4:37 pm

    Hi Jean,

    I've been a long time looker of the blog, new commenter! I am similar sizing to you; 4'10, 32-26-34, BUT I have a very short inseam, like a 24ish. I always have to fold LOFT skinny jeans etc under about 1.5-2 inches. So they are never as skinny as they should be!

    Do you have any recommendations for very skinny jeans (so they still look skinny?) and also jeans that aren not high rise? I would have jeans up to my neck if I bought a rise of 10 inches! I always look for lower rise so they rest slightly above or right below my belly button.

    Also, check out these booties (they are a dupe of your booties with a dip/slit in the front) I actually bought this pair & cut off the fringe so they look more streamlined. The 5 fits me perfectly & I feel elongates my legs if I cuff jeans.


  • Reply Anonymous October 14, 2016 at 4:55 pm

    Outfit 5, Sweater, skirt and Boots, and not just because of the croissant 😉
    I love both the color and textile combination, and you can build on the outfit, with a coat or jacket, and you can alternate between the OTK boots and tights with heels or flats. So you can get a lot of wear out of the combination. Finally I just love pearls, and the earrings are just adorable in this outfit <3

  • Reply Jessica Cristina October 14, 2016 at 5:20 pm

    Just discovered your blog. Love your outfits! I too am going to New England in a couple of weeks. Can't wait for the weather and just getting away from NYC for a couple of days. Please check out my blog if you can <3

  • Reply La Bijoux Bella | by mia October 14, 2016 at 5:21 pm

    All beautiful looks! Simply always looking fabulous! 🙂

    La Bijoux Bella | by mia

  • Reply Briana Nicole October 14, 2016 at 5:32 pm

    I am so in love with your outfits! Great pictures girlie!


  • Reply Mei October 14, 2016 at 5:34 pm

    TGIF! What a great flashback Friday post! I really like the stripe turtleneck, scarf and coated skinny jeans look. The outfit looks very cozy & chic 🙂

    Pieces of Mei

  • Reply Laticia Correa October 14, 2016 at 6:03 pm

    So many adorable outfits.. How could I choose?! What size Hermes belts do you purchase?

  • Reply MyHanh October 14, 2016 at 6:51 pm

    Number 7! This was smartly done, Jean.

  • Reply Stef October 14, 2016 at 7:04 pm

    Love that last outfit best, but they're all great! I'm heading back to Boston after moving in May and I'm very excited about being there in the fall and having cider donuts 🙂

  • Reply Julia Mazzucato October 14, 2016 at 7:13 pm

    That outfit with the gingham shirt and coat is probably my favorite from your blog. Love all of these fall looks!
    Julia // Little Miss Haute Couture

  • Reply Jessica | Petite Style Script October 14, 2016 at 7:45 pm

    Hi Jean, great round-up of some of your best fall casual/work outfits! I remember the original posts of these and they are classic outfits. It was a touch decision, but my favorites are #2 and #3; I purchased the Bobeau fleece wrap upon your original post & love classic Banana Republic Sloan pants with gingham for a casual Friday work outfit!

    Thank you reminding me of some favorite fall outfits 🙂

  • Reply The Life You Love Blog October 14, 2016 at 8:01 pm

    I am seriously loving all of these outfits! Fall is absolutely my favorite season for fashion, and this is why. You can put together so many cute, cozy outfits.

  • Reply Annie Sun October 14, 2016 at 10:53 pm

    Thanks to this post I just bought myself all from Jcrew Factory – a Gingham shirt, a wool deep burgundy pencil skirt, and a navy quilted vest. Amazing post as usual. Thank you!

  • Reply emch3ng October 14, 2016 at 11:13 pm

    Hi Jean! My favourite outfits were #3, 6, and 7 🙂

  • Reply Manavi October 15, 2016 at 1:04 am

    All the outfits look great to me but I'm in love with the plaid skirt look. I like the black one you are wearing more than the grey one in the link. Great post for Fall. Taking some styling tips from it. 🙂

  • Reply Caroline October 15, 2016 at 1:40 am

    love them all~ you always dress classy yet fashionable!

