The Oxford Dress Shoes – Men’s Wardrobe Essentials – Best Mens Dress Shoes

(classical music) – Hi, I’m Ashley Weston. I’m a celebrity menswear stylist. If you don’t know anything
about me click right here. So this video is part of my Men’s Wardrobe Essentials Series. I wanna talk to you about The Oxford Dress Shoe. Every man should have some
Oxford Dress Shoes in his closet. They are versatile. They work in nearly all formal occasions and they are your go-to shoe for suits, or if you want to wear a
pair of dark wash jeans. Then you can throw on a sport coat, Harrington jacket, leather jacket, button down shirt, polo shirt, a bunch of different things. So they work in so many situations. When you imagine a guy in a suit I guarantee you he is wearing
a pair of Oxford Dress Shoes. They are the quintessential dress shoe. I just wanna clarify something. Just because it’s black or brown and leather, does not mean it
equals an Oxford Dress Shoe. I see so many men out there wearing these great suits. I’m looking, well fitting suits, but I look down and they’re wearing these horrible, square toed dress shoe. Whether it be a slip on, lace up, but they’re some kind of variation of an ugly, square toed shoe. Burn those, you should
never, ever, ever wear those. Instead you wanna go
with a black and brown, lace up, round toed, leather dress shoe. Let’s answer the age old question of to cap-toe or not? Well, I’m really split 50/50 on this and so are my clients. Some love a cap-toe and some don’t, but the beautiful thing is it really doesn’t matter
because there is not a single occasion where you would choose a cap-toe over a non-cap-toe. Whatever you think is best and whatever you like
more, go with that one. Should you go for quality or value? With dress shoes always, always, always invest in them and go for quality. With that being said
there is one exception. Ask yourself the question, how often will you be wearing
these Oxford Dress Shoes? If you’ll be wearing them more than a handful of times a month, then you definitely want
to invest in a great quality pair of dress shoes. They will last you many years and look great the whole time. If you’ll be wearing them sporadically like once a month or even less, then definitely the argument can be made, you don’t have to go all out and spend a ton of money on them. Which colors should you get? So, every guy should have
two Oxford Dress Shoes. One black and one dark brown. That will get you through every situation and every formal, semi-formal
outfit that you can possibly wear in your closet. I have Tommy here to help me demonstrate the best ways to wear
your Oxford Dress Shoes. Thanks so much for being here. – Thanks for having me. – So the first outfit that I have him in is in this Fred Perry Harrington
jacket, this grey sweater and white button down
shirt by Brooks Brothers. I added this black leather
dress belt by Allen Edmonds with these Burberry Brit jeans and then we finished it all off with these Allen Edmonds Black Oxford Dress Shoes. So I put him in this first outfit. Let’s go change him for the second outfit. I’ll be right back. (classical music) And we’re back, so I’ve got Tommy here in this Camel Coat by Brooks Brothers. As well as this navy v-neck sweater and blue Oxford button down dress shirt both by Brooks Brothers. I added this brown leather
dress belt by Allen Edmonds with these grey trousers
by Brooks Brothers and we’ve switched his Oxford Dress Shoes for these brown pair by Allen Edmonds. That’s some of the
different ways you can wear your Oxford Dress Shoes. A black and dark brown pair will get you through every situation and seriously, they look
good with everything. Just a quick note though, please, please, please always make sure to match your belt with your dress shoes. Please just do this for me. I promise you it will make everything look so much sharper. This video is part of my Men’s Wardrobe Essentials Series. Check out my website for
a more in depth article that includes all of my
favorite Oxford Dress Shoes. Subscribe to this YouTube
channel for more videos like this and you know what, while you’re at it, if you like this video give
it a thumbs up, pretty please. All right my stud muffins out there thank you so much for watching and I’ll see you in the next one. (classical music)


  • I feel like a black closed lace oxford and a brown open laced oxford (derby) is better since I don't have the cash to drop it on two closed lace oxfords.

  • AE is awesome

  • That coat! I'm dying.

  • wow great vid keep it up ashley

  • Where's the code?

  • you didn't mention about the close lacing systems of an oxford!

  • Thanks a lot Ashley for this great video. I have a quick question on Oxford Shoe. I recently bought a pair of Oxford Shoe. Even though the shoe is great, it does not have a wax finish (shining) on it. Is it expected that the dress shoe should always be shining?

  • Great video. The first point about not having squared toes shoes is so on point. The point about utility and rather to invest in quality vs. value was also spot on and not addressed often enough. Having a live model sure helps in the actual visualization. Just my two cents on the first one. It seemed quite casual overall so the Oxfords seemed slightly out of place, but that second one went together quite well.

  • You are such a beauty, Ashley! All the love! 🙂

  • Thanks a lot Ashley for this great video.

  • A very good video, but by definition the cap toes are the less dressy option (jeans, chinos) than the ones with non cap toes (slacks, suits). The general rule is the more complicated the less dressy the shoe.


    Would these be a good pair to buy?

  • I honestly think an oxford is a bit too formal for a pair of denim, no matter the wash. I would personally go with a derby. Derby's are a lot more versatile, you can pull them off with a suit AND denim.

  • I personally dont like the black oxford shoes that much. 9 out of 10 will wear them in the room… you'll never get any compliment or notice if you look like everyone else…

  • Alright! I promise Ashley to match my belt. I just bought a pair last night with square toe online 🙁 they're going straight back, not even gonna open it.

  • thank you thank you thank you !!!

