How To Wear Thigh-High Boots To Work And Not Get In Trouble

There are a few simple suggestions I like to follow when pushing dress code limits.
Publish date:
November 26, 2013
boots, dress codes

Read more from Kelly at xoVain!

I currently spend half of my week doing freelance writing from home and the other half working at a college library. When I’m working at home, my hardest outfit decisions are along the lines of, hm, do I order the Totoro snuggie or the unicorn snuggie?

At the library, however, I have to follow a dress code. Our dress code forbids t-shirts, open-toe shoes, and jeans -- but it doesn’t say anything about stripper boots. They probably thought it didn’t need to. But then they hired me.

I love to have fun with makeup and fashion, and there’s nothing I like more than a wardrobe item that pushes me past my boundaries. Sometimes I get weird looks and feel uncomfortable and regret it, never to wear that faux green fur coat from Zara again.

Other times, well, I still get weird looks but just ignore them because whatever I’m wearing makes me feel awesome. These boots fall into the latter category. They’re faux leather thigh-high boots with an almost four inch heel, and I often wear them to work.

My boss hasn’t said anything, probably because 1. She’s the nicest lady in the world and 2. Like everyone else, she’s used to my random style experiments. Much like Lady Gaga, I seem to have gone too far and crossed the line into predictability.

Still, it probably helps that I’m always very careful to style these boots appropriately for work. Here are my --well, not rules -- but suggestions for successfully getting away with wearing thigh high boots to work, along with five examples of how I style them.

Minimize Cleavage

This is admittedly an easy one for me since I don’t really have any to hide in the first place. Still, you know the old rule about picking legs or boobs but not both? Since these boots draw so much attention to the legs, it’s best to pick a top or dress with a high neckline.

I also try to have the hem of the dress at least skim the tops of the boots. If you want to pair a midi dress or skirt with them, even better (I avoid those like the plague because I’m tiny).

Avoid short sleeves

Obviously these boots are for fall and winter; I can’t imagine wearing them to work in July. So it should be pretty easy to pair them with long sleeves. Covered-up equals conservative in my mind, so that’s my main strategy for balancing out the va-va-voom vibe of these boots. That doesn’t mean you have to look boring, though. Utilize layers for visual interest!

In this case, I paired a tiny, short-sleeved plaid dress from Forever 21 with a boy’s blazer that I thrifted. Blazers always make you look more professional, no matter what you’re wearing. I would know -- I got away with yoga pants by using that trick once.

Prints and bright colors are your friends

In case you didn’t notice this trend already with the florals and plaid above, I’ve found that it’s best to stay away from all black when wearing these boots to work. Even paired with a conservative black turtleneck dress, the boots felt too BDSM for the office in conjunction with all that black. Thus, bright colors!

Mustard and red is one of my favorite color combinations, and I included a little leopard print belt for fun. Notice that my skirt is long and structured but not too tight, and my sweater’s V-neck is too high for cleavage.

Avoid showing any leg skin

I think that little strip of thigh skin showing is so sexy, which is why I own thigh high boots and lots of thigh high socks. It’s also why I always cover my entire leg when wearing these boots to work. If you’re wearing a shorter skirt, as I am in this outfit, make sure to wear thick leggings or tights underneath.

And speaking of a short skirt, make sure it’s not body-hugging and in a thick fabric like wool. I found this one in a thrift store but it’s originally from J. Crew.

Wear them with PANTS--not leggings or tights as pants

It makes for a cool weekend look if you pair thigh high boots, leggings, and a giant sweater. It’s not cool to wear that to work; it just reads as way too casual. If you’re not into skirts and dresses, feel free to wear these boots with a sturdy, fitted pair of pants. I prefer a dark, muted color rather than black so they stand out against the boots.

Basically, just make sure you’re not showing too much skin or wearing entirely black leather and you should be good.

As for the boots themselves, if you’re looking for a pair and you think you’ll want to wear them to work, there’s a few things to avoid. Don’t get a pair that’s TOO shiny, or that has corset-like lacing. You also want to avoid anything you can’t walk or sit in. Of course, the shorter and thicker the heel, the easier it will be to walk in. I am completely against wedges for thigh high boots though; sorry. And unless it’s suede, avoid anything that’s skin-tight.

Finally, here’s a few shopping options for thigh high boots (mine are included; they’re the ones from Forever 21 of course, SIGH).

Would you wear thigh-high boots to work? Do you think I’m crazy? OR did you go into this thinking that I’m crazy, but then you slowly got won over by my adorable and totally work-appropriate outfits?

Also, if there’s anything that you want to wear to work but aren’t sure how, share in the comments! I’d love to help.

Follow Kelly on Twitter @picturesqueliar for totally non-work appropriate tweets.