5 Ways to Wear a Leather Jacket

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Welcome to another episode of “How to Wear.” I’m your host, Sarah. (I’m practicing for my future in the game show industry. With this economy it’s important to have a backup plan.) I picked leather jackets for this one because they’re such a good in-between-seasons layer. In fact, some of these photos are from way back in the fall! Go ahead and drink in the versatility of a leather jacket, my friends.

No. 1…

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There’s something cool about combining a shirt that says “buttoned up” – literally – and a jacket that says “I’m a rebel without a cause.” I’m partial to printed oxford shirts, but I think this would work just as well with a solid.

No. 2…

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Another great juxtaposition: girly and rugged at the same time. I wore this last fall so the brown and black seemed appropriate, but I’d like to try it again this season with a more colorful dress.

No. 3…

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A leather jacket is one of those classics that will never go out of style, so I like it mixed with other classics: jeans, a striped tee, and tortoiseshell shades.

No. 4…

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I don’t know exactly what possessed me to wear a leather jacket with a floor-length flowing skirt and suede heels, but I’m glad I did. If you’re going out in the evening, it can get chilly, so why not try something besides a boring old stole?

No. 5…

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Note that I saved this one for last because if I put it first you wouldn’t have read the other four. I’m tricksy that way. But really – the whole point of this post was to remind you that leather jackets (real or otherwise) are just jackets, and you can wear one with pretty much anything and you’ll probably look cooler than you did without it.

See the original posts for each of these looks: 1 // 2 // 3 // 4 // 5

My jacket is from Express’ “Minus the Leather” line. The jackets come in a variety of styles and colors.

How to Wear Ankle Boots

This post has now been updated for 2014! Click here to see it.

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It’s time for the long-awaited next installment of “How to Wear”! This time I’m talking ankle boots or booties. They’re so darn adorable, but they can be hard to wear. They cut off your legs at the ankle (as you might have guessed), which can make you look shorter, which in turn can make you look fatter. I don’t mean to speak for all women, but I tend to shoot to look more like Gisele and less like Danny Devito. The key to wearing ankle boots is elongating your legs as much as you can while still showing off the shape of the shoe.

Your ankle boot styling options depend on the kind of heel you’re working with, so I’ve split my examples into 3 categories: wedges, flats, and heels.

Wedge ankle boots

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Wedge boots are my favorite so I put them first! You get extra height, which makes them easier to wear, but they’re still comfortable. I wear my wedge ankle boots with cuffed skinny jeans all the time. Skinny jeans make my short legs look as long as they’ll ever look (still not that long). But cuffing them a bit helps show off the shoe. If you have cropped skinny jeans, that would work too.

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Wedge ankle boots can work with a skirt or dress too, as long as the hem falls a few inches above the knee. The more leg that’s showing, the longer your legs look. Just keep it decent, OK ladies?

Shop Wedge Ankle Boots: Save // Spend // Splurge

Flat ankle boots

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Flat ankle boots are the hardest. They accentuate my lack of height, but I still love them! I wear them with cuffed skinny jeans just like my wedges. You’ll notice in both of the above outfits I tucked in my shirt – if you’re already cutting off the leg line at the bottom, you don’t want to do it at the top too!

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Friends don’t let friends wear leggings as pants. Always cover your junk. That said, leggings can be very slimming on your stems, and you can get away with a short tunic. Flat booties with leggings can be a fun alternative to sneakers or flip flops with a super casual outfit.

Shop Flat Ankle Boots: Save // Spend // Splurge

Heeled ankle boots

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Heeled ankle boots can be worn almost any way you would wear regular old pumps. They’re a great option for the winter because they’re a little sturdier than pumps and you get more coverage on your chilly feet.

Shop Heeled Ankle Boots: Save // Spend // Splurge

See more How to Wear posts:

Army Jacket     Oxford Shirt     Denim Jacket     Flared Skirt