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… 
After 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. 
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 http://instagr.am/p/kiuyu/
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: http://www.hm.com/ca/dressingroom/LADIES?lid=02XPG3-Z6U
Don't feel bad about not tanning – tanning is your skin crying for help. You don't want skin cancer!
you are very pretty!)
Shirt. Sorry 🙂
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!
i absolutely adore your outfit!
http://highprofilehighexpectations.blogspot.com/
I wear my ankle boots for the office with nice skinny pants from Ann Taylor. Also with pencil skirts and pantyhoses.
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.
xoxo,
Genie
http://www.uniqueandchicstyle.blogspot.com
I like ankle boots with black sheer tights and black dress. Check my pictures…..
http://fabbylife.com/2012/01/10/dvf-sweater-dress-materia-prima-fringe-booties/
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 🙂
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!
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.
I love your outfit, the gingham shirt is refreshing and the pearls so cute!
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!
I personally hate ankle booties and think they are one of Fashion's most hideous creations…. but somehow you make them look good!
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!)
Meg
Cute. Cute. Cute. In every sense of the word.
http://theleatherskirt.blogspot.com/
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.
Love the look! The checkered shirt is really cool! 🙂
OMG that blazer is fantastic. I think it's so versatile. I love the way you have styled this item!
whatnicolewears.blogspot.com
-N
Great outfit! Super adorable and I'm in love with your booties!
http://www.rachelslookbook.com
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
http://www.whatsmoreimportantthanfashion.com/
the gingham shirt combo looks great on you. Booties are the toughest to wear sometimes… Thanks for the tips
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
http://www.michelleesque.com
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.
I have the same problem with ankle boots, but I think you pulled it off to make your legs look long and lean anyway.
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! 🙂
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.
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.
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!
you look gorgeous as always!
http://www.tinacious.me/
http://www.tinacious.me/
Love the way you paired the gingham top with this outfit! love the entire outfit. I think the boots look great!
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. 🙂
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).
http://mui28.blogspot.com
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 🙂
/Carin
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.
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!
I have short, stumpy legs too. I also have not found a way to wear ankle boots with skirts….even with dark tights.
I love the outfit. It's so classy!
Xxx
http://www.theblackpearlblog.tk
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.
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!
http://cocomechanel.blogspot.com
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 🙂
http://whattheshoe.blogspot.com/
love this combination. and i wish i could get my hair to look like that!
you look very pulled together and sassy! I cannot believe you are dressing out of a suitcase!
-NIco
http://www.SatinAndSalt.com
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.
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.
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.
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.
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
http://www.TheFancyTeacup.com