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Weekend Outfit Inspiration: Cognac Knee High Boots Two Ways

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Weekend Outfit Inspiration: Cognac Knee High Boots - The Well Dressed Life

On Monday we featured these boots on The Ten List. Pretty much everyone went crazy for them, with good reason. They are stunning. I can’t tell you how many times I’ve looked for a pair of boots just like these,  and found the perfect pair only to discover they were well over $500, or were reasonably priced but had some kind of deal-breaking logo/hardware on them.

These boots, by Kenneth Cole classic and ideal for this time of year.  They’re have some height to them, but the block heel makes them wearable.  I love anything in cognac, but if you need a black or dark brown boot, they are available in those colors too.

Today, we’re showing you how to easily wear these boots two different ways.

Thanksgiving Dinner

Weekend Outfit Inspiration: Cognac Knee High BootsDress, $120  |  Tights, $15  |  Clutch, $144  |  Belt, $40  |  Earrings, $23  |  Boots, $199

What else is there to wear on Thanksgiving other than a sweater dress?  They’re comfy, cozy and let you eat all the pie.  This mock turtleneck style, by J. Crew, is slightly body conscious. 

It comes with a self tie, which I replaced with a $40 double ring belt by Express.  Adding a new belt elevates the outfit. You don’t have to wear a belt at all if you don’t want to.  Then, I added these circle hoop earrings by Rebecca Minkoff to play off the hardware on the belt.

Last week, we featured a different sweater dress that is similar but less fitted that many of you picked up.  If you bought that dress, you can easily use it in this look.

For tights, I like Hue Opaque Tights. They are soft and warm, but not too heavy so you can move in them and slip your boots on and off without a lot of drama.  Need a clutch? I found this leather cognac bag at Brooks Brothers.  (On a side note,  I had no idea Zac Posen was working as Brooks Brothers Creative Director, but I’m down with it. I’m very, very down with it.)

Shop this Look


Thanksgiving Weekend

Weekend Outfit Inspiration: Cognac Knee High BootsJeans, $189  |  Sweater, $150  |  Bag, $25  |  Scarf, $20  |  Boots, On Sale, $170

Traveling to family? Visiting friends? Shopping?  Chances are you’re doing something festive over the weekend after Thanksgiving. Get double wear out of your boots by pairing them with a pair of skinny jeans and an autumnal sweater. You know why I love this look? Because the elements are as basic as they come, yet it’s so polished and pulled together.

My go-to, “better” skinny jean will forever be Paige. You just can’t beat the fit and ink blue wash.  If you are wearing a knee high boot with jeans, you have to wear a skinny, other styles won’t translate.  Don’t want to spend? You don’t have to, the Old Navy Rockstar jeans we’ve featured dozens of times, work well too.

Next, a cashmere sweater. I’ve mentioned C by Bloomingdale’s , their in-house cashmere brand,before. It’s well priced for the quality with classic styling.  This sweater is boxy so keep that in mind if you do order it. The rusty red screams fall. I found this plaid blanket scarf, that adds just the right balance of color, plus the weight of the scarf works with the weight of the sweater.

Finally, a $25 crossbody, in the same color as the boots is all you need for a day out with friends.

Shop this Look





Weekend Outfit Inspiration: Cognac Knee High Boots Two Ways

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Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.

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Mrs Jackie Rowley

Sunday 27th of January 2019

Thanks Megan for your weekend ideas I can put these into a seperate place so that I always have outfits that don't date and don't get worn out , How clever are you!!! Lots more like this please . Hope you and baby are well.

Best regards Jackie

Megan Kristel

Sunday 27th of January 2019

Thanks for the kind words, Jackie.

Molly M.

Sunday 28th of October 2018

Love these looks! I would love to see outwear that you would pair with outfits now that we are moving into the cold months.


Friday 26th of October 2018

I am a Parisian and I would like to congratulate you for your blog. It is both stylish and intelligent. thanks for the advice and the sense of classic style Marie-Gaëlle Gregory

Samantha Quaderer

Friday 26th of October 2018

Good morning! I love this post so much. I can only imagine the work that goes into creating all posts in general but especially the ones with multiple outfits so thank you. Boots are ordered. Can't wait to try out these outfits!

Megan Kristel

Wednesday 31st of October 2018

Thanks Sam!! Let me know how you like them!