As of last night, it’s official — we can no longer get away with anything shorter than a mid-calf boot, until this massive amount of snow melts (then in that case all of our shoes will be ruined, regardless). Tall boots seem like a simple piece of footwear, right? There are a ton of options, they’re practical, they’re [sometimes] stylish…but I haven’t always found them to be an easy thing to shop for.
I seem to have this love / hate relationship with tall boots…but mostly hate. In the category of things you MUST have, I would say a boot whose height ranges from mid-calf to thigh high (and anywhere in between) would be on that list. Up to you on the specific height, the type of heel (or lack there of), fabric and color…but some sort of non-ankle boot I would say is a wardrobe essential, at least when you live somewhere cold. For those of us who don’t have “perfect boot legs” (so I would say most people, including myself), finding these types of boots can be tough.
Every fall / winter season, I stalk every e-commerce site, find myself in department stores (which I really don’t like to do in person, unless it’s Barneys or Bergdorfs…and never on the weekends) and I either have to settle for a tall boot I sort of like or I just give up. I ended up finding some Isabel Marant knee-high wedge boots a year or two ago. Never wore them. Eventually, grew to hate them. And over the summer, I sold them. It was a regrettable decision to buy them in the first place (this is why you should never settle!) but at least I learned something from it…never buy wedge boots again. This year, I found a pair of Zara over-the-knee boots that I’ve only worn once. I think I still like them but OTK boots are tough, as I only like to wear them with dresses or skirts (they’re not very flattering on me otherwise) and I rarely wear those things.
I’ve also been on the hunt for lined boots that are actually warm, but other than practical “all weather boots” this type is few and far between (but thankfully I did find a few that you can shop at the end of this post). Now when it comes to tall boots, you can go for the Uggs and the rain boots (which if you live in Chicago I’m sure you already have quite a collection in this footwear category)…but what about when you actually want to look stylish and not get your legs full of snow? This is where tall boots come in.
Like I mentioned about over-the-knee boots sometimes being unflattering, so are other types of tall boots. Although I have a few pairs, mid-calf boots don’t do wonders for legs. When a shoe ends at the largest part of your leg (so either mid-calf or mid-thigh), that’s where it cuts you off and suddenly that’s the focal point of your leg (at least that’s how I think of it). So when wearing boots like these, stick to either a super skinny pant or wear with a dress/skirt (which would probably need tights at this point in time). That way, there’s no extra bulk and you can minimize the potential “unflatteringness” (which I realize is not a word but at least I get my point across).
Now let’s get to heel height and color. Obviously black is the ideal choice. There are a few shades of grey (no pun intended) that work too. I really cannot get behind the flat tan/brown boot though. Why? Because it’s almost always styled with a Longchamp bag or a Louis Vuitton Speedy and an oversized Michael Kors watch…which teeters the line of being basic (okay, it’s basic). If you’re going with a flat boot, I would go with black and make sure there’s some substantial sole. When it’s too flat, it’s not only unflattering but can actually be quite uncomfortable. The best flat boots are the ones with a 1-2 inch square block heel. Not only does it up the comfort level but they can be worn for day and night and they look better on the leg.
When shopping for a taller boot with a heel, remember this — the higher the heel, the closer we get to…looking a bit hooker-ish (I tried to sugar-coat it but why bother?) Some people can pull off hooker-chic (for example, NOT Taylor Momsen) but unless you’re Kate Moss, I wouldn’t go higher than 3 1/2 inches (of course this depends on the platform, boot height, etc. but this is just a general rule of thumb). I always think a tall boot looks best with a thicker heel (stilettos + boots = Kardashian…and not like Kim’s new Givenchy look post-Kanye, more like Kim circa 2007). So that’s something to keep in mind when looking for the perfect tall boots.
All in all, I realize it seems like there’s a lot of rules when it comes to tall boots. But after struggling with these difficult pieces of footwear for years now, I think I finally figured it out. And why would I keep this valuable information all to myself? If you’re going to take anything away from this post when you find yourself shopping for boots, just remember 1) the heel height — the taller the boot the lower the heel should be and 2) the height of the boots themselves — you know what looks good on you so if you feel that mid-calf is unflattering, try a knee-high or a just-over-the-knee boot. As always, there’s exceptions to every rule but it’s good to go in with a game plan because the tall boot world can be quite overwhelming.
To make things a little easier, here’s some CCF-approved styles that you can wear in the current 19 inches of snow in the ground.
Okay so am I crazy or do you also find it difficult to shop for the perfect tall boots? Do you have any tips / tricks you use while shopping for this footwear category?
Image via Pinterest & WhoWhatWear
I second your struggle with boots. I am of the thick calf variety and would boot shop, cry…repeat. I finally found black boots at L.L. Bean that were acceptable and fit me perfectly.
May have to disagree with the brown boot opinion. Puma made a pretty awesome flat boot about 3 or 4 years ago and then discontinued them. Needless to say it will be a sad day when mine give out to wear and tear.
I am moving to Chicago in the summer so I think some fur lined boots will be in order soon thereafter. Any suggestions would be appreciated.