Pants + Boots for Fall/Winter…from Work to Weekend


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One of the exciting changes of season in the Midwest is that we get to change up our footwear.  It’s getting time to put the open-toed shoes away and bring on the boots.

Whether you are shopping online or shopping your closet, there are boots that belong at work and boots that are fine for the weekend.

In general….

  • …the flatter the heel, the more casual the boot.
  • …with untucked pants the most visible part of your boot will be the toe and the heel.  Shop accordingly.
  • …more bling, styling and/or heel does not automatically translate to more work appropriate.
  • …if the best quality about the boot is comfort, it probably does not belong at work.
  • …if your feet get cold during the day, invest in good, thin wool socks and leave the outdoor boots outside.

Following are ideas for how to pair pants and boots for the upcoming Fall and Winter seasons from casual to suited looks using boots found on  Zappos has a HUGE selection of shoes for the entire family and they offer free shipping both ways.  I have used them for several years and happily vouch for a happy customer experience.  And in case you are wondering, this is a 100% sponsor-free blog post :)



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When the trend (or trends) are wearing you, it is distracting and can leave the wrong impression.  Or when something doesn’t fit – like a pant that isn’t long enough for the height of your heels – it stands out and may cause people to question your judgement.

The same thing goes for boots that are ready to be retired.  If I am lucky and rotate my boots enough, I can usually get two years out of them before they start looking too tired to be at work.



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Knee-high boots are great if you can find a pair that fits well.  That said, when it comes to being tucked into pants, they belong in the extra casual category.  These outfits are great for weekend activities with friends, family or your special someone.



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Step your look up for work with a jacket for a top layer, paired with a dark denim and a stylish pair of boots.

  • This orange-toned boot pairs well with the orange tone in the shirt.  It is OK if it’s not a perfect match because the two colors are far enough apart.
  • A mean cowboy-inspired bootie is a great way to add snap to a printed button down and casual jacket.
  • A bright peep-toe bootie can add a fun splash of personality when paired with a printed top.  Make sure the toenails live up to the shoe!
  • A sleek peep-toe bootie paired with a slim jean is a pretty finish for a pretty outfit.



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For the days when a suit is not required, a dress pant and top layer are perfect when paired with a dressy boot.



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Just because you’re in a suited look does mean you have to wear a boring boot!  Footwear is a great way to add personal style to a more conservative outfit.

  • Dark colors of footwear can be a great neutral.  In this case, a wine-colored bootie is a perfect pairing to a neutral outfit.  Pair it with a touch of a wine color in a necklace or earring and you’re immediately pulled together.
  • This is another example of a dark color accenting an outfit.  A dark purple bootie goes great with grey and a small embellishment will peek out from under the pant.
  • If neutral is your thing, these shiny grey boots will look great paired with a long suit pant while making a style statement.
  • For the most conservative look choose a simple boot with a touch of style.  With the embellishments hidden under the pant, you’ll feel stylish without flashing it for everyone to see.

Are you in need of assistance with an accessories overhaul?  Fabuliss can help with in-person personal shopping!

{ Fabuliss helps women and men learn how to create and shop for outfits that align with their personal brand.  Color, fit, closets and shopping. or 612-554-4629 }


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