ASK ALISON: Are These Boots Too Crazy to Wear?

I heart reader Q's. Keep sending 'em!
Publish date:
August 7, 2013
shoppables, Ask Alison, boots, whimsy, cutesy

A lovely xoJane reader just sent me the following adorable email:

Hi Alison!

In your bio it says that fashion has no rules, and well, I recently bought a pair of boots that seem to break all the rules according to everyone around me.

Everyone says they're crazy looking, in a bad way, but I bought them anyway because they're just so COOL. And now I don't know what to wear them with!

Only two people I know think they're almost as cool as I do, but they don't have any idea of what to do with them!

I have trouble finding clothes that both fit and are cute because I'm really short and busty. I want to rock these boots so badly, but I just don't know where to start.

Please help me!!


The boots! by avf213 featuring side zipper boots

Anna's boots are pretty unique -- a fresh iteration of the famous Lita boot. I think that might be what her pals are balking at. People fear stuff that is weird. But the weird stuff is usually the really cool stuff when it comes to fashion! And who could be mad at a hot pink sole? Someone who kicks kittens, that's who.

I think boots this unique can't be taken too seriously. Whatever you wear with them needs to give a wink and a nod to the fact that you know how zany they are. So every outfit I put together for Anna has a little bit of whimsy and humor to it.

Anna's boots are a great color -- super neutral and quite close to her skin tone, which helps lengthen the leg instead of cutting it off awkwardly. This is a very good thing for a petite girl! They go with almost anything, and they remind me of Katie Holmes' beloved Isabel Marant boots that I wrote about last year.

I think Anna should wear her boots with skirts and dresses as much as possible, because they are most definitely meant to be shown off. They have to be the centerpiece of whatever you pair them with.

Simple smileys! by avf213 featuring a ruched skirt

The simplicity of this tissue soft, peachy colored tee plays off the pink sole of the boots without being too matchy matchy. The smiley bracelet adds in a tiny dose of humor, and the black skirt grounds what could otherwise be too twee of a look. Yes, you can wear black with tan! Contrast is where it's at in fashion, kids.

Florals + watch by avf213 featuring a wrap bracelet

This sweet prairie girl dress is a good antidote to the fierce lines of Anna's boots. A hot pink jumble of a watch ties in the pink soles and gives the eye something extra to take in. The boots make such a statement on their own -- you want to make sure your accessories are equally as exciting.

kitty Kat by avf213 featuring h&m dresses

I love this crazy cat dress when it's paired with some sweet pearl bracelets. Again, the touch of pink in the cat's ears and tongue makes the boots work even though the dress is predominantly black. I find myself sort of wanting to wear this to my upcoming high school reunion. SIKE! I'm never going to a reunion of anything. As if!

Work Style by avf213 featuring suede boots

I think it might be possible to wear these crazy boots to the right type of office job. You just need a dress in a classic cut that matches the intensity of the boots. Screaming yellow does the trick -- and a simple pair of hot pink rose earrings holds their own without pushing the whole look overboard.

Ice Cream & Boyfriend Jean by avf213 featuring boyfriend jeans

A pair of casual rolled-up boyfriend jeans with a simple blouse in a bright color is a good way to tone down the boots without hiding them. (A bright turquoise or brilliant green flowy tank would also work well here!) The ice cream ring adds just the right touch of silliness, making this outfit perfect to wear to a concert or a house party.

Horses, Meet Skinny Jeans by avf213 featuring a charm bracelet

Anna's boots could be worn with any color or print of skinny jean on earth. That's the beauty of a tan suede shoe -- the possibilities are just endless. The ones I've featured above are a bit on the $$ side, but Forever 21 currently has over 200 different pairs of skinny jeans for sale -- all under $30! A super skinny, teetering bottom half needs some balancing out, and a boxy graphic tee does the trick with ease.

Everything I've linked to here is only meant to be a jumping off point. The goal isn't to buy a bunch of new stuff. You may already have something like it in your closet that you can use to style your very own version! My goal is just to give you the spark of an idea -- as well as the confidence to wear the stuff your pals may think is totally crazy.

Because like Anna said, I believe that fashion rules are almost always arbitrary, made up, and above all else, BORING. Crazy is good. Crazy is fun. Crazy is cool. Seek out what makes you happy, gives you confidence, and brings you joy. That's what fashion is supposed to do -- always put a smile on your face, and not ever bring you down.I'm on Twitter: @IveyAlison