Used loafers in Chicago typically sell for $20 to $94. Loafers are increasingly built to be resoled, and whether yours can be is most of what sets the price.
Selling loafers in Chicago
Chicago has real winters and generous pre-war apartments, which is an unusual combination and it shapes what sells. Serious cold-weather clothing has a genuine local market, and the older buildings mean full-size furniture actually fits, unlike in the coastal cities.
Leases across much of the city turn over on common dates, which concentrates moving into a few weeks and floods the market at once. That is the best time to buy and the worst time to be selling something ordinary.
The L covers the city well and is how most small items move. For furniture, the alley behind the building is usually the practical loading point, and winter is a genuine obstacle — nobody wants to carry a couch through snow, so prices soften.
Chicago, in Illinois, has around 2.7 million people, which means a deep enough buyer pool that most things sell without having to travel far to hand them over. Joliet, New York and Los Angeles are close enough that a buyer there may well make the trip for the right thing.
Handing it over in Chicago
Distances are the real constraint. State plainly whether you will ship or collection only, because a buyer three states away will otherwise ask.
What loafers are worth
What lifts the price
- Welted or stitched construction that can be resoled
- Original shoe trees, box and dust bags
What pulls it down
- Cracking across the flex point
- Stretched or collapsed backs
Working out what yours is worth
- Check the sole edge for a welt stitch line
- Flex the vamp looking for cracking
Getting it ready
- Look at the welt. A visible stitch line around the sole means the shoe can be resoled, and that is worth saying.
- Clean and polish the uppers, and check the heel for wear and the sole for thinning at the ball of the foot.
Photograph
- Both soles together, showing the welt stitching and wear
- The inside label with brand, size and any ‘made in’ marking
Put in the description
- Upper material and sole material
- Whether the shoe is welted and can be resoled
Post boxed with each shoe wrapped and shoe trees or paper inside to hold the shape. Light and easy to send, which widens your audience well beyond your own town.
Listing is free and there is no selling fee, so the whole amount the buyer pays stays with you. You and the buyer agree the handover between yourselves.
Same region (Illinois)
Common questions
Where can I sell loafers in Chicago?
Put it on WishThrift free and deal with the buyer direct. The L covers the city well and is how most small items move. For furniture, the alley behind the building is usually the practical loading point, and winter is a genuine obstacle — nobody wants to carry a couch through snow, so prices soften.
Are they leather soled?
Photograph the sole. Leather soles are a preference rather than an upgrade for some buyers, so state it and let the right buyer find you.
How much are loafers worth in Chicago?
Most used loafers change hands for $20 to $94. Condition and completeness move that figure more than anything else.
More: selling loafers across the United States, what loafers are worth, everything second hand in Chicago, or Shoes & Footwear in Chicago.
Guide range converted from sterling at the 2 August 2026 rate, not a quote — sellers set their own price.