In our latest column, "Ask a Fashionista," you can solicit our strongly held opinions on everything from how to wear a midi skirt without looking like a tree stump to whether a certain retail CEO should go ahead and resign already. Q: I own lots of pairs of high top sneakers but don't know how to style them to look flattering with jeans or skirts. — Allison, Chicago, ILThe high top conundrum is real. As a person who prefers the high top version of every shoe, from creepers to Nike Dunks, I've struggled with styling my kicks for decades – and I'm going to share everything I've learned. The first step to figuring out how to wear the tricky sneakers is identifying the type of high tops you want to wear. I break them into two categories: thin and thick. A thin high top is something like a pair of Chuck Taylor All Stars, a shoe that is made of a light fabric that, when tied to the top, rests snugly against the leg. An example of a thick version would be a Nike Air Force 1 that is wide at the ankle and has more bulk.

OK, let's start with the harder of the two: the thin high top. The issue with a thin high sneaker is that when laced all the way to the top tightly it can make one's ankles look awkward and small – especially when paired with skinny jeans or tights. nike shoes with lights on the bottomMy first trick is to never, ever lace the kicks to the top loop, and instead tie them in the middle loosely so that the sneaker tops aren't tight against the ankle. top 10 soccer shoes 2013The second trick is to wear pants with your high tops that are wide at the bottom or allow for a peek of skin to pop out between the pants and shoes – this will keep your body proportions feeling right.top 10 tennis shoes for flat feet

The picture of Kati Nescher above is a good reference for a casual look, while I also love this just rolling the bottoms of jeans to create volume to offset the sneakers. what running shoes should i buy for flat feetFor the most part, I'd say steer clear of dresses or skirts with thin high tops – it's maybe a little too Avril Lavigne at the prom? which running shoe is best for flat feet– but to each her own.white golf shoes with black pants Check out these high tops for some thin sneaker inspiration.youth golf shoes nike 5 Gallery And now for the thick high top ....80 off on nike shoes

When it comes to a chunky sneakers, you can go down one of two roads. The first is to pair it with bare legs and a miniskirt, like Ashley Madekwe did above. best price on new balance tennis shoesBecause the shoe has weight, it can stand on its own, and usually looks best without baggy pants or tights competing with it.cheap tennis shoes in los angeles The other option, illustrated below, is to pair a chunky sneaker with a skinny jean tucked into the sneaker. best running shoes for heavy weightIt's the pants equivalent of going bare-legged, leaving the kicks to stand alone as the accent of the lower half of your outfit.adidas and nike running shoes

Try it out with some of my favorite high tops in the gallery. 6 Gallery Homepage photo: Timur Emek/Getty Imagesbest cushioned mens dress shoesMost footwear was initially designed for use in athletics, with an eye on groundbreaking function, rather than how the sneakers look when worn on the street. running shoe brand for flat feetBasketball sneakers, in particular, have been some of the most difficult designs to wear with a pair of jeans, mainly because of the height of the sneakers.should i buy trail running shoes This often results in people wearing too-baggy jeans and having an overall sloppy aesthetic from the ankle down. ladies golf shoes south africa

That's not the only mistake people can make, though: There other tricks to successfully wearing sneakers made for on-court use in a casual setting. mens tennis shoes 2013To better outline them, here's  How to Wear Basketball Sneakers With Pants .best mens tennis shoes for walkingUser Reviewed How to Wear High Topscheap low top nike basketball shoes Two Parts: Deciding on High Tops Wearing High Tops Community Q&Atennis shoes on beach High tops have made a resurgence. tennis shoes for petsBest known as a trend from the 1980s, the high top sneaker has made a comeback with a wide variety of colors, styles, and brands - the shoe has even become upscale with labels like Isabel Marant, Viktor & Rolf, and Michael Kors designing their own high tops. places to buy trainers in the uk

High tops can be difficult to pull off because the shoe is so dominant. However, paired with the the right outfit, high tops can really put together a look and make you look unique, modern and fashion forward.puma sports shoes online shopping Think carefully about what style to get. puma shoes purchase onlineWhich type of sneaker do you want to wear: thin or thick? puma latest shoes priceA thin high top is something like a pair of Converse sneakers, shoes made of a light fabric that, when tied to the top, rests snugly against the leg. cheap puma shoes free shippingAn example of a thick version would be a Nike Air Force 1 or Reebok Freestyle that is wide at the ankle and has more bulk. puma shoes online shopping best price

The issue with thin high sneakers is that if tightly laced all the way up to the top, the shoes can make your ankles look awkward and small.puma sport shoes review With chunkier sneakers, be aware that they might make your feet appear larger than they are.runner world shoe test Think about what brand you like. best walking shoes cuteWhat have you purchased in the past? best walking shoes uk 2015What brand not only looks great but fits your feet? best hiking boots for ukOr do you want to go upscale and wear Raf Simons, Michael Kors, or Isabel Marant sneakers?best first pair walking shoes baby

