Dress Shoe Fashion Tips: Matching Socks, Accessorizing with Colored Laces, and More!

We're back with another awesome interview blog post, this time featuring the fashion wisdom of Stephanie Ash-Perry, the stylist for the official Tomboy Toes photoshoot earlier this year. For those of us who are just getting into the world of dressing to kill, she's got some answers to our burning questions about how best to wear and pair these formal vegan leather dress shoes. Let's dive into it!


Do I have to pair masculine dress shoes with a suit? Could I wear oxfords with a dress or skirt?

Absolutely! A cute pencil or a-line skirt goes a long way - try to keep the hem around the knee because it makes your leg look longer and will be more of a flattering combination with the shoes. If you go for a waist high skirt that will make you look especially long and elegant.


If you're going to wear a skirt with dress shoes should you wear short socks or tall socks or does it matter?

I personally am not a big fan of long socks with skirts unless they're tights, but a cute pair of a little over the ankle socks in a cool pattern works well.


Could I wear my Tomboy Toes shoes with tights?

Yeah totally! Especially if they’re tights with a cute pattern or patterned nylons.


The Roguish Brogues in Light Brown

What kind of socks are you supposed to wear with brown dress shoes and blue dress shoes?

With blue shoes I lean towards grey, navy, white, or black, but a pop of complimentary colour like a blue-purple works. With the blue Downtown Dappers, a pale blue can be a really nice touch.

When it comes to brown dress shoes, especially with this brand, I really like warm oranges, browns, and whites. Green is also REALLY CUTE with the dark brown Dappers, specifically either a spring green or a really deep forest green.


Are there sock colors you're absolutely not supposed to wear with brown shoes or blue shoes?

With brown dress shoes, I’d very strongly recommend against grey and brown unless it's a really warm grey, almost beige, and black is kind of a no-no because it's too dark, just like with navy. Brown is a tricky neutral.

As far as picking socks to wear with blue dress shoes, unless you're really brave I would suggest avoiding yellow and orange because that is the Starkest Contrast Ever and very dramatic. You have to do something like that deliberately and plan the rest of your outfit around it – it’s not easy to make that work, but if you feel up to the challenge, kudos to you!


What's your opinion of trying to make coloured shoelaces work with a more formal outfit – are colorful laces like green or red or purple suited to a formal setting like a wedding or dinner or office environment?

This is a situation where it will depend entirely on the culture of your workplace. Some offices will object to any non-traditional fashion decisions, and others will gleefully embrace little flourishes as long as they’re tastefully done. If you’re not sure, ask!

If you’re in a situation where having a bit of green or purple in your outfit isn’t considered unprofessional, feel free to match the color of your laces to the color of your shirt, your tie, your bag, or even your lipstick. Orange laces and a coral bag would be super cute.

Accessories are key to balancing an outfit if you're going to throw a splash of color at it. For something like a wedding, you could liven up a black suit with black shoes and purple laces and matching a purple pocket square and tie.


Last question! What would you say is the #1 fashion faux pas when it comes to formal dress shoes?

Oh man! I don't particularly think there is one. That said, I’m so against wearing brown with black. Don't wear brown with black, just don't do it.

Other than that, my number one rule is don't shy away from wearing something if it makes you feel good to wear it! Confidence is key!

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