A reader recently posted this call for advice on our Facebook page:
Alright style conscious little transguys: brands, websites, anything…I really need to look sharp for work this year. Totally fine getting clothes tailored, but cannot find nice dress shoes. I want some nice brown wingtips. Men’s 5 don’t seem to exist and all the boys styles have terrible round toes that look more like a work boot instead of a nice sleek shoe. I never in my life thought I would consider spending $250 on shoes (I freak out at $80), but that’s as high as I’ll go to finally have a sturdy, attractive pair of shoes I can love for several years.
I would start with dapperQ’s masculine dress shoe guide for smaller sized feet. It provides advice on styles, brands, and search engines for a wide range of dress shoes, from wingtips to monkstraps. But, since you’re looking for something very specific for this year, we’ve done some of the footwork (pun intended) for you and found some masculine wingtip styles that are available in “men’s” and “women’s” sizes now. (Note the quotes around “men’s” and “women’s” — if it suits your needs, no one needs to know what department some brand representatives arbitrarily assigned the shoe to.)
Men’s “UGG Allcott Collection” in Dark Brown/Naturale. Originally $350, on sale at 6pm for $140. Available in men’s size 5 – 11.5. Click here to purchase. Be sure to change the color selection in the drop down menu from charcoal to brown (if you prefer brown).
Women’s “BP ‘Harlan’ Slip-On Wingtip Oxford.” $79.95 at Nordstrom. Available in women’s sizes 5-11. Click here to purchase.
Women’s “Bedstu ‘Lita’ Wingtip.” $155 at Dillards. Available in women’s sizes 6-10. Click here to purchase.
BedStu Lita also available in this awesome color from TomboyX. Click here to purchase.
Women’s “Frey ‘James’ Wingtip.” Originally $218, on sale at 6pm for $130.80. Available in women’s sizes 5.5 – 11. Click here to purchase.
Women’s “Pikolinos ‘Brighton Tuxedo’ Oxford.” $170 at Amazon. Available in women’s sizes 5.5-10. Click here to purchase.
Style is very personal, so if these suggestions do not suit your tastes, visit our shoe guide for instructions on how to use fashion search engines to shop for alternatives.
I've been wanting these for a while, but they are currently out of stock in most sizes.http://tinyurl.com/pxsv7gv
I’ve been lusting after the Maisie Oxford and Millie Derby from Toast UK which are technically women’s shoes, but don’t have the cutesy look most women’s oxfords do. Also, made in England, so bonus for sane manufacturing conditions, one presumes.
I have had luck with Loake shoes’ ‘ladies brogues’. The gendered name aside, the shoes are masculine, providing a smaller cut of their men’s snoes. The soles are goodyear welted, so you can enhance the shoe’s bulkiness and height as well by getting a cobbler to add sole protectors.
http://www.loake.co.uk/loake-shoemakers/ladies/ladies-viv-brogue.html
A pair of Wanted Babe Brogues did the trick for me, but I really wish I had spent the money on a good pair and am looking to upgrade soon. A couple to consider:
Allen Edmonds McAllister (http://www.allenedmonds.com/aeonline/producti_SF6215_1_40000000001_-1_). You can special order your size or luckily snatch one on their factory seconds online store (shoebank.com). Check out the Strand model for a non-wingtip brogue.
SuitSupply Bordeuax Derby Brogue (http://us.suitsupply.com/en_US/shoes/bordeaux-derby-brogue/FW142125.html?start=8&cgid=Shoes)
For shoes especially, I believe it’s best to go for quality and a shoe that is Goodyear welted or has Blake stitching, so they can be resoled. If you take care of them, they can last for decades.
You may want to also try Poppy Barley. They offer made-to-measure mens shoes in sizes 5-15 and com in a variety of mens oxfords and leather boots. Find them here: https://poppybarley.com/shop/mens/
“J Shoes” makes some great wingtips in smaller sizes—and not much difference in styling between the “men’s” and “women’s” sections.
There’s also Nik Kacy, who makes gender neutral shoes from women’s 3.5 to men’s 14. Not a huge selection but it changes often. Usually, something’s on sale and the prices hover around $300.
https://www.nikkacy.com/collections