- Add a classic touch to any outfit with the Madewell® The Benning Chelsea Boot.
- MWL Cloudlift Lite padding.
- Man-made sole.
- Leather lining and upper.
- Pull tabs on back.
- Round toe silhouette.
- Stretch gores.
- Imported.
- Product measurements were taken using size 7, width M. Please note that measurements may vary by size.
- Measurements:
- Heel Height: 1 in
- Weight: 15.5 oz
- Circumference: 12 in
- Shaft: 5 1⁄4 in
Madewell The Benning Chelsea Boot | Boots
$122.20 Original price was: $122.20.$96.99Current price is: $96.99.
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| Color | Warm Cinnamon |
|---|---|
| size | 5, 5.5, 6 |
| width | M |
10 reviews for Madewell The Benning Chelsea Boot | Boots
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Rated 3.14 out of 5


















Anonymous –
These boots look great, but I never got them on my feet! The elastic does not stretch much. I wear a size 11, so my feet are long but not wide. Maybe if you have a smaller foot it would be possible, but with a big/long foot, it was impossible. I tried for several minutes before giving up.
Jean –
I could noht get my foot into them! So I don’t know about the size . They are very heavy.
Anonymous –
I’m a solid size 8 and bought these in an 8. Great looking boots but even though I have narrow feet, these shoes are crazy hard to get your feet in. Elastic on chelsea boots gets loose over time so I understand making them tight at first, but I think the issue is the back of the boot/heel is reinforced (it’s extra hard) so when you go to slide your foot in, it doesn’t give and your sock gets pulled so tight against your toes it’s uncomfortable. The only socks I could get to work were super super thin socks, dress socks were too thick and winter socks are completely out of the question. The length is correct for the size, so going up a size might fix the issue but then your shoes are too long. If you use a shoe horn it might alleviate the problem but that shouldn’t necessary for chelsea boots.
Also with the back being hard, when you walk, your achilles rubs against it and is a perfect storm for blisters.
Lastly, the sole on the heel would be better if it were softer. It makes the shoes a little clickity-clackity sounding, and I imagine these shoes would not be comfortable to wear for lots of walking as a softer sole would give a bit more cushion.
Sadly I would not recommend these.
Anonymous –
Other folks mentioned trouble getting the boot on. I found it required a little push, but I didn’t really have a problem. To me, they seemed well-made and comfortable.
Lisa –
These boots are classic and will serve me for a long time. Top notch craftsmanship, sturdy sole, soft leather that doesn’t scuff easily. They’re perfect for walking the dog or for running errands. I love that the shaft is small and tall even though that makes taking off a bit of a challenge. But there’s no ankle gap and that makes me happy. I do wish they had more of an almond toe rather than round but my toes have plenty of room this way! You’ll love them . I sized down from my normal 7.5 to a 7. Still plenty of room for thick socks.
Anonymous –
Too small, very tight, and quite heavy!
Anonymous –
Uncomfortable with no give
Anonymous –
These boots have a sleek style. Saturated color & great quality leather.
LH –
This is a very cute shoe with good elastic stretch. These are much narrower than most chelsea boots. If you have a even a little width in your foot, these won’t fit. These also felt really short in the toe once I did get it on.
Anonymous –
The fit was true to size. I wear a size 5 but purchased the 5.5 so I could wear thicker socks with them.