Dress Shoes for Masculine Presenting Style

I know all too well how challenging it can be to find dress shoes that enhance your masculine presenting style. Over the years I’ve started to understand the importance of quality versus quantity. I prefer investing in a shoe that will last for years versus a pair that I can only wear a few times. With that said, I also grew up with a fashionista mother, who also sold designer shoes, so I’ve learned a lot about buying quality!!

I’m 5’5″ so as you can imagine, I don’t have big feet, which means I can’t even fit the smallest size in men’s shoes. Not every masculine presenting woman has this problem.

When shopping for shoes, I try to find women’s shoes that are based on a mans style/silhouette. For years, that was a struggle, but designers are finally catching up to androgynous and masculine presenting style. This means I don’t have to worry about shoes looking too feminine against my suits or casual wear.

Dress Shoes For Masculine Presenting Style

Whether it’s Corporate, Dinner Dress, Special Occasions, or Casual Dressing there are many shoe styles to compliment every occasion. These days you can also interchange one shoe to work with several outfit styles.

Here’s a look at five styles that every masculine presenting person should have in their closet and where to shop them.

1. Oxford Shoes

In my opinion, the Oxford style is a great starting point when buying a dress shoe. Oxford shoes are extremely versatile! This style of shoe is most often worn with business attire or to a formal event, however, it can also be worn more casually with jeans and a sweater, jacket, or blazer.

There are five types of Oxford shoes – classic, cap-toe, wingtip, saddle, and whole-cut. Some of the most recognizable characteristics of the Oxford shoe are its closed lacing, low heel, long vamp, and deeper toe box. This example (Paul Evans The Cagney Cap-Toe Oxford in Oxblood) is the most common style of the Oxford.

Dress Shoes for Masculine Presenting Style

Shop oxford shoes:

Women’s Shoes

Dress Shoes for Masculine Presenting Women

The Office of Angela Scott Ms. Baker Oxford ($495) The Office of Angela Scott Mr. Evans Wingtip ($525)

Church’s Burwood Wg Oxford in Black ($950) Church’s Burwood Wg Oxford in Sandalwood ($950)

Grenson Rose in Triple Welt ($705) Grenson Martha ($445)

Men’s Shoes

Beckett Simonon Dean Oxfords in Black ($209) Beckett Simonon Yates Oxfords in Oak ($209)

Church’s Dubai Oxford ($950) Church’s Fairstead Oxford ($995)

Grenson Toynbee ($580) Grenson Stanley ($445)

Thursday Boots Broadway ($168) Thursday Boots Aviator ($175)

2. Derby Shoes

Derby shoes are often confused with oxfords even though they are quite different once you learn about their distinctive characteristics. Unlike Oxford shoes, Derby shoes have an open lacing system with the eyelet facings stitched on top of the quarters. The quarters are sewn on top of the vamp, comprising three specific pieces: a vamp with the tongue and two quarters. Derby shoes also have an elongated or rounded toe.

Shop Derby Shoes here:

Unisex

Dr. Martens 1461 Smooth Leather Shoes ($120) Dr. Martens 1461 Mono Smooth Leather Shoes ($120)

Women’s

The Office of Angela Scott Ms. Presley Derby ($495) Grenson Evie ($705)

Tod’s Lace-Ups in Leather – Black ($595)

3. Loafers

Loafers are slip-on shoes and are quite versatile. The penny loafer is the most widely recognized and commonly purchased loafer. However, bit loafers have become a favorite over the years after Gucci re-introduced its 1953 Horsebit Loafer in leather as well as its newest horse-bit loafer, the Gucci Jordaan leather loafer.

Loafers are the ideal shoe for going sock-less which also makes them a perfect shoe for warm weather. Dress them up or down with shorts, linens, jeans, or trousers. This smart and dapper shoe is best matched with a smart yet casual look.

Shop Loafers here:

G.H.Bass Whitney Lug Weejans ($135) Sebago Classic Dan Woman ($245)

Blackstock & Weber The Ellis Penny Loafer ($345)

Stuart Weitzman Palmer Sleek Loafer ($450)

Gucci 1953 Horsebit Loafer in Leather ($830) Gucci Jordaan Leather Loafer ($850)

4. Monk Straps

If there is a shoe that masculine presenting women absolutely love it’s the double monk straps!

There are three different styles to the monk strap shoes: single, double, and triple buckle straps across the top of the shoes instep. Today I’ll focus on the single vs. double monk straps.

Single Monks

Instead of shoelaces, the single monk strap has one buckle that comes across the instep to tighten. Since the shoe doesn’t have laces like an oxford it can be considered as a bit non-traditional. However, the shoes have similar properties and characteristics as dress shoes. In my opinion, the lack of laces and details gives the single monk strap a sleeker look. Plus the single buckle and easy slip-on functionality allows the shoe to present in a more formal manner than a loafer.

The tongue of the shoe is wider than an oxford because there are no laces. The quarter also overlaps the tongue. Once the shoe is fastened, the three layers combine to help to secure your foot.

Double Monks

The name speaks for itself. The double monk strap has two buckle straps. The significant difference between the double monk strap and the single monk strap is the appearance. The details of the double monk strap (i.e the extra buckle and metal) makes it an eye-catcher. You know what they say, the devil is in the details!

The double monk shoe is considered a very versatile shoe. These can be worn in a casual yet sophisticated way with a blazer and trousers or jeans but work best with a suit.

Just remember, while this shoe is pretty versatile and works really well with a suit, it’s not considered formal and therefore, not recommended for ‘true’ formal events, especially those with strict dress codes. Black oxford shoes are still considered the ‘more appropriate’ shoe for formal settings since dress shoes with laces are still more conventional and traditional. I might not follow all of the ‘traditional’ dress codes, but I wouldn’t wear double monks to a black tie or business event.

Shop Monk Straps here:

The Office of Angela Scott Mr. Colin Monkstrap ($495) The Office of Angela Scott Mr. York Monkstrap ($525)

Church’s Lana R Monk Brogue ($995) Tod’s Monkstrap in Leather ($645)

Carmina Women Double Monk Strap 1645 Madison ($415)

5. Chelsea Boots

If you’ve already added a pair of oxfords, loafers, and monks to your wardrobe then your next pair to complete your collection is a pair of leather dress boots. Laceless boots are classy, minimal, and timeless.

The Chelsea Boot is a slip-on silhouette with an elastic ankle that makes it flexible and comfortable. Chelsea boots are traditionally made of leather, but can also be found in suede. These boots can range from semi-casual to dressy, making them the perfect boots to wear to the office or a casual day/night around town.