Skip to content
Beautiful Shoes For Creative Women
FREE Shipping on all orders $249 and Over
"I Only Wear Flats"

Tomorrow Square Toe Chelsea Boot | Black

Tomorrow Square Toe Chelsea Boot | Black

Regular price $369
Sale price $369 Regular price

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

4.8
Rated 4.8 out of 5 stars
28 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
4.8
Rated 4.8 out of 5 stars
Based on 28 reviews
Total 5 star reviews: 25 Total 4 star reviews: 1 Total 3 star reviews: 1 Total 2 star reviews: 1 Total 1 star reviews: 0
Slide 1 selected
28 reviews
  • JT Profile picture for Jacqueline T.
    Jacqueline T.
    Verified Buyer
    I recommend this product
    Rated 5 out of 5 stars
    10 months ago
    AMAZING!

    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. Very happy customer.

  • HM
    Heather M.
    Verified Buyer
    I recommend this product
    Rated 5 out of 5 stars
    1 year ago
    Great boots

    I love the boots and great that included an extra pair of heels.

    They are very stylish and flattering. I have a wide foot and the square toe is surprisingly slimming as I was a little concerned it would make my feet look wider or clunky but not so.

    An extra pair of heels was included which is a nice touch.

    The boots are a little snug across the foot but no too much and feel confident they will give to be comfortable. They are nice and supportive around the ankle and arches.

  • DB
    Del B.
    Verified Buyer
    I recommend this product
    Rated 5 out of 5 stars
    6 days 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.

  • A
    Anon
    I do not recommend this product
    Rated 2 out of 5 stars
    2 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 .

    RY Profile picture for Radical Yes
    Radical Yes
    1 month 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

  • C
    catH
    Verified Reviewer
    Rated 3 out of 5 stars
    6 months ago
    Stylish and comfy... but

    Super - and dangerously - slippery on certain surfaces. Beware! Also, the shoe has come away from the sole after only a few months wear, which for the price is disappointing.

    RY Profile picture for Radical Yes
    Radical Yes
    5 months ago

    Hi Cat,

    Thank you so much for your honest review! I'm truly so sorry to hear that the upper has come away from the sole after only a few months of wear. This is not the quality we expect of our products, nor is it the experience we want our beautiful customers to have, so we are truly grateful that you have brought this to our attention.

    If possible, it would be amazing if you could kindly send through some photos of the fault you have experienced. From here, we can offer a solution! It is also amazing to have some photos so we can show our makers.

    Thank you so much for your feedback regarding the slippery outsole as well. Our newest version of the Tomorrow Boot, and other styles that share the same outsole, now have a rubber sole that is much more slip-resistant, which we changed immediately as a direct response to the feedback we received from our initial production. It has been a learning process that we are truly grateful to have caught onto and rectified.

    Looking forward to hearing from you! Please let me know if you have any questions.

    Warmly,
    Team Rad x

Frequently Asked Questions

Do the Tomorrow Chelsea Boots run true to size?
Yes, the Tomorrow Boot runs true to size. The sculptural, square-toed silhouette provides a generous toe box, making them an incredibly comfortable and great option for wide feet.
Are these boots comfortable for walking?
Absolutely. They feature an inbuilt memory foam cushioned insole for ultimate comfort, and are grounded on a stacked EVA rubber outsole that is both incredibly lightweight and flexible. These boots do not come with removable insoles.
Are the Tomorrow Chelsea Boots easy to pull on?
Yes! The boots are designed for easy pull-on comfort, featuring deep elasticised side gussets and a durable grosgrain pull tab at the heel, allowing you to slip them on and off with ease.
What materials are the Tomorrow Boots made from?
The upper is crafted from black leather with a polished sheen. Inside, they are completely lined in our buttery soft, signature electric peach sheep leather.
What is the design on the edge of the sole?
The Tomorrow Boot features a thoroughly modern, exaggerated exposed rand (where the sole edge extends away from the upper). As a playful detail, we've embossed a radical wink into the rear of the rand!
How do I care for my leather boots?
Regular waterproofing is essential to protect the leather from unexpected winter showers and cleaning them with a leather conditioner to polish out any scratches.
What is your return policy if the shoes don't fit?
You can return any full-priced order for an exchange, credit note, or refund within 30 days of receiving it through our Returns Portal. We cover the cost of the shipping label when Checkout+ is selected during checkout.
Please note that if you purchase these during a promotional or sale period, they are only eligible for an exchange or credit note. Items marked as 'Final Sale' cannot be returned unless faulty.