The Tomboy’s Guide to Wearing Masculine Shoes with Skirts and Dresses

Anybody who says you can’t be femme and wear masculine dress shoes is clearly just lacking in imagination! The combination of a skirt or dress with some handsome chunky brogues or sleek dapper derbies is ideal for pulling off everything from the rough and tumble heartbreaker look to the always-approachable geek chic.

Darker men’s dress shoes like black and dark brown are ideal for the transition from your summer wardrobe to your fall wardrobe, when maybe you don’t want your toes exposed to the cold but you still want to feel like you’re made of magic when you twirl. Don’t let conventional wisdom tell you that these dashing shoes aren’t for you – you are the master of your own style, and we’re here to help you reach the next level in tomboy-femme fusion.

Pairing Skirts, Dresses, and Oxfords for Formal Situations

For formal wear, matching your dapper shoes to your outfit follows the same basic rules as pairing suits and shoes.

1. Don’t wear a black dress or skirt with brown shoes, or vice versa
2. Don’t wear white socks or stockings with masculine dress shoes, no matter the color
3. Unite the color of your shoes with a matching accessory somewhere in your outfit

In professional settings, you’ll be wearing skirts and dresses that are generally black, navy blue, or grey – with lighter tones like tan and white during spring and summer. As a basic guideline, here are the ideal shoes for each of those wear-to-work dresses and skirts:

Black oxfords or brogues, with dark stockings and accents in silver

Dark brown or black shoes, with navy blue stockings and accents in subtle brass

Dark brown or black shoes, with dark stockings and accents in black and white

Light brown, dark brown, or black shoes, with black stockings, and accents to match the shoes. Light brown is the least formal, black is the most formal, and dark brown is in the middle.

Dark brown oxfords or brogues, with tan stockings, and accents in dark brown

Light brown oxfords or brogues, with no socks, and accents in matching light brown

Some Key Tomboy-Femme Looks for Formal Occasions

Combine some nice oxfords in a dark brown or black with a calf length, collared dress. A white collar on a darker dress makes for a classic look that pairs well with the mature energy of a pair of nice masculine dress shoes, especially when you match a rich forest green dress to some coffee brown derbies. The added touch of some subtle earth-tone earrings and a skinny belt gives this look a very sophisticated feel, without going too Downton Abbey on your unsuspecting coworkers.

There’s a reason that the pencil skirt, blouse and blazer combination has been around for so long and always feels modern. Add a streamlined pair of masculine dress shoes – you probably want to avoid the busy brogue-patterned styles for this look – and you ever so slightly change the tone of this clothing combo to something with a bolder, more unique silhouette. The advantage of this three-piece outfit is that you can match the shoes to any one of the three items, as long as you follow the basic rules of combining colors.

Another great look to have in your tool box is the clean one-color shift dress with a matching belt and subtle stockings. Avoid loud, crowded patterns for formal situations and just stick to something solid, like a navy, maroon, or taupe, and use the rules for how to match your belt to your shoes. The uncomplicated, pure palette of this look allows you to be just a bit more funky with your foot choices and get away with brogues, and having some grey stockings to lead the eye from the dress to the shoes softens the gap between the two. You can break up the solid color of the upper dress with a long, dangly necklace in a simple gold or silver. Because this look is already quite strong and square, it pairs extremely well with masculine dress shoes.

Finally, step into the social limelight by pairing some bold brogues or derbies with a sleek pencil skirt and a fine-knit sweater and create a monochrome ensemble. What you’re going for is a very clean cut look – remember, this is still for a formal situation – so select a sweater that holds its own in terms of having the right sharp angles of professionalism to it. For jewelry, you can sway that balance a touch more towards the feminine with a few skinny bangles.

Pairing Skirts, Dresses, and Oxfords for Casual Situations

Once you hit the casual scene, the rules get a lot more loosey-goosey and you, fine tomboy, are freed to wear all sorts of combinations. You can also rock less common colours of masculine dress shoes, like blue, grey, or red – and don’t forget the fun shoelaces to add that extra special something.

Bright and Cheerful Tomboy-Femme Looks

As a rule, there’s something just so freeing about a brightly colored sun dress. Rock your favorite sun dress with any color of brogue or derby by adding some shoelaces that match the color of your dress and then, to really make the whole ensemble pop with obnoxious happiness, put on socks that are a contrasting color. We’re talking along the lines of blue dress, black shoes, blue shoelaces, and then red and purple striped socks. Or picture an orange dress, blue shoes, orange laces, and red socks!

If you’re feeling cheery bur not quite that vibrantly cheery, you can pair some nice texture-filled brogues with a pleated skirt with a fun pattern and a button up blouse – the perfect outfit for a spring patio or a summer craft beer festival. Getting some solid socks that match the main color of the patterned skirt gives you the perfect way to unite your shoes with the rest of the outfit.

Earthy and Educated Tomboy-Femme Looks

Suppose you love skirts and dresses but you’re more of a “yoga-teacher aesthetic” kind of person? Spring and fall are a perfect opportunity to wear your favorite masculine shoes with thick, warm knee high socks, a mid thigh dress and a cozy cardigan. For casual get-togethers, you have the option of matching the socks either to the dress or to the cardigan, and not worrying too hard about how to unify it beyond that.

Like to be unrestricted? Flow to the beat of your own drum with a summer maxi skirt and a cute tank top, for extreme comfort both in your loose and freeing skirt and your fashionable alternative to flats. Maxi skirts look especially good with some brown brogues, which also pair really well with any wood or faux-wood jewelry you might have.

Fearless Troublemaker Tomboy-Femme Looks

Being feminine doesn’t always have to mean being soft, charming, and approachable. If you’re into the looks that will strike awe and fear into the hearts of timid admirers, the powerful feeling of lacing on some high quality masculine dress shoes is the ideal footwear choice. When you’re out to really break some hearts, pull on a pair of black derby style oxfords, your favorite short skirt, and a black leather jacket. To balance out the short skirt, you can either go totally sockless or else add some dark tights or leggings.

Rather have the leather (or faux leather) on your hips than on your shoulders? Play fast and loose with what we consider menswear by combining a leather skirt and a cute vest – black skirt and grey vest make a great combination. If you’re feeling like you can rock it, this is absolutely the kind of outfit that benefits from a good hat to finish it off. With the masculine shoes to bring it all together, from your head to your toes you’ll be wearing a look that screams “unstoppable”.