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

  • The Fancy Teacup January 26, 2012 at 12:36 am

    I'm with you on ankle boots, I usually try to wear skirts/dresses that fall a couple inches above the knee. Adore your picnic chic blouse and that fabulous watch. x

  • hugstiem January 26, 2012 at 12:51 am

    Btw, I don't think it's so much short legs that are a problem for booties but short calves. I think I remember you posted something once about measuring your leg proportions (it was about finding skirt length) and you mentioned that you have long thighs but short calves? (I apologize if I'm making all of this up.) I have the opposite, short thighs and long calves, and ankle boots are a mainstay of my shoe collection. Cognac ankle booties are probably my most-worn pair of shoes in the colder months (my skin color is the same as yours). It's a good thing too 'cause I can't wear low-vamp shoes at all; my heels and ankles are too skinny, so they never stay on my feet.

    A more friendly pairing in general might be skinnies on the bottom rather than a skirt. The lower contrast the color, the better for the short-calved. For example, the gingerbread/pumpkin-colored skinnies you borrowed from someone once might work well with the brown. I personally like a minidress with booties too.

  • petiterealized January 26, 2012 at 1:23 am

    jean, you look more & more refined and beautiful with each post! I think the ankle booties look great on you. I just don't know that I would've gone w/the same color combination.

  • Jyoti January 26, 2012 at 1:25 am

    Those booties are gorgeous! I actually think the dip in the front helps to elongate the legs, so that would be my suggestion– look for ankle boots that don't end with a straight across line, but rather something that creates a vertical, like the 'v' with the ones you're wearing.

  • Petite-ish January 26, 2012 at 1:26 am

    The Cali (?) sun suits you, you're glowing! As for bootie suggestions, how about a monochromatic look with brown trousers? Just roll em up when you're commuting in flats.

  • Satin And Salt January 26, 2012 at 2:07 am

    you look very pulled together and sassy! I cannot believe you are dressing out of a suitcase!


  • mai January 26, 2012 at 3:07 am

    love this combination. and i wish i could get my hair to look like that!

  • what the shoe January 26, 2012 at 3:09 am

    stumpy- i hate that word, but its the perfect word when talking about ankle boots on short legs. i have the same problem, and there are sooo many cute ankle boots out there 🙁 but you look great in them. think it would also be flattering in brown trousers 🙂

  • CocoMeChanel January 26, 2012 at 3:11 am

    so classy and well put together. i wish I dressed like you more often.
    Like how you wore the sleeves rolled up together. <3 if this is out of a suitcase, I need to take style cues!

  • jeni January 26, 2012 at 3:50 am

    Oh my goodness, bowed legs. I may have an accurate description now for the funky action at my knees. (They bow inwards though.)

    Also, I'm really loving this series, especially as I plan for my trip to DC in a few weeks.

  • Sandra January 26, 2012 at 4:15 am

    I love the outfit. It's so classy!


  • bug January 26, 2012 at 4:18 am

    I have short, stumpy legs too. I also have not found a way to wear ankle boots with skirts….even with dark tights.

  • Carli Alice January 26, 2012 at 5:38 am

    Love this outfit! I only have one pair of ankle boots and they are cut straight across (because I bought them years ago). Is there any way I can wear them without cutting off my legs. I'm only 4'10".

    Love!!! this outfit!Pinned!

  • Carla Krae January 26, 2012 at 6:26 am

    I think sometimes short women worry too much about ankle booties. If you like the shoe and it's comfortable, wear the shoe.

    Bowed legs usually happen with babies that try to walk or run sooner than their bones are ready for.

  • Carin January 26, 2012 at 6:35 am

    You look absolutely amazing. I love reading your blog, you have to many tips and ideas and you dress beautifully. I love that you think about what suits and compliments your body.

    Thank you for daily inspiration 🙂


  • Small Town Gal January 26, 2012 at 8:57 am

    Amazing outfit. Love how you style a classy outfit with an edgy pair of boots. I find it challenging too with ankle boots. I can only wear them with capri pants or skirts(which I rarely wear).

  • My Dressy Ways January 26, 2012 at 9:02 am

    I think the boots look great! I have a pair of chestnut colored ankle boots that come up over my ankles and I was afraid of them cutting off my legs and 'shortening' me some more, but they don't. I've paired them with colored jeans and skirts and they look great. I don't think you have anything to worry about with these. I'd love to see them paired with skinny jeans on you – I bet it's all in your head. 🙂

  • Vicky January 26, 2012 at 9:06 am

    Love the way you paired the gingham top with this outfit! love the entire outfit. I think the boots look great!

