Jeans Tucked Into Boots and You – A Cautionary Tale

Otherwise known as “You Look Like A Hooker In those Knee-High Boots.”

I’m sorry, but it’s true.


I went to the symphony last night, and for some silly reason I assume was aimed at making classical music more “accessible”, the performers and audience were invited to wear blue jeans. Yawn. Whatever. If I wanted to slum it in jeans on a Saturday night, I would have gone to the hockey game at the civic center half a mile down the road. As it stands, the area I live in is pathetically anemic in terms of even the least fancy of fancy dress events, so why I would want to trade in the opportunity to wear a cute, classy dress for yet another chance at throwing on crappy denim is beyond me. Also, it was insanely cold outside, making it my one and only opportunity this Florida winter season to bust out my huge, plush, Russian princess-style vintage faux fur coat and actually have it serve its purpose of keeping me crazy warm and appropriately formal. (As opposed to burning hot and inappropriately over-dressed.)

Needless to say, I was not wearing blue jeans. But a lot of people were, and here’s the thing: No matter how many hundreds of dollars you spend on an ultra fancy pair of denims, it’s difficult to make them look dressy beyond a certain point. The current way to attempt to get your jeans beyond the “looks alright for a classy restaurant/martini bar” phase and into the realm of “acceptable for an evening out at a fine arts event” is apparently to shove as much of them as you can into the tallest, stiletto-est pair of boots you can find. I learned last night that this is a bad idea. Allow me to demonstrate.

You thought you were going for this sort of look:

Classy – pretty riding jacket, the jeans fit well, the shirt is nicely tailored, and the boots complete an equestrian look.

Or maybe you’d try for this style, nicely exemplified by the lovely Sandra Bullock:

Biker jacket, biker boots, managing to make both look classier than either of their original iterations – job well done, Gracie Lou Freebush.

You’ve got knee high boots, you think, and a pair of absurdly expensive jeans. You can look like these pretty ladies! Nope, sorry, nine times out of ten you look more like Pretty Woman.

Or another well known whore:

How does someone with so much money manage to look like they stole the outfit off a mannequin at Wet Seal?

When 50+ women are doing this look on a German QVC “runway”, I think it’s safe to call it dead. (Also, the Germans have QVC? Who knew.)

Too sexy for your schnitzel.

Making this look work is prohibitively difficult. It requires the perfect storm of a bangin’ body, extremely well-fit jeans, and boots that are sexy without looking like they are literally selling sex. I’ve got more “bad example” pictures than “good example”, so here’s a few more to drive some additional nails in the coffin:


Oh, Raven-Simone. The things we’d talk about if we were friends. The boots? The jeans? The hat? The aggressive angel wing sleeves sprouting from your gaffer tape corset?


These boots were made for sluttin’?

I understand that in the last picture, the girls aren’t wearing shirts in any proper sense of the word, and that definitely gives them bonus points in the “Oh girl, no” category. Regardless, they appear to be doing some sort of low-rent Pussycat Doll choreographed routine in a pro wrestling ring, and if that isn’t enough to make you not want to emulate any aspect of their style, then I just don’t know what to tell you.

To avoid being overly curmudgeonly, I will acknowledge that I like the look of flat riding boots with skinny jeans – I think it’s because riding boots are generally wider at the top and do more to make legs look thin and long than their skin-tight hooker boot cousins. It goes well with a relaxed, slouchy look, as shown by Katie Holmes:

But keep in mind that she’s about 15 feet tall and has legs up to her ears.

I probably wouldn’t have noticed or cared enough to whine about boots in a blog post if it weren’t for the fact that “casual day” at the symphony provided a large assembly of women of all shapes and sizes doing variations on a theme. It isn’t often that you get such a broad sample set from which to gather data, but when a theater full of women all decide to dress up denim, it’s easy to see trends in action. There’s a ton of bloggers and varying other internet peoples talking up the boots-in-jeans look and going on about how it’s a great look for all shapes and sizes, but I am naysaying all over that general consensus.


Unless you are Patty the Daytime Hooker, of course. In that case, I applaud you for wearing pants at all.

Patty’s the one on the left, in case you aren’t watching My Name Is Earl as often as you should.

Images mostly from the appropriately titled and extremely topical I have a sneaking suspicion that it’s some foot/shoe sub-sub-culture fetish site, but it is regardless a thorough and completely work-safe compendium of images of people wearing jeans tucked into boots. Oh, internet.



Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )


Connecting to %s