Fall office style // Olive jacket + tweed pencil skirt

stylish fall work clothes_ann taylor macys petite fashion

I’m a creature of comfort, and this knit tweed skirt does not sacrifice that. It’s thick, stretchy, and lined, with an elasticized pull-on style waistband. I’ll be wearing this one through much colder weather, with tights!

womens workwear fall style petite tory burch small york tote bag

Measurements of this skirt in size 00 petite, when lying flat and un-stretched: 13″ across the waist, 15.5″ across the hips, 22″ total length. Note the material is very stretchy. Although this skirt fits me better off the rack than most AT skirts, the waist is still a little loose when worn at my high waist, so I’ve cinched it here with a wide belt.

Other Ann Taylor picks

black work handbag laptop tote tory burch york purse
classy outfits tweed petite pencil skirt olive trench coat

Olive Swing Trench

I am so stoked about this olive cropped trench find from Maison Jules! Use code VIP for extra 30% off, making this half off its original price. The sleeves are long on me, so I’ll have to get them shortened. The shoulders fit well, though, which is more important and saves quite a bit in tailoring. The material of this is like a thick crepe fabric (jacket is lined), and looks more high end than its price tag, in my opinion.

An alternative jacket on sale is this olive knit open blazer, also by Maison Jules. This one fits on the smaller side with 3/4 length sleeves – the regular xxs blazer works on someone my size with no alterations needed!

boston fashion blogger back bay shopping

Classic WOrk Tote

I recommend my small Parker tote (comes in lots of pretty colors) as an everyday work bag, for those who have laptops on the smaller side. This tote is roomy enough to fit my Macbook, shoes, and more, without being too heavy or overwhelming my frame. The leather feels similar to coated saffiano leather and is easy to wipe clean. It has a zippered top, and I especially like the large front slot with a magnetic snap closure for easy access.
tory burch handbag york black laptop work purse

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  1. Maia wrote:

    Perfect. Love your set. Thanks for the post

    Posted 10.18.17 Reply
  2. Miki wrote:

    Hi Jean! I am a big fan of your blog and I constantly follow your tips. I recently purchased the Banana Republic Avery-Fit Pants and I plan to shrink it in my dryer, just like you did with your Sloan-Fit Pants!

    However, given that the fabric of the Avery-Fit (wool and spandex) is different from the Sloan-Fit (viscose, cotton and spandex), do you think shrinking it in the dryer will work?



    Posted 10.6.17 Reply
  3. Leslie P. wrote:

    Picked up this jacket and got the extra 30% off! Would absolutely agree on the quality of the jacket, the material is great and it also has some movement so it’s not so stiff. I already had a very similar skirt in my closet which needed a great layering piece and this was perfect!

    Posted 9.25.17 Reply
  4. Wow looking gorgeous …

    Posted 9.25.17 Reply
  5. Ariel wrote:

    Hi Jean! Beautiful outfit! How big is your MacBook & how heavy does the tote end up being? I’m looking for a new workbag but I have a 15inch work MacBook. Thanks!

    Posted 9.22.17 Reply
  6. Love this! But how do you keep your belts in place without belt hoops? I hate adjusting things all day…

    Posted 9.21.17 Reply
    • Jean | Extra Petite wrote:

      Hi Cathy – they will definitely shift if you don’t add anything to secure it, and even then it can be a bit of a pain to adjust. Pasting in my answer from above:

      I love wearing belts, so sometimes I have my tailor add small threaded loops to some skirts, also, double-sided fashion tape helps! If it’s a small / narrow belt, I have also used large safety pins as “belt loops” on the side seams of my skirts.

      Posted 9.21.17 Reply
  7. Mimi wrote:

    Lovely skirt and I love the whole outfit too! Beautiful pieces and they’re working well together. 🙂

    Have a nice day,


    Posted 9.20.17 Reply
  8. Ann Marie wrote:

    honestly, I think Macy’s only produces 1 jacket in XXS! By the time you post & I look for the item online, they no longer carry it in XXS 🙁

    Posted 9.20.17 Reply
    • Jean | Extra Petite wrote:

      Oh nooo … I swear, they probably just make a small handful : ( So frustrating!

      Posted 9.21.17 Reply
  9. Those pumps look like they really lengthen the legs – very petite-friendly, I love it! <3


    Posted 9.20.17 Reply
  10. Made in Mauve wrote:

    Love the jacket!

    Posted 9.19.17 Reply
  11. Miranda wrote:

    How do you get your hair at the top of your head to look so voluminous? My hair is always so flat (I have a naturally oily scalp)

    Posted 9.19.17 Reply
    • Jean | Extra Petite wrote:

      Hi Miranda – I spray texture spray on it (using shu uemura dry texture finishing spray). after pulling my hair back into a ponytail and securing it with an elastic, I then always tease some out at the top to form a bump with my fingers.

      Posted 9.21.17 Reply
  12. I love this color for fall! Olive is such a beautiful shade.
    Julia・Little Miss Haute Couture

    Posted 9.19.17 Reply
  13. Sharan wrote:

    Love your ponytail in this look!!


    Posted 9.19.17 Reply
  14. Jae wrote:

    Beautiful olive jacket!

    Posted 9.19.17 Reply
  15. kim wrote:

    You look great as always, but I am especially coveting that bag. It is the perfect size for a petite frame whereas totes often seem to run large and overwhelm. Great find.