  • Tina Zeng January 26, 2012 at 9:36 am
  • Elaine A (TOBeautyReviews) January 26, 2012 at 9:45 am

    Jean, I'm REALLY loving this outfit. To me it has all the elements. The booties are trendy and edgy as you mentioned, the skirt is fresh and young due to the higher hem (not sure I could pull it off 😛 ) the shirt is a touch casual and the blazer dresses it all up! Thanks for sharing your thoughts on how the outfit was pulled together!

  • Janki January 26, 2012 at 9:55 am

    So cute! I'm going to raid my 7 year old son's closet now for shirts. A few quick questions: can you do a step by step tutorial of how you roll up your blazers/shirt sleeve? This looks perfect but when I do it, it's all a big mess. The skirt is really short but looks so perfect! I like the mixing of black/brown too.

    On a random side note, when I was in college I took a Japanese film class and one of the director's we studied (Itami) always had his wife in the films. I remember our teacher saying how you can see how much he loved his wife in how he captured her in film. These pictures, if taken by your boyfriend, really do capture a sense of grace and beauty.

  • Karmela January 26, 2012 at 9:58 am

    I've been searching high and low for a pair of booties this low in the ankle, this high in the heel, this brown, and in my size (4). None yet. On a good note, I found a similar gingham shirt at Marshall's the other day, PXS, Calvin Klein, $25! Also comes in pink-and-white gingham combo. Before I started reading your blog I would have passed right on by this shirt, but now you've shown me how to work gingham.

  • CynthiaC January 26, 2012 at 10:23 am

    I don't consider my legs short for my height, but I almost never wear ankle booties with skirts because I worry about it cutting off. I might try it now, especially non-black ones! 🙂

  • Laura Frost January 26, 2012 at 10:50 am

    I have the same problem with ankle boots, but I think you pulled it off to make your legs look long and lean anyway.

  • dietingfashions January 26, 2012 at 11:10 am

    Stumpy legs are also a problem for me. I always imagine the right pair will elongate my stems, but it's also the clothing that matters too.

    Have you tried a Boho look with those ankle booties? I think having a midi skirt and a loose fitted top that's belted will give a fun, weekend look.

  • Michelleesque January 26, 2012 at 11:13 am

    I have the same problem with ankle boots, especially since I have really muscular calves. If it hits any higher than my actual ankle, it'll make me shorter than I already am. I love your entire outfit. Kudos for being able to make so many amazing, well put-together outfits just from your suitcase!

    Michelle of Michelleesque

  • Love and Company January 26, 2012 at 11:15 am

    the gingham shirt combo looks great on you. Booties are the toughest to wear sometimes… Thanks for the tips

  • 7eventh Letter January 26, 2012 at 11:25 am

    This look is so cute. I have to try it. Oh and I am going to try your method of shopping in the boys department for a Gingham shirt, because I have been on a hunt for one forever.

    7eventh Letter

  • Rachels Lookbook January 26, 2012 at 11:33 am

    Great outfit! Super adorable and I'm in love with your booties!

  • Nicole January 26, 2012 at 11:49 am

    OMG that blazer is fantastic. I think it's so versatile. I love the way you have styled this item!


  • DSK Steph January 26, 2012 at 12:25 pm

    Love the look! The checkered shirt is really cool! 🙂

  • Erica January 26, 2012 at 12:52 pm

    I have short legs and large calves, so I avoid booties like the plague! 🙂 Boy is it unflattering on me. It has a way of making me look fat when I'm not. So I only wear them under pants. However, it appears to work fairly decently on you, since you're wearing a short skirt, and your calves are reasonably slim. Overall, though, I'm not a fan of this bootie trend.

  • The_Leather_Skirt_Blog January 26, 2012 at 12:56 pm

    Cute. Cute. Cute. In every sense of the word.

  • Anonymous January 26, 2012 at 1:14 pm

    I think those boots look pretty good styled with the skirt and the gingham, although they look exceptionally good paired with legging jeans 🙂 Also, while your grandma is (I'm sure) super sweet, you have enviable legs (ankle boots or otherwise) so, don't fret 🙂
    On an alternate note, since you feature them regularly, is there any alternative bootie with a similar heel height and look you could recommend? I have tried several times to find those adrienne v. booties in black or brown but they are always sold out in my size (5.5, and 6). I considered ebay, though I have never tried on a pair, so I am nervous about fit, i.e. need to have the option to return. Suggestions?? (please!)