  • Reply Hanna October 15, 2016 at 2:40 am

    I just love the plaid skirt with a white turtleneck! Saw it I pinterest a while ago and had to save it!! You always look so beautiful and put together!

  • Reply Stylpasja October 15, 2016 at 3:16 am

    inspired me! 🙂

  • Reply Girl About Columbus October 15, 2016 at 8:14 am

    You are adorable!


  • Reply Unknown October 15, 2016 at 9:46 am

    Love your style so much! You look amazing in every outfit you post!

  • Reply Carmen Palacios October 15, 2016 at 9:46 am

    Love your style! You look amazing in every outfit you post!

  • Reply Ev October 15, 2016 at 12:13 pm

    Love the first photo!


  • Reply Peppermint Dolly October 15, 2016 at 12:35 pm

    Your closet is amazing – genuinely love all of these looks!!


  • Reply mybeautrip October 16, 2016 at 11:03 am

    These leopard loafers are a must!


  • Reply Kelsey Quackenbush October 16, 2016 at 7:44 pm

    These fall outfits are so cute!
    Xo, Kelsey

  • Reply One Stiletto At A Time October 17, 2016 at 4:03 am

    The first pic is so super cute!!!

    XoXo One Stiletto At A Time

  • Reply Julie Hiller October 17, 2016 at 11:02 am

    All of these fall looks are so stellar, and that pick of you and Nick is too cute.

    Style by Joules

  • Reply NyFifth Apparel October 17, 2016 at 2:39 pm

    Love every outfit on this blog post! Stripes and plaid are a must-have when it comes to building your wardrobe for the Fall.

    Love your blog!


  • Reply DressedToCode October 17, 2016 at 5:06 pm

    I successfully had a pair of jeans hemmed (free!) and tapered ($10) at Madewell, and you wouldn't be able to tell from the outside. Good luck with your denim search!

  • Reply Joanna Marie October 18, 2016 at 9:27 am

    Try TopShop Leigh skinny jeans. You can order in a shorter inseam! Good luck!

  • Reply Jean October 18, 2016 at 1:37 pm

    Agree with TopShop and would recommend the Jamie cut which I've posted about a few times. If you can find in the petite inseam (usually labeled 28 length even though it actually measures much shorter), they are usually very tapered at the ankle and a little too short for me in the petites, so might be perfect for you!

  • Reply Jean October 18, 2016 at 1:38 pm

    I think I have to agree with you! And a good croissant never hurts : )

  • Reply Jean October 18, 2016 at 1:40 pm

    Hi Laticia! Mine's about 23mm wide. As for length, they didn't have a size that fit so I got it re-sized which is complimentary when you purchase at the store.

  • Reply Jean October 18, 2016 at 1:41 pm

    Perfect layering pieces! I haven't tried the No 2 wool pencil skirts yet from J.Crew Factory. Let me know how it works out and if you know how it compares to the regular J.Crew ones!

  • Reply Soprano2 October 19, 2016 at 1:48 pm

    I like that way of thinking about outfits. I usually think about what colors I can combine and how the styling of different pieces will look when they're put together; this is a great shortcut. I've found that using good accessories well can pull an average outfit together and make it great. I love your look, it's so stylish. I would wear most of your outfits myself.

  • Reply 4Styler Fashion Forum October 20, 2016 at 9:14 am

    Hey, darling! Love your fashion! Wanted to use one of your photos from the blog on our forum – to illustrate how awesome petite girl can wear OTK boots (Pic #5, the outfit formula: patterned swingy skirt + mock neck sweater + suede shoes), but there is incorrect link there… Sorry for mention it… I am going to search your blog in this way 🙂

  • Reply Hadassah Nay October 20, 2016 at 3:55 pm

    Amazing looks all over!!

  • Reply Hip Teacher Mama October 21, 2016 at 9:13 am

    Love your style as always! Key pieces and classic style. Big fan here with three little girls from Ontario, Canada. Great job!

  • Reply Eboni Riche October 21, 2016 at 11:42 am

    I absolutely love all these outfit ideas! For anyone interested in the Marina OTK boots, thought I'd share that Cole Haan is currently running their fall promotion with 30% off!! Nordstrom will also price match if you place your order by phone 😉

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