    Posted 9.19.17 Reply
    • Jean | Extra Petite wrote:

      Hi Kim – thank you!! My thoughts exactly regarding the bag … it’s been a challenge to find bags that fit my laptop, shoes, and other junk without overwhelming a shorter frame!

      Posted 9.21.17 Reply
  16. Carissa M Lee wrote:

    I love this green on you! How do the sleeves look folded up in the interim?

    Posted 9.18.17 Reply
    • Jean | Extra Petite wrote:

      Hi Carissa – thank you! They look normal folded up (ironing the fold and then using double sided tape to secure it always helps), but i’ll definitely need to get them properly hemmed soon!

      Posted 9.21.17 Reply
  17. The olive/military green color reallyyy stands out subtly. Loveeee especially the belt!

    Posted 9.18.17 Reply
  18. Elizabeth wrote:

    I’m loving that olive jacket so much! <3 🙂 Such a great and easy way to incorporate fall colors in to the office wardrobe! And your skirt is gorgeous!

    XO, Elizabeth

    Posted 9.18.17 Reply
  19. Jody wrote:

    Tutorial on this hair style please?


    Posted 9.18.17 Reply
    • Jean | Extra Petite wrote:

      Hi Jody – I just made an updated hair curling tutorial (hopefully it’ll be on the blog within 2 weeks), and all I did was take that curled hair and sweep it into a low ponytail. I always finish my ponytails by wrapping a small piece around the elastic : )

      Posted 9.21.17 Reply
  20. Liv wrote:

    So professional and chic!



    Posted 9.18.17 Reply
  21. Katerina wrote:

    Always stylish, elegant and so feminine! 🙂


    Posted 9.18.17 Reply
  22. Jen wrote:

    Hi Jean, I have been following your IG for a couple of months now. I have to say that you have given me so much inspiration for my wardrobe. Your outfits are always so classy and elegant. I love your ideas and outfit ideas. Thanks for sharing!

    Posted 9.18.17 Reply
    • Jean | Extra Petite wrote:

      Hi Jen – you are so sweet. That means a lot to me to hear – thank you!

      Posted 9.21.17 Reply
  23. mayu from JAPAN wrote:

    Hi, Jean! I always thank you for your trusty recomendations 🙂

    The pieces I purchased online today are…tweed pencil skirt, ruffle cuff sweater with crew neckline, grey bow pumps, marled puff sleeve sweater, black pencil skirt with slit, olive jacket from your picks.Can’t wait to wear them!

    Posted 9.18.17 Reply
    • Jean | Extra Petite wrote:

      Hi Mayu – you picked some great pieces! : ) I hope you love them! I’m sorry the olive jacket got cancelled : /

      Posted 9.21.17 Reply
  24. Isabelle wrote:

    Wow Jean! That outfit is so elegant! Too bad the sale at AT is only for US and Macy’s doesn’t ship to Canada yet because I would have bought it! I will definitely look for similar items here 🙂

    Posted 9.18.17 Reply
    • Jean | Extra Petite wrote:

      Thank you, Isabelle! It’s such a bummer about AT sales always being US-only, and I didn’t realize Macy’s doesn’t ship internationally : (

      Posted 9.21.17 Reply
  25. Michela wrote:

    i love this outfit so much!!
    miki x

    Posted 9.18.17 Reply
  26. Rachelle wrote:

    Such a gorgeous work look, love that skirt.

    Posted 9.18.17 Reply
  27. Kristjaana wrote:

    You look so gorgeous in this classy office look! And totally in love with your hair this way <3

    x Kristjaana

    Posted 9.18.17 Reply
  28. This is such a cute outfit!

    Posted 9.18.17 Reply
  29. I always love your style Jean! That olive green goes so well with the black!

    I hope you’re having a lovely Monday!

    Posted 9.18.17 Reply
  30. Lyla wrote:

    Hi Jean, I’ve been wondering a long time. How do you wear a belt with a skirt without belt loops and keep it in place? For example, when you sit the belt on my back will ride up. Do you have to put it back in place each time you move around? Very cumbersome not to mention can be quite embarrassing to see the belt is up against your shirt instead of skirt when you are seated. Appreciate some tips on how to manage this dilemma I have.

    Posted 9.18.17 Reply
    • Jean | Extra Petite wrote:

      Hi Lyla! There’s no real secret … if you don’t add anything to secure it, the belt will definitely shift around when you sit. I love wearing belts, so sometimes I have my tailor add small threaded loops to some skirts, also double sided fashion tape helps! If it’s a small / narrow belt, I have also used large safety pins as “belt loops” on the side seams of my skirts.

      Posted 9.21.17 Reply
  31. Rena wrote:

    This is the perfect office style and I really like your skirt and how you have styled this classy piece!
    xx from Bavaria/Germany, Rena

    Posted 9.18.17 Reply
  32. That olive jacket is a dream! I love that colour for all year around, but it’s especially beautiful in fall. I love the skirt you’ve paired it with too. You look beautiful.

    Sarah Lilly || The Lilly Mint Blog

    Posted 9.18.17 Reply
  33. My office doesn’t have a strict dress code and I’m thankful, but outfits like this from you makes me wish it does! What a beautiful outfit to feel like a power woman in!

    Charmaine Ng | Architecture & Lifestyle Blog

    Posted 9.18.17 Reply
  34. Marjorie wrote:

    This tweed pencil skirt is so beautiful. Love it!

    Posted 9.18.17 Reply

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