  • Anonymous January 26, 2012 at 1:36 pm

    I personally hate ankle booties and think they are one of Fashion's most hideous creations…. but somehow you make them look good!

  • newpetite January 26, 2012 at 1:49 pm

    Im in the same boat! It makes me look so short 🙁
    You look gorgeous here! Very polished and chic! The booties also go well with the skirt!

  • Marjukka January 26, 2012 at 1:50 pm

    I love your outfit, the gingham shirt is refreshing and the pearls so cute!

  • Jackie January 26, 2012 at 2:40 pm

    I do my black booties with a dark bottom. I don't have another color at the moment but I suppose I would do brown or beige with a bare leg.

    I agree with hugstiem, it's about proportion. I don't think I'd struggle too much with bare legs and booties, personally, because from the waist down, I have 3 more in. than the length from my waist up.

  • Anonymous January 26, 2012 at 3:04 pm

    a pencil skirt would go well since your boots have heels? I don't care for the short skirt with short ankle boots. Maybe add gray-textured tights?

    I love the gingham, blazer, and pearls combo – very elegant. I never thought that gingham can be paired with pearls – great idea!

  • Anonymous January 26, 2012 at 3:39 pm

    I think an ankle boot that is lower cut and dips in the front helps with lengthening, but they can be hard to find esp in small sizes. I am trying a gingham shirt thanks to your fabulous blog 🙂

  • fabbylife January 26, 2012 at 3:52 pm

    I like ankle boots with black sheer tights and black dress. Check my pictures…..

  • Genie January 26, 2012 at 4:02 pm

    You're right, ankle booties do make shorter legs look stumpy, at least mine do. I think you look fantastic though, the skirt and blazer are such a great combo! Maybe finding booties with more of unique kind of cut to them, like yours would help.


  • Ale January 26, 2012 at 4:07 pm

    I wear my ankle boots for the office with nice skinny pants from Ann Taylor. Also with pencil skirts and pantyhoses.

  • Suzy January 26, 2012 at 4:07 pm

    i absolutely adore your outfit!

  • Anna January 26, 2012 at 5:13 pm

    I love this short on you! I agree that this skirt would probably not look very good with a lot of volume on top, but this works just great!

  • Anna January 26, 2012 at 5:14 pm

    Shirt. Sorry 🙂

  • Lusine January 26, 2012 at 6:47 pm

    you are very pretty!)

  • May January 26, 2012 at 7:54 pm

    Don't feel bad about not tanning – tanning is your skin crying for help. You don't want skin cancer!

  • Pauline January 26, 2012 at 11:53 pm

    I've been sporting my cognac booties with semi-opaque (less than 40 denier?) black tights. I find the contrast less stark than pure black tights or bare legs, which isn't to say you can't do either of those options. For visual sake, here's an idea of an outfit, bearing in mind the boot colour isn't truly brown:

  • Juliet'sMom January 27, 2012 at 12:58 am

    love the outfit! great balance of casual and chic w/o looking like you're trying at all. and conveniently, a similar outfit (same upper portion, woll mini bottom) by the (in)famous Really Petite

  • 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?

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

    This comment has been removed by the author.

  • 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.

  • Candy January 27, 2012 at 1:15 pm

    This comment has been removed by the author.

  • Candy January 27, 2012 at 1:16 pm

    I really love your style! So beautiful petite!

  • MrsLord January 27, 2012 at 2:02 pm

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


  • 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!


  • april January 27, 2012 at 7:41 pm

    Love your boots…this style look sophisticated and polish

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

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

  • 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!!

  • 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.

  • 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?…

  • 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.


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


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  • cagnolino January 29, 2012 at 6:08 pm

    wanna visit my blog???

  • Anonymous January 30, 2012 at 11:18 pm

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

  • Ester Ulaya January 31, 2012 at 6:09 am
  • 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?

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

    love that blazer! follow each other?


  • Chocolate, Cookies &amp; 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.

  • 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! 🙂

  • LPFashionPhilosophy February 4, 2012 at 9:52 am

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

    ox from NYC!

  • 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! (-:

  • 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

  • True February 10, 2012 at 5:59 pm

    This is sooo sophisticated look! love it!

    – True

  • Scarlett February 19, 2012 at 12:28 am

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

Comments are closed.