If you take your cues from fashion magazines, over-the-knee boots should be everywhere. They're on-trend, slightly edgy, flattering, and add a dose of sexiness to any outfit. But if you look around you, you'll see that most women (at least in San Francisco, which I know isn't saying much) are still clinging to the basic black ankle bootie. The black ankle bootie is to San Francisco in 2016 what a black North Face jacket was to any college campus in 2008. It's not unflattering or ugly--in fact, it's universally flattering and inoffensive. But after seeing it a gazillion times on myself and others, it can get a teensy bit boring. Shake things up with an OTK boot--and don't worry, there are many ways you can wear it, depending on how daring you are:
1.) Over skinny jeans
This is probably how most people will wind up wearing the OTK boot, because it's just the least scary option. That's not to say it's a boring option (are OTK boots ever boring?) but if you want to plunge into this trend without attracting too much attention, this could be a good way to dip your toes in the water. Dark-wash skinny jeans paired with flat, black OTK boots could even be appropriate for work, provided your workplace is casual. Higher-heel OTK boots over skinny jeans work for a night out, especially if paired with a crop top and a leather jacket.
2.) With a baggy dress
This outfit is statement-making, but not over the top--that's why the dress is baggy. An oversized but short sweaterdress or tunic looks awesome with over-the-knee boots because it balances one of the age-old fashion tricks: cover up one thing, and show off another thing. Eyes will gravitate to your super-sexy legs, because the bagginess of the dress will detract from all your other, um, assets. This outfit is obviously too much for work, but could be cute for daytime or nighttime on weekends.
3.) With a mini shift dress
This style is similar to the baggy dress style, but with a bit more structure. Shift dresses conceal the lines of the body, but aren't quite as drapy as loose tunics, so they add a bit more polish and elegance. If the boots are flat, this look could even be work-appropriate (again, depending on workplace) especially if paired with a blazer.
4.) With an A-line mini skirt and sweater
A-line skirts balance innocence and sexiness very well. The ones currently in style (usually denim or corduroy with buttons down the front) conjure up images of high school students in the late 1960s. To give these skirts a modern, more daring twist, pair them with OTK boots, making sure to keep your top half covered up with a high neckline sweater.
5.) With a fit and flare dress
Fit and flare dresses are perfect with OTK boots. This is a great transitional outfit between winter and spring, when you aren't sure if it's pants weather or dress weather. The fact that fit-and-flare dresses don't cling to the hips also means
6.) With a high-neck bodycon dress
This is probably one of the most daring options, and I wouldn't really recommend it for anything other than nightlife (that said, for many people nightlife outfits are a huge part of their wardrobe!) As long as the neckline is high, this getup can still be appropriate for very specific occasions, and it's the perfect outfit if you really want to make an entrance. If it's a bit too sexy for your taste, you can always dress it down with a looser jacket.
7.) With shorts
Woah, before you tell me this is too Pretty Woman for you to attempt, think again. Provided the shorts actually cover your butt cheeks, and provided you're not wearing a super-tight crop top showing boatloads of cleavage, this look can actually be really cute. For some extra coverage, add a looser open sweater or a flowy tee. If this look is still too risque for your taste, consider opting for flat-heeled taupe boots instead of high-heeled black ones.
1.) Over skinny jeans
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| Source |
This is probably how most people will wind up wearing the OTK boot, because it's just the least scary option. That's not to say it's a boring option (are OTK boots ever boring?) but if you want to plunge into this trend without attracting too much attention, this could be a good way to dip your toes in the water. Dark-wash skinny jeans paired with flat, black OTK boots could even be appropriate for work, provided your workplace is casual. Higher-heel OTK boots over skinny jeans work for a night out, especially if paired with a crop top and a leather jacket.
2.) With a baggy dress
![]() |
| Source |
This outfit is statement-making, but not over the top--that's why the dress is baggy. An oversized but short sweaterdress or tunic looks awesome with over-the-knee boots because it balances one of the age-old fashion tricks: cover up one thing, and show off another thing. Eyes will gravitate to your super-sexy legs, because the bagginess of the dress will detract from all your other, um, assets. This outfit is obviously too much for work, but could be cute for daytime or nighttime on weekends.
3.) With a mini shift dress
![]() |
| Source |
This style is similar to the baggy dress style, but with a bit more structure. Shift dresses conceal the lines of the body, but aren't quite as drapy as loose tunics, so they add a bit more polish and elegance. If the boots are flat, this look could even be work-appropriate (again, depending on workplace) especially if paired with a blazer.
4.) With an A-line mini skirt and sweater
![]() |
| Source |
A-line skirts balance innocence and sexiness very well. The ones currently in style (usually denim or corduroy with buttons down the front) conjure up images of high school students in the late 1960s. To give these skirts a modern, more daring twist, pair them with OTK boots, making sure to keep your top half covered up with a high neckline sweater.
5.) With a fit and flare dress
![]() |
| Source |
Fit and flare dresses are perfect with OTK boots. This is a great transitional outfit between winter and spring, when you aren't sure if it's pants weather or dress weather. The fact that fit-and-flare dresses don't cling to the hips also means
6.) With a high-neck bodycon dress
![]() |
| Source |
This is probably one of the most daring options, and I wouldn't really recommend it for anything other than nightlife (that said, for many people nightlife outfits are a huge part of their wardrobe!) As long as the neckline is high, this getup can still be appropriate for very specific occasions, and it's the perfect outfit if you really want to make an entrance. If it's a bit too sexy for your taste, you can always dress it down with a looser jacket.
7.) With shorts
![]() |
| Source |
Woah, before you tell me this is too Pretty Woman for you to attempt, think again. Provided the shorts actually cover your butt cheeks, and provided you're not wearing a super-tight crop top showing boatloads of cleavage, this look can actually be really cute. For some extra coverage, add a looser open sweater or a flowy tee. If this look is still too risque for your taste, consider opting for flat-heeled taupe boots instead of high-heeled black ones.





















