The most important thing to remember when buying high tops is to ensure that they're a good fit. best name brand walking shoesThis does sound trivial but it’s easy to get the size and fit wrong, especially with online purchasing. best walking shoes in paris Think carefully about what color you want. good walking shoes for irelandConsider what would suit your personal style and also what you have in your wardrobe that complement them nicely. best shoes for fell walking Like many things, high tops are at their best in simplicity. walk over shoes style forum

Black is the best and safest bet for both men and women, like a pair of Reebok Classic Black Hightops. top ten table tennis shoesRemember that black basically goes with everything. best basketball shoe brands 2013The next best choice is white or another block color, like red, navy, etc.buy leopard print shoes online india Small injections of color can be fun; best boat shoes 2014 ukyou want what you wear to reflect your personality. best winter mountain bike shoes 2013But keep such injections of color small or limited to one color. best mens dress shoes under 250

If you’re thinking of going for a bright block color, the success of the look depends entirely on your surrounding outfit.best mens dress shoes for $100 If you are looking at the pair of sneakers that look like Skittles, pause for a minute. running shoes queen street melbourneYou might like the color, but you should also think about whether or not that color suits you, fits with your wardrobe, and is something you can and will wear for months. running shoes affiliate programNovelty colors are fun and can look great, but they can also get tiresome.running shoes birthday cake Wear skinny jeans with high tops. running shoes fargo

This is a great look and very contemporary - and it works for both men and women, since skinny jeans are popular for both! best running shoes for dodgy kneesBe smart in pairing your skinny jeans or other skinny pants or tights with sneakers. running shoes dress pantsFor example, if you're wearing black jeans, wear colored high tops. running shoes functionIf you're wearing colorful jeans, maybe go for a more subtle shoe choice.running shoes vs skate shoes As a general rule, don't wear converse the same color as your jeans (unless they're both black because black is a classic and basic shade). running shoes vs trail runners

This look really highlights the shoes and accents the lower half of your outfit.buy running shoes online south africa Wear pants with wider legs if pairing with thin high tops. top running shoes for a marathonDress your Converse or similar thin sneaker with pants that are wide at the bottom or allow for a peek of skin to pop out between the pants and shoes – this will keep your body proportions feeling right. best running shoes bostonThis outfit is a great option for most women! best running shoes for climbing For men, however, pairing baggy pants with high tops is a strict no-no. Wearing baggy paints with high tops creates a bulky look and makes men look clumsy and unkempt instead of cool and stylish. best running shoes high impact

Instead, men should pair their high tops with a pair of casual straight or skinny jeans, a cool T-shirt and an open cardigan (preferably the same color as the high tops). best running shoes for bad knees Roll the bottoms of jeans to create a bit of volume to offset the sneakers. best running shoes independentThis is a nice spring-and-summer look that works for both men and women, given the recent fashion trend of cropped pants. best foot shape running shoes Make sure not have any visible socks peeking out.best running shoes for very heavy runners Cropping or rolling your pants helps to focus attention on the shoe while purposefully showing a little ankle. youth running shoes sale

This look really only works with clean, smart sneakers of a single color. Dress up your sneakers. high top trail running shoesFor women, consider wearing dresses or skirts with high sneakers. running shoes to wear with skinny jeansThis is a great style for women that will highlight your legs and make them look long and lean.top 10 middle distance running shoes It's particularly ideal to wear clunkier shoes with skirts or dresses. best running shoes for pregnancyBecause the shoe has weight, it can stand on its own and usually looks best without baggy pants or tights competing with it.cheap nike womens running shoes uk

You may want to avoid dresses or skirts with thin high tops; sometimes this look can be a little dated. top nike womens running shoes 2014Think skater girls, such as Avril Lavigne, circa 2003.free running shoes nz Wear socks with your high topsmens running shoes without laces Men can also dress up their high tops though not perhaps with a skirt in most cases. best running shoe cross countryInstead, a well-fitted trench coat can look very chic and urban-modern with the right high tops. running shoe nike malaysiaTake care, however, to not end up looking like you're wearing a costume from the film "The Breakfast Club"! best running shoe poll

Pair shorts with high tops for a summer look.This is a key component of wearing high tops as a fashion statement. best running shoes in india under 2000You want to look cool, not like a slob who can't be bothered to tie his or her laces. running shoe store times square Show more unanswered questionsrunner's world best running shoes 2012 All these steps are just guidelines. where to buy cheap running shoes manilaYou don't have to follow them exactly. cheap clarks shoes online ukThe most important thing is that you make your own style and look unique.buy vans shoes in uk