Shoes + Pants: A How To.

You could fill a small book with the things I don’t know about fashion. Thankfully, I have friends who know things. Remember when I posted about how my friend Regine Franco taught me the little trick about wearing oxfords with a cuffed pant? Now it seams so obvious to me, but at the time, I couldn’t figure out how make them look good on me, they were just looking weird and making my legs look thick. Anyway, I begged Regine to teach us a little bit about the little details in pairing the right shoe with the right pants and how to style it. (Actually, I ambushed her at her apartment!) The lost art of baring ankles. How you wear something, and with what, is as important, if not more important than the actual piece of clothing. Wearing the wrong shoes, in the wrong way, does something awful: it makes legs look not so hot, and it also just looks slightly off. I know this, because I recognize that I make these mistakes often. Sometimes the individual pieces are great, but when I get home from the event, party or day and catch a glimpse of myself in the mirror, I realize: This looks terrible. And I see people doing weird things with shoes and pants in the street all the time. We all try to work new trends into our wardrobes every year, and it’s not always as simple as it looks.

So, lets begin! We started with the oxford example, but this holds true for any flat shoe, loafer or sneaker that hits below the ankle. (Ballerina flats show skin on the foot so you don’t need to roll your jeans to make that work.)

Isn’t the difference startling? Just the little hint of ankle bone instantly feminizes the masculine oxford and makes legs look thinner and the entire outfit wearable. I was amazed when I learned about this!

Next we styled a classic flat shoe boot with a narrow top with a simple skinny jean. Normally, I just let them bunch at the top of the shoe boot, which is fine looking, and I’ve even seen people do a small cuff above the boot top. It all looks ok. I never even CONSIDERED pulling the jean OVER the boot, but when Regine did it, I couldn’t believe how much better it looked! The whole leg seemed more streamline, very neat and preppy, and the unexpected meeting of the jean with the boot looked very chic and well considered. Love it.

Next she worked in one of the latest trends that I find impossible to style, the high top sneaker. These are flat, not wedges, but I’ve seen varying forms of this everywhere. Again, I never jumped on the trend because every time I tried this on in a store, I felt like my legs looked stumpy. And they did, because the jeans were bunching on top of the high top, creating actual bulk on my calfs – which are NOT fat, and are generally the slimmest part of the leg on most women. Why make myself look short and stumpy for no reason? Better to just skip it, I thought. But once again, Regine’s sleek styling with white jeans, tucked completely down into the boots made the legs look long and lean. Once again, the little details that she considers really makes the entire look sing.

Now we decided to tackle the ubiquitous shoe boot, and the also very trendy track pant. The track pant can go wrong in so many ways, but its universally flattering feature is the elastic bottom which allows for easy ankle baring. The only thing is, YOU MUST show your ankles. It’s not that obvious, I see people who tuck these into boots, and in FACT, I’ve done that. (Uch, I’m terrble.) Any shoe that hits below the ankle will work with this, oxford, sneaker, shoe boot, or pump.

Last, my favorite, the pointy toe pump. Regine says this is the most flattering shoe of all time, especially in a nude, and I cant disagree. For this look, we matched the pointy pumps with a tuxedo pant from Topshop. Because the pants were not the most well made pants in the world, we couldn’t cuff them, and they hit a little long. We agreed that these pants should be hemmed so that the tapered end hits just above the ankle, as we’ve shown it in the picture (we rolled the waist to get them to hit this high). I have to say, I’m so happy that the un-platformed pointy pump has returned… I’ve been waiting for this for about 3 years now, and that non-jegging jeans are coming back too. Thank the heavens.

Anyway, I hope you enjoyed our little shoe/pant guide. I know these things SEEM simple, but as someone who’s gotten wrong, I can tell you, the devil is in the details my friend, and Im about to start worshiping Satan. (I stole that line from this weeks Gossip Girl, but still. Works!)

There are a ton of other things we can tackle: the moto boot, the cowboy boot, the mid calf high heel boot (I think these are ridiculously un-good looking, but I’m willing to be convinced.) Over the knee boots, shoes with ankle straps, I could go on and on about all the trends I avoid because I’m not sure how to wear them!

Anyone else ever have trouble in this department?

And of course, a super big thank you to Regine, one of my go-to style expert friends!

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  1. MMish says:

    love this, post shoe sources!!!!

  2. Brilliant!I have been dying to buy oxfords and now you’ve just solved my problem. wanna go shopping? :)

    also. I am in love with my moto boots but usually pair them with a legging (I know….) or skinny jeans. I’d love to find out how to femme these up.

  3. This is awesome. I thought I was the only having these crazy feelings where I knew something wasn’t right but couldn’t figure out how to fix it! ANd just yesterday I bought some booties and was trying on different jeans to see how I could make them work! Seems so simple….but isn’t! Styling is an art indeed. Very helpful.

  4. I LOVE this post. those shoes are fab. love the high tops and those army green heels.

  5. Lauren says:

    This is a great post and I think you should do a style series like this.

  6. I am so excited I found this article! I have 2 pairs of oxfords that I love but have had so much trouble styling them..I’m a pretty thick, curvy, girl and always end up feeling like I look dumpy and manly. so great fun for the cuff tip…I might also try this with an ankle pant for work!