Style in a Suitcase, Part 3: Black, browns + ankle boot woes

This is a scheduled post. I won’t be able to answer any questions until I return. Thank you for reading!


Gap Boys Gingham Shirt sz S – now $12 (boxy fit photos) (navy version), Theory blazer (similar)
Nordies Rack pearls, YesStyle skirt (old), Adrienne V. booties, H&M; bag & belt, Michael Kors watch

I wish ankle boots weren’t so challenging for shorter legs, because I love the bit of edge they add. An easy, elongating way for petites to do the ankle boot is to pair black booties with dark bottoms or tights (see oldie). If you want to go bare-legged, try shorts or dresses/skirts with higher hems to make up for the leg line being truncated at the ankle. I find this latter look to be so chic, but acknowledge it’s less flattering on short legs (and bowed – to this day Grandma laments not “straightening out my knees” before it was too late, whatever that entails).

When I initially purchased these cognac booties online, I pictured them to be lengthening against tanned legs. Wishful thinking! Once I put them on, I was hit by the realization that my skin is not and will never be close to a chocolate color. Aside from the simple dark skinny jean, I was stumped about how to wear these boots without appearing stumpy…

ginghamcamel1After much trial and error, I ended up with a few pairings that were acceptable but not great. I tried a deeper brown (combo shown here) and a dark olive. I also took inspiration from J.Crew and tried a heathered gray tight (to be shown soon), which is fun but not for everyone. Lastly, I tried these boots with skirts of various lengths, and each pairing looked frumpy dumpy except with my shortest, neutral-colored miniskirt shown here.

Keeping the top half sleek was also important. I tried this same skirt + bootie combo on with my chunkier mustard cardigan and boxier tweed jacket, and both looked top-heavy and not so great. Thankfully, I packed one basic black blazer to stay warm in for dinner. 

You can easily convert this outfit for the office by replacing the mini and ankle boots with a longer skirt and pumps. Gingham has the reputation of being a casual fabric (or more commonly, a material for men’s button-ups), but each time I’ve worn it to work I’ve received a number of compliments and inquiries. If you work in a conservative environment, just keep the colors simple and conceal most of the pattern under sleek suiting separates.
Readers – I’d love to hear your ideas (or see links) on other ways a short-legged girl can style non-black ankle boots.

77 thoughts on “Style in a Suitcase, Part 3: Black, browns + ankle boot woes

  • Reply Canadianpetite January 27, 2012 at 2:30 am

    Very classy Jean! Ankle booties for short legs work if you have a mini-skirt on which means it's a no go for work. The only other way I've worn mine is with pants and what a shame to cover it up, right?

  • Reply Anh Anh January 27, 2012 at 9:29 am

    This comment has been removed by the author.

  • Reply Anh Anh January 27, 2012 at 9:32 am

    You said change boots to Pumps, you don't think these type of boots are appropriate for work? I
    Think the pair you are wearing just perfect for work. Don't you think?
    Btw, love your blog as always.

  • Reply Candy January 27, 2012 at 1:15 pm

    This comment has been removed by the author.

  • Reply Candy January 27, 2012 at 1:16 pm

    I really love your style! So beautiful petite!

  • Reply MrsLord January 27, 2012 at 2:02 pm

    This look is so perfect and polished! I love it.


  • Reply Natasha Fatah January 27, 2012 at 2:27 pm

    I think you're being way too critical, this outfit IS great and you do look fantastic. I don't think they make you look stumpy. I think it depends on the body shape of the petite frame. You have long legs, so that's why these boots work on you. I say pair them with a nice flowy, floral dress, that has a mermaid hemline (short in the front, long in the back) and I think you might be surprised by how great you'll look!


  • Reply april January 27, 2012 at 7:41 pm

    Love your boots…this style look sophisticated and polish

  • Reply Alejandra Palestino January 27, 2012 at 9:52 pm
  • Reply CzechBlondýn January 28, 2012 at 1:49 am

    Beautiful outfit.Perfect combination of colors.It looks very, very well indeed.Amazing.

  • Reply Katherine January 28, 2012 at 12:00 pm

    Hi Jean! I know you are in the finance industry, and while I'm still in college (majoring in accounting) I'm trying to explore my options! If you don't mind me asking, what field of finance are you in? Consulting, i-banking, etc…thank you!!

  • Reply Annabelle January 28, 2012 at 5:27 pm

    That outfit is supercute all around! I think you made really good use of the ankle boots, and the gingham looks shockingly snappy with the blazer.

  • Reply Anonymous January 29, 2012 at 2:27 am

    How do you pick and chose what to buy from YesStyle, as many of their items are one size?…

  • Reply Audrey Chrysalis January 29, 2012 at 3:49 am

    First time commenter.

    I have a pair of ankle boots that took me about 5 years to find. What you need to look for is a close fit. The boot needs to hug the foot tight. Any ease and it ups the stump quotient. Also if you can, look for a boot tut is cut below the ankle bone on the side. That is more flattering. For the record I'm 5'2.


  • Reply Classic Glam Blog January 29, 2012 at 3:37 pm


    Please, check out my page, and follow if you like! I'm a newbie, so your support is both needed and appreciated!


  • Reply cagnolino January 29, 2012 at 6:08 pm

    wanna visit my blog???

  • Reply Anonymous January 30, 2012 at 11:18 pm

    I was wondering where you got your boots and if I can still get them!

  • Reply Ester Ulaya January 31, 2012 at 6:09 am
  • Reply Anonymous January 31, 2012 at 4:11 pm

    I saw in one of your old blog posts that you mentioned your mom's cooking blog.

    what is the link for it?

  • Reply Ms.Fashionista January 31, 2012 at 7:02 pm

    love that blazer! follow each other?


  • Reply Chocolate, Cookies & Candies February 1, 2012 at 6:49 pm

    I bought a pair of custom made taupe/dark beige ankle boots (similar to Isabel Marant dickers) because they're the only leg lengthening ones that work on my 5'2 midget self. So far I haven't managed to make anything darker than that look remotely good on me.

  • Reply Annie February 4, 2012 at 6:22 am

    I don't think those booties make your legs look stumpy at all! I think that because the opening of the boot is shorter near the front, it actually lengthens it a bit! 🙂

  • Reply LPFashionPhilosophy February 4, 2012 at 9:52 am

    So pretty! Adore the way you've layered this! Following you now!

    ox from NYC!

  • Reply Cindy Eliza Vaz February 6, 2012 at 8:20 pm

    I'm 4"9 and I have always had trouble wearing booties with skirts! Always felt like they make me look even tinier. How did you pull it off so effortlessly? LOVE your attire combo! (-:

  • Reply ღ Caroline♔ February 10, 2012 at 2:58 am

    I have to disagree with you (very rarely do I ever) on booties…they are far from making your legs appear stumpy! You have such nicely shaped legs and pull off the bootie look so effortlessly! You needn't worry one bit 🙂 Once again, looking so classy like a busy, successful working professional independent woman! <3

  • Reply True February 10, 2012 at 5:59 pm

    This is sooo sophisticated look! love it!

    – True

  • Reply Scarlett February 19, 2012 at 12:28 am

    Jean, I've always wondered how to keep your belt from slipping away from your skirt…

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