I love wearing dresses year round. But wearing dresses in the fall can be chilly and a little tricker to wear. These tips will help you wear your fall dresses well!

SIMILAR GRAY CARDIGAN | SIMILAR LEOPARD DRESS | BLACK ANKLE BOOTS 

SIMILAR CABLE KNIT SWEATER | SIMILAR TAN FLATS

Why the “before” dresses in the fall outfit needs improvements:

  • There are plenty of layer options you can do over dresses in the fall, including cardigans! But this gray cardigan isn’t a great choice with a midi dress. I’m just so covered up with this outfit that I have no shape!
  • Also ankle boots can absolutely work with dresses too, but a heavy black boot does not work for this kind of outfit. It feels clunky and heavy with a flowy dress.

A few easy ways to improve your pullover sweater outfits

  • You can do a denim jacket or a suede or leather jacket over the top of dresses in the fall, but a sweater is a soft and cozy option. But instead of a cardigan, try a pullover sweater!
  • Take a hair tie and create a “ponytail” with the sweater and then tuck it up and under. This makes the sweater shorter and defines my waist so it’s super flattering.
  • I swapped out the ankle boot and did a tan flat instead so I elongated my leg line (it’s that kind of “barefoot” look when the shoe matches your skin tone).

If you’re more of a visual person, here’s the same advice in action

Looking to add a few dresses for fall to your closet this season?

I’ve linked a few fall dresses below!

Other outfits with dresses in the fall to give you some inspiration

Why these outfits work:

  • Outfit 1
    • My natural waist is defined with a waist tie. Super flattering!
    • The scarf adds some pattern and interest to a solid colored dress
    • Tan shoes elongate my leg and don’t feel heavy or add weight to the bottom of my outfit.
  • Outfit 2
    • It can be tricky to pair a long dress with a long cardigan, but with a belt to define my waist, and a hat to draw attention up to my face, and a pair of tan ankle boots to avoid adding weight to the bottom of your outfit, IT WORKS.

Why these outfits work:

  • Outfit 3
    • This is a boxy dress that could easily give me no shape. But the jacket helps give some structure to my upper half, and the knot on the hem of the dress keeps the hemline from getting too long and overwhelming.
    • Pointed flats help elongate my leg line
    • Long curly hair creates a bit of a statement and draws attention up to my face!
  • Outfit 4
    • My waist is defined underneath my jacket
    • The length of the jacket is cropped, which keeps my proportions good (so my waist doesn’t look disproportionately high)
    • Tan ankle boots elongate my leg line

Think you can wear your dresses in the fall now? Go for it!

See the rest of the 2020 Fall Style Guide HERE!

The Fall Style Guide: Dresses in the Fall

I love wearing dresses year round. But wearing dresses in the fall can be chilly and a little tricker to wear. These tips will help you wear your fall dresses well!

fall dress outfit

SIMILAR GRAY CARDIGAN | SIMILAR LEOPARD DRESS | BLACK ANKLE BOOTS 

SIMILAR CABLE KNIT SWEATER | SIMILAR TAN FLATS

 

Why the “before” dresses in the fall outfit needs improvements:

  • There are plenty of layer options you can do over dresses in the fall, including cardigans! But this gray cardigan isn’t a great choice with a midi dress. I’m just so covered up with this outfit that I have no shape!
  • Also ankle boots can absolutely work with dresses too, but a heavy black boot does not work for this kind of outfit. It feels clunky and heavy with a flowy dress.

A few easy ways to improve your pullover sweater outfits

  • You can do a denim jacket or a suede or leather jacket over the top of dresses in the fall, but a sweater is a soft and cozy option. But instead of a cardigan, try a pullover sweater!
  • Take a hair tie and create a “ponytail” with the sweater and then tuck it up and under. This makes the sweater shorter and defines my waist so it’s super flattering.
  • I swapped out the ankle boot and did a tan flat instead so I elongated my leg line (it’s that kind of “barefoot” look when the shoe matches your skin tone).

 

If you’re more of a visual person, here’s the same advice in action

fall dress outfit

Looking to add a few dresses for fall to your closet this season?

I’ve linked a few fall dresses below!

 

 

Other outfits with dresses in the fall to give you some inspiration

dress for fall
fall maxi dress outfit

Why these outfits work:

  • Outfit 1
    • My natural waist is defined with a waist tie. Super flattering!
    • The scarf adds some pattern and interest to a solid colored dress
    • Tan shoes elongate my leg and don’t feel heavy or add weight to the bottom of my outfit.

 

  • Outfit 2
    • It can be tricky to pair a long dress with a long cardigan, but with a belt to define my waist, and a hat to draw attention up to my face, and a pair of tan ankle boots to avoid adding weight to the bottom of your outfit, IT WORKS.

 

fall dress with jacket
fall dress outfit

Why these outfits work:

  • Outfit 3
    • This is a boxy dress that could easily give me no shape. But the jacket helps give some structure to my upper half, and the knot on the hem of the dress keeps the hemline from getting too long and overwhelming.
    • Pointed flats help elongate my leg line
    • Long curly hair creates a bit of a statement and draws attention up to my face!

 

  • Outfit 4
    • My waist is defined underneath my jacket
    • The length of the jacket is cropped, which keeps my proportions good (so my waist doesn’t look disproportionately high)
    • Tan ankle boots elongate my leg lin

 

Think you can wear your dresses in the fall now? Go for it!

See the rest of the 2020 Fall Style Guide HERE!

If you want to save the Fall Style Guide, enter your email below to get your digital download of the complete Fall Style Guide!


One Comment

  1. Erica says:

    What about leggings? if tall boots are out, what shoes do you wear with them? Or are leggings out, too?

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