Skip to content
FREE Shipping on all orders $249 and Over
Green crossbody phone pouch with blue strap on a light gray background
Free Gift With Purchase
Free phone pouch worth $99 for the first 150 orders $299 and over. Add the pouch when prompted in the cart.
CALL ME

Tomorrow Square Toe Chelsea Boot | Black

Tomorrow Square Toe Chelsea Boot | Black

Regular price $369
Sale price $369 Regular price
or 4 payments of $92.25 with Afterpay

Meet Tomorrow! Our future classic sculptural chelsea boot made radical through her square toed silhouette

4.7
Rated 4.7 out of 5 stars
31 Reviews
  • alt-tag Black
×

Size Guide

Welcome back!
Based on your past purchases, we've already found your perfect fit for this style.
Method 1: Use a brand you own
OR
Method 2: Measure your feet
EUAU / USCM
365.5 / 622.9
376.5 / 723.5
387.5 / 824.2
398.5 / 924.8
409.5 / 1025.5
4110.5 / 1126.1
4211.5 / 1226.8
4312.527.5
How to measure foot in 3 steps

The imperfect world of shoe sizing.

We know how tricky online shoe shopping is, so don't despair if your new toe tappers are not your Cinderella-fit the first time around. We offer free shipping and free returns! Plus, we've collated all our Fitting Hacks to help you fit your shoes at home!

30 Day Returns
Secure Payment
Buy Now Pay Later with AfterPay or Zip Pay

"Love love love these boots they are everything I wished for and more. Super comfortable - think sneaker comfy! True to size and go with EVERYTHING. - Jacqueline T."

Fit & Sizing

Length
Short True to Fit Long
Width
Narrow Regular Wide
4.7
Rated 4.7 out of 5 stars
Based on 31 reviews
Total 5 star reviews: 26 Total 4 star reviews: 2 Total 3 star reviews: 1 Total 2 star reviews: 2 Total 1 star reviews: 0
Slide 1 selected
SizingRated 0.0 on a scale of minus 2 to 2
WidthRated 3.6 on a scale of 1 to 5
31 reviews
  • AS
    Angela S.
    Verified Buyer
    I recommend this product
    Rated 4 out of 5 stars
    5 days ago
    Stylish square toe

    These boots look great and are super versatile. They softened quickly across the toes and the leather is very nice. The only thing they’re missing is a bit more cushioning under foot so you might want to consider getting the radical yes shoe liner to go with them, for those long days of city strolling. Otherwise, love these boots!

    SizingRated 0.0 on a scale of minus 2 to 2
    WidthRated 3.0 on a scale of 1 to 5
  • ZP
    Zoi P.
    Verified Buyer
    I recommend this product
    Rated 5 out of 5 stars
    2 weeks ago
    Chelsea Black Boots

    Love them. True to size. So comfortable they’re perfect.

    SizingRated 0.0 on a scale of minus 2 to 2
    WidthRated 5.0 on a scale of 1 to 5
  • N
    Nicola
    Verified Buyer
    I do not recommend this product
    Rated 2 out of 5 stars
    1 month ago
    Beautiful boots but too slippery

    I love Radical Yes and have a number of boots, sandals and bags which I'm very happy with. These boots though are not great. Very slippery on heel and forefoot, worst on the heel. Great looking boots but I'm too scared to wear them after two bad falls. Same thing happened to my sister with her Tomorrow boots and she has also stopped wearing hers. They would need the heels and soles replaced to be wearable.

    SizingRated 0.0 on a scale of minus 2 to 2
    WidthRated 4.0 on a scale of 1 to 5
    RY Profile picture for Radical Yes
    Radical Yes
    2 days ago

    Hi Nicola!

    Thank you so much for sharing your honest feedback with us and for your kind words about our other shoes and bags that you have. I am truly sorry to hear that you’ve found the outsoles of your Tomorrow Boots to be slippery; that is the absolute last thing we want for our customers in our shoes!

    I wanted to let you know that we’ve actually updated our outsole production specifically because of feedback like yours. Since your pair was made, we’ve shifted to an outsole tread with much more grip, and the feedback has been that they feel significantly more secure now.

    To help with your current pair, a local cobbler can easily apply a "Topy" to the outsole, rather than replacing the outsole completely. For a bit of context, a Topy is a thin, durable rubber overlay that is bonded to the bottom of the shoe. It’s a fantastic way to instantly increase traction and also helps protect the original sole from wear and tear.

    If you’re interested, we would be more than happy to cover the cost of having this applied for you! Simply send through a photo of the receipt from your cobbler, and we will reimburse you immediately ❤

    We really appreciate you being part of the Radical Yes community and for taking the time to share your experience with us. If you have any other questions at all, please don't hesitate to reach out.

    Wishing you a lovely rest of your week!

    Warmly,
    Team Rad x

  • DB
    Del B.
    Verified Buyer
    I recommend this product
    Rated 5 out of 5 stars
    1 month ago
    Gorgeous Boots

    These boots are amazing. So comfortable from the first wear, absolutely no breaking them in whatsoever. Walked heaps in them, so so comfortable, and they are very cool looking as well. If you’re worried about spending the dollars, don’t be, they are the best boots ever.

    SizingRated 0.0 on a scale of minus 2 to 2
    WidthRated 3.0 on a scale of 1 to 5
  • A
    Anon
    I do not recommend this product
    Rated 2 out of 5 stars
    3 months ago
    Slip risk

    Bought last season. A great boot except for one important things. The soul has absolutely no grip and slips even on dry concrete and paths. Such a pity .

    SizingRated 0.0 on a scale of minus 2 to 2
    WidthRated 3.0 on a scale of 1 to 5
    RY Profile picture for Radical Yes
    Radical Yes
    3 months ago

    Hi Rad Friend! Thank you so much for taking the time to share your feedback with us. While we're happy to hear you love these boots otherwise, we’re genuinely sorry to hear they’ve been a slip risk for you.

    Since the production of these boots from last season, we have added more tread and a rubber layer to the sole in response to this. Your feedback is incredibly helpful as we’re currently looking into ways to incorporate even more grip into our dress soles for future productions. Because these styles feature a sleek, low-profile dress sole rather than a heavy tread, they can sometimes feel a bit smooth on certain surfaces.

    As a little "insider tip" to help you get more wear out of them now: we highly recommend asking a local cobbler to apply a layer of Topy (a thin, durable rubber overlay). It’s a very quick and affordable way to add instant traction and longevity to a dress sole without changing the look of the boot.

    Thank you again for sharing your thoughts, as we truly do value these insights. We absolutely love receiving feedback from our customers (the good and the bad) as it helps us stay true to our ethos of creating shoes made for real-world use. By sharing your experience, you are helping us refine and improve our designs to better serve our community, which is all we ever want to do!

    Warmly,
    Team Rad x