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Wardrobe Pickles

I’ve been getting a shit ton of Cheap JAPtastic emails from you gals as of late, which is all kinds of awesome. Especially when I get two related queries and one ends up answering another. Tres convenient!

Ankle Boot Angst (Did I really just write that? You know you’ve read too many issues of Lucky when…)
i was wondering what your thoughts are on leather boots in the summer/what to wear with them in general. i have these (frye tina shorty cuff boots).

i love them but i don’t know what to do with them because i’m the least fashionable person ever. i read your blog because the only reason i will ever go shopping is if things are on sale/at the outlets and so i love it/you.


A Vintage Query
I have a question about how to style a vintage dress. I bought it awhile ago on and I just absolutely love it. However, I have no idea how to style it.

If you have any suggestions on how to make it look more acceptable for everyday wear, please let me know. I’m also in my mid-20s, and I fear looking too matronly. My ideal balance is classy, but still sexy. The length of the dress falls right to my mid-knee. I’m hesitant for it to go any shorter…


Ankle Booties, meet Vintage Dress. Vintage Dress, meet Ankle Booties. Play nice.

I don’t like to play stylist, because I’m of the mind that you gals can and should wear whatever the eff you want to wear as long as you feel great wearing it. There’s my disclaimer. Alas, your emailing efforts require a non-half-assed response, so here we go.

First off, Alyssa: Those booties are KILLER, so enough of this crap about you being the least fashionable person ever. The point of ankle booties, methinks, is to add a degree of badass to whatever you’re wearing. As long as you’re cool with the bare legs and boots combo, I’d def pair ’em with jean shorts and/or dresses (vintage, or otherwise) in summer. If you’re a shorty like me, keep the hemlines high to avoid any midgetizing effects. And if you’re worried about the slut-factor, opaque, dark tights are an excellent buffer. Straight leg jeans and/or leggings plus ankle booties also equals awesome. If you can embrace the weirdness of this pump/boot fusion and not stress over whether or not you’re stylish enough to pull it off (you are, and anyone who thinks otherwise can go eff off), you’ll eventually come to see these booties as one of the more versatile things you own.

Onto the vintage pickle: Deland, this dress is totally gorge, so well done you. IMHO, hemline surgery is the most effective means of making something more youthful. If you hacked a few inches off this thing, you could go bare legs and flats in summer and/or opaque tights and pumps in winter and never have to worry about the looking-like-a-mom factor. The top part of the dress provides enough coverage to pull off a shorter hem; if the classy/sexy balance is what you seek, I think this is the way to go. (If you’re convinced, get this professionally shortened – it looks waaay too nice to scissor yourself).

If you’re still hesitant, I respect your modesty. Knee-high boots and/or ankle booties are an excellent alternative for modernizing an uber feminine dresses of this ilk. A thick leather belt at the waist might be nice too.

Ladies, best o’ luck with your finds. And thanks mucho for the queries – keep ’em coming.

Cheap JAP



love the boots and they’d go with anything. seriously.

i’d totally play up the femininity of the dress and pair with heels and a jacket (something weird and structured) for work. soft and ladylike with a modern note. good buys all!


1. i adore ankle boots in all their forms and YES once you figure out how to rock them they do become the most versatile thing you own. i bought my first pair 2 years ago and didnt know what to do with them, now i would wear them every single day if possible
2. hot dress, but i would definitely not hem it- you would lose the pretty ombre effect at the bottom and midknee is perfect for walking that fine line between youthful and classy- you can dress with with a cardigan +tights +pumps for work, or with nude shoes & a long necklace for a wedding, or total badass with ankle boots/flats for everyday, kick ass purchases girls!


Those ankle boots are so awesome. I love the cuff. How about a cool graphic tee, blazer, and dark skinny jeans? Or a floral dress and a leather jacket? Ankle boots are so versatile and rock chic. They look great with bare legs so you can rock ’em in the summer.

That dress is gorge. Cheap JAP is dead on about hemline surgery. Think about that dress with some white/cream platform sandals. Or with a pair of nice brown flat sandals, a wide brimmed hat and a denim jacket perhaps?

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