The Playbook For The Modern Man

17 Best Oxford Dress Shoes To Buy Under $300

Less than $300 is all you’ll need to play…

Say hello to the most elegant dress shoes for men today. We’re not talking about double monks, simple lace-ups or even loafers – it’s all about the classic Oxford shoes which hails all the way back from the 17th century during the rule of King Louis XIV of France.

What Is An ‘Oxford Shoe’

So what’s the difference between an Oxford shoe and the typical leather lace-up? The lacing system. Oxford shoes utilise a closed lace system compared to the open lace system of a traditional Derby shoe. Additionally, the uppers of an Oxford shoe consist of quarters (rear leather section) and the vamp (separate mid-leather section) stitched over one another. When the laces are tied, the two leather quarters should form a narrow ‘V’ shape. And lace holes? Modern British Oxfords consist of 5 eyelet holes on each side whilst American Oxfords tend to have 6.

Identifying Quality Oxford Shoes

Now that you know the difference between standard leather dress shoes and Oxfords, it’s time to get into 17 of the best and most affordable ones on the market today. It’s not just all about the big ticket names as the focus here is about the shape. We’re going for rounded toe Oxfords which exude contemporary tailoring prowess without that horrid pointy shoe trend that should have died with the elves. It’s an elegant shape which should last the test of time and save you money which leads us onto another good point: How to pick a quality pair of Oxfords.

The pros we spoke to have noted these signs to look out for in the perfect leather shoe.

  • Leather and suede flexibility – the softer the leather, the more comfortable it is on the feet. The downside to this is that it doesn’t last as long as thicker leather constructions which can also be cheaper to use
  • Smell the inside of the shoe – if it smells like glue, you know it’s been made on the cheap with glue bonding as opposed to stitching
  • Smell the leather – a good quality leather shoe needs to smell like good quality leather (i.e. non-synthetic smell)
  • The soles of leather shoes are vital components – high-end luxury shoes often have “hidden channels” where you can’t see the stitching on the bottom of the shoe. It’s a more elegant look which can add to the final cost of the leather dress shoe
  • Leather grading is important – good quality leather should last longer and hold its shape more, especially in a deconstructed shoe like loafers
  • When trying on leather shoes, try to feel the firmness of the inner sole. This will determine how comfortable the shoe is and its general quality
  • Expensive shoes will use a better quality sole that’s designed to last up to three times longer than the average lifespan

And there you have it. Now go forth and grace those feet with our selection of the finest Oxford shoes $300 can score you (some are over $300 due to currency fluctuations).

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J&M Collection Adler Cap
J&M Collection Adler Cap $149
Aldo Patern
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Carlos by Carlos Santana Woodstock
Carlos by Carlos Santana Woodstock $159
Massimo Matteo 6 Eye Bal Cap Toe
Massimo Matteo 6 Eye Bal Cap Toe $159
Kenneth Cole New York Garner Lace Up B
Kenneth Cole New York Garner Lace-Up B $160
Cole Haan Jay Grand Cap Oxford
Cole Haan Jay Grand Cap Oxford $180
ECCO Vitrus II Cap Toe Tie
ECCO Vitrus II Cap Toe Tie $200
3 Wise Men The Clapton
3 Wise Men The Clapton $230
Belsire Blue Ginetto Leather Oxfords
Belsire Blue Ginetto Leather Oxfords $245
Scarosso Giove Oxfords
Scarosso Giove Oxfords $251
Ted Baker Fually Lace Up Shoes
Ted Baker Fually Lace-Up Shoes $274
Ted Baker Quidion Oxford Brogues
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Scarosso Beaumont Black Oxfords
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  • Matt Johnston

    Many of these are not even oxfords, but are derby shoes. The introduction of the article explains quality shoes and oxfords then goes on to list low quality over-priced shoes! What is this? Best way to get a good pair of quality oxfords is to get them on sale or on Massdrop. For example, Loake lists 1880 line models often for under $300 USD, the quality of which will absolutely blow away anything mentioned in this article. Even the most expensive pair on here is not even goodyear welted! Shame!


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