10 affordable vintage style winter shoes under $50
image source: The Vintage Workshop

Today I want to share some affordable vintage style winter shoes. I have such a hard time with shoes in the winter. Most of mine are sandals or peep toes. I'm also afraid to wear vintage originals in the winter because the wet, chemical-coated ground can't be good for an ancient shoe.

 My most loved pair of shoes for comfort and simplicity are my black t strap pumps from Angel Steps. I can wear them all day without discomfort and although they were $25, they have held up to near daily wear since I bought them last year.

My best friend and I are always on the lookout for great "old lady shoes" because they are built for comfort and styled to look like the shoes they had when they were young women.  These shoes come in sizes 6-11 in wide, narrow and regular width so you're sure to get a perfect fit. If you order the wrong size, exchanges are easy and quick.  Here's my pick of 10 vintage style shoes that won't freeze your toes or your bank account.

Angel Steps Sybil Pump
A stunning low-heel, closed toe t-strap pump and can you believe it- a very similar pair of original 30's shoes sold at Adeline's Attic on Etsy. This modern pump has cut-outs on the vamp, just like the original, with hidden stretch at the buckle for fit and comfort. In black, burgundy, navy and light grey.
Modern Version $30

10 affordable vintage style winter shoes under $50



Angel Steps Casey Shoe
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Any smart 40's college girl knew that every girl needs a basic slip-on. I wear them with skirts, trousers, suits, dresses- you name it! On days when I wear a pair of killer heels, I usually toss some comfy slip-ons in a tote bag in my car so I can switch out if I need to.  Available in black, brown and navy
Modern Version $20

10 affordable vintage style winter shoes under $50






 Angel Steps Eva
I just spotted this brown leather pump as  I was writing this post and it's not on my Christmas list! A lovely low heel, t-strap and pleated toe- very much like these originals (circa 1927-1933 from vintage textile.com) Aren't they beautiful in navy?
Modern Version $30

10 affordable vintage style winter shoes under $50






Natalie Bootie
Imagine how cute these could be with a little bow, tassle, faux laces or shoe clip added to the front. Heeled ankle boots are popular in today's fall and winter wear but these these booties have a lower heel than most. This boot comes in tan,. brown, black and burgundy. I'd love to get one of each and use the vintage originals for embellishment inspiration.
Modern Version  $10

10 affordable vintage style winter shoes under $50




 Lucy from Comfort Well
The cut outs on this classic shoe remind me of snow flakes and who says you can't wear white shoes after labor day? Pair these with a red wool skirt for your holiday party or a day at the office.
Modern Version $3.99
10 affordable vintage style winter shoes under $50
original shoe (left) from Jamric Vintage on Etsy



1930's white perforated shoes from airstream apparel



Drizzle Boot
A practical styling of the original 50's over-shoe galoshes, this modern "drizzle" boot doesn't have a heel so you can wear them with your daily ballet flats and other smart rainy day shoes.
Modern Version  $10

10 affordable vintage style winter shoes under $50


Tinker boot
As much as I love the vintage Gaytees boots with the high heel and fur trim, I prefer a low heel or flat boot to brave those icy streets. This lower heel boot is very reminiscent of the 1940's "military boots".
Modern Version $25








Sofwear Melanie
This modern shoe is so 1930's. I was so excited to find its vintage match at The Delightful Dressmaker on Etsy The modern version comes in black and regular leopard prints- not as authentic but still fun!
Modern Version $30









Norwegian slipper


 Get cozy with a cute Norwegian slipper, lined in fleece. They remind me of hand knit vintage socks or these 1950's Ripons slippers
Modern Version $10





Faux fur trimmed short boots
When the snow is 2 feet deep and the parking lot at the grocery store is full, a girl has to get practical. These original "Eskiloos" are from 1959- with a faux fur collar and sturdy tread, they are perfect for snow ball fights!
Modern Version $35




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