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Black Tomboy Toes Downtown Dapper Semi-Formal Derby Oxford Shoe in Vegan Leather - Men's Dress Shoe for Women
Black Tomboy Toes Downtown Dapper Semi-Formal Derby Oxford Shoe in Vegan Leather - Men's Dress Shoe for Women
Alex Perry modeling the Tomboy Toes line of Downtown Dapper semi-formal shoes for women

The Downtown Dappers in Black

Size Chart | Don't see your size?

Colors available

Select Downtown Dappers In Blue

            • Vegan Leather 
            • Derby-Style Lacing
            • Brogue Accent
            • Burnished Toe
            • Regular ("B") Width
            • Extra Wide ("D") Width
The Downtown Dappers are a pair of shoes that are exactly what they say they are. Feel good and walk with a smug little spring in your step with a set of derby oxfords that look classy and don't break the bank. Made with vegan leather and smooth rubber roles, the Dappers are sleek with a slightly more pointed toe and speak of a subtle charm. Derby-style lacing is less formal than the classic oxford style, so you won't feel too strange if you wear these shoes every day. As a lower-cost option, they still look nice enough to wear to a special occasion like a wedding or a big job interview.

Our best-selling Downtown Dappers are the perfect introductory shoe for a handsomely stylish person who wants to start dipping their toes into the more masculine end of footwear but isn't ready to spend hundreds of dollars on shoes. They come in a striking steely blue, a handsome sandy brown, a classic jet black, an eye-catching sharkfin grey, and a warm, confident dark brown. With smooth rubber soles that will last longer than the high-formality leather soles of other oxfords, the Downtown Dapper line of formal shoes are a great first pair that will make you proud to step out into public.

Each pair of Downtown Dappers comes with a complementary tin of neutral shoe polish.

Customer Reviews

Based on 81 reviews
Ryan Goodell
Built to Last

I'm finally getting around to leaving a review for these shoes that I purchased ages ago. As a trans man, finding masculine dress shoes in my size is nearly impossible due to the sizes normally cutting off one size larger than my foot. I remember coming across Tomboy Toes on the internet and when I had a wedding coming up, I decided to pull the trigger. I honestly can't remember what year that was, but these shoes are still as shiny as the day they arrived at my door, and I've never had to use the shoe polish that came included in the box. They're extremely comfortable, even sustaining a 12-hour day of walking on Capitol Hill in June of 2022, and I love that they're made of vegan leather instead of animal leather. I have another wedding coming up in May and just placed an order for the light brown Downtown Dappers and I can't wait to look just as sharp in those as I do in these. My only complaint is that there's a thin strip of brown on the sole as part of the design, so I can't get away with wearing these in my dress uniform, since they're WAY nicer than what the Navy issued me in bootcamp!

Karla Avila
Absolutely amazing quality and outstanding customer service

I have a friend’s wedding today and another friend recommended this site for shoes. My order arrived within 2 days but unfortunately I had to size down.
The box came with the return label making the process such a breeze. I shipped them back and concerned about timing I reached out to see when my replacement was going to be sent and explaining the time crunch. The team sent me my replacement size without even processing the return that was on the way back. I cannot say enough good things about my experience. 10/10 will be shopping here exclusively for dress shoes

Stink bugs

Shoes are gorgeous, exactly what I wanted, however they arrived with 2 stink bugs in the toe of one of the shoes! Not a welcome surprise.

Hi Sarah,

This is certainly a first for us, we've never heard of anything like that happening to a customer before. We're so sorry that's been your experience! We recently went through a big move from a small warehouse operation to a larger one - perhaps the stowaways snuck in at some point in the flurry of reorganization during the transition period. We're so sorry, we'll have a customer service representative reach out to see how we can make it up to you.

All the best,
The Tomboy Toes Team

Pete Botjer
Exactly What I wanted

I had been looking for dress shoes for a while and couldn't find any that weren't overly feminized. I saw an ad for Tomboy Toes and thought why not, I'll check it out! As soon as I put them on I fell in love. They were comfortable and sleek. They were masculine without being too big or obnoxious. I wore them for eight hours and they were some of the most comfortable shoes I've worn. I will definitely be ordering more from Tomboy Toes


I wore these to my high school graduation ball yesterday and they were perfect with my suit! I got lots of compliments! Men’s shoe stores don’t stock shoes in my size, and especially not vegan leather ones (which were a must have, since I’m vegetarian).They arrived in the mail the day before the ball, so the ball was the first time I wore them. But despite this, they were totally comfortable! Some reviewers commented on them having a strong smell, but that was not the case for me, I did not notice any strong smell at all. Another reviewer also said he was embarrassed by the logo being on the bottom of the shoes, but my shoes did not have a logo (which I was happy about). There was just a general abstract grip pattern. I cannot think of a single issue with these shoes, they were perfect! Cannot recommend enough!