  • I think the cap toe looks a little more casual. Also some people like the square toe shoe. I personally don't mind it With some loafers. I don't think people should "burn" then if that's all they own 😉 lol. Love you videos btw. Thank you for all the information!

  • I have Black and Dark Brown Oxford dress  shoes as you have stated. In my experience Allen Edmonds makes the absolute best. Not cheap, but WORTH every penny.

  • What do you prefer: leather or rubber sole?

  • Hi Ashley, it's been a pleasure splurging on all your videos over the weekend! I'm a fan. Quick question, what are your thoughts on double monk straps and how they should be worn? Thanks in advance.

  • Is this a ugly square toed shoe. Should I keep or return. Cole Haan Montgomery monk strap

  • A red/ burgundy/ oxblood, will add an additional layer or depth to a man's wardrobe once the 2 basics are covered. .. Like you covered so elequintly 🙂

  • I've a question about men dress shirt most people go to color are white and oxford blue so what about the other color are they only meant to be worn in Proms ??

  • Hey Ashley. What do you think about Chelsea boots? I love them. They're currently my favourite footwear, but what do you think about wearing them in more formal situations?

  • Are black oxfords too formal for the office?

  • Hi Ashley, I work in an environment where you need to wear dress shoes but frequently crouch down, which ends up bending/creasing the top cap area of the shoes. Do you still recommend Oxford or should I maybe invest in an alternative? (I heard Cole Haans is amazing)

  • Black shoes here are an epidemic.
    Almost everyone wearing them square toed.
    And that's not the worst part of it.
    Those square toe shoes looks are too long.
    Like shoes worn by elves, the tip isn't pointy though but square toed..
    Imagine, Long Square Toed Black Leather Loafer Shoes..

    Thank god I only worn a normal square toed black derby and I pledged that I never wear them again. Its covered in dust now and I might throw them away, it's cheap though.
    I even bought a dark tan cap toe oxford..

  • Just as with the leather jacket being able to be more formal than i imagined. I never imagined Oxford dress shoe could go with Jeans! so cool. I also never imagined how wonderfully straightforward the styling is, making choosing a slim elegant one much EASIER than i originally thought!! Brown Oxys next on my wishlist. Just got the white Oxy button down shirt ordered today. Thanks Ashley!!

  • This video made me finally decide to buy a quality shoes. Good thing, there's an Allen Edmonds store in SF. I usually wear size 10 US shoes, but the guys at AE recommend that I wear size 10.5. The Black AE Carlyle looks so good in person & it's so comfortable to wear. I want to buy another quality shoes, what other brand can you recommend Ashley?

  • When your article says "brown/cognac", is cognac just a lighter brown? How light can you go for an "essential" shoe? I am thinking of AE's bourbon or dark chili color. Thanks!

  • Hello Ashley, for the AE brown oxfords do you suggest the Brown Burnished Calf or Chili? The Burnished Calf appear darker and to my eye the Chili most closely matches the shoe displayed on your site. Thanks much.

  • I just wanted to point out that you didn't actually explain what defines an oxford shoe so people know what to look for. Also, in your article's recommended 'go-to oxfords for clients' you've included a set of derbys in there – the Christian Louboutins. The thing that defines an oxford shoe is having a closed lacing system.

  • She is right about the square toed shoes…Hideous!

  • Donate them, don't burn them.

  • Ashley, I like these derby shoes by h&m:

    Would you say they're okay as a dress shoe.

  • wtf. tommy is well handsome.

  • Great job Ashley.

  • Love your video! I'm 50 yrs old now. But I remember when I was in my teens(circa 80's) my Dad gave me a black wing tip and a brown cap toes( all hand me down Aldens). My friends were all laughing at me every time I wear them with jeans! Look at them now they're all stuck in those lousy square toed shoes!!! FYI. Those Aldens are still in perfect condition!

  • What're your thoughts on Cole Haan? I never see you mention them in the "budget" lists for dress shoes, but I've always found them to be pretty stylish and incredibly comfortable for their price point

  • what are your thoughts on black Oxford's with tan leather sole that can be seen from the side

  • These videos seem to always assume that money is not an object, and all we have to do is go out and shop anytime we want. I wish I lived in that world. And I will never own brown shoes. Brown shoes equal brown belt; brown belt equals traumatic childhood memories . (Yes I know, TMI)

  • I have seen square toe shoes that throw oxfords under the bus and also the man makes the shoes. Not everyone can pull of square toe shoes just like the square shape is not applied properly to the shoe design.

  • How about a wingtip dark brown version?

  • brb, off to burn my square toed shoes…

  • luv u Ashley!

  • You know what's sad? A lot of companies constantly mislabel derbys as oxfords.

  • Hey, Ashley would you say Johnson and Murphy is a good brand for a decent pair of oxfords? I'm trying to decide between those or paying the extra for Allen Edmonds.

  • I have to say, I would love to play dress up with Ashley..!

    But back to the shoes.. I did a bit of shopping this last Black Friday and Boxing Day and bought four pairs of dress shoes.. I originally bought five pairs, but returned one because I didn't notice the squared toe on one.. LOVE my Oxfords..!! =) ALL except one pair were 50% off..!! I was almost in tears putting items on my wish list, waiting for the next sales.. 

    I swear, I saw about 30 ties I wanted.. haha..

    Don't even start on shirts or suits.. But now I'm rambling..  

    Waiting patiently for Black Friday and Boxing Day again..!!

    Love your videos, Ashley..!!

  • I'm confused about what type of oxford could be worn with jeans + shirt for music playing and with jeans + T-shirt for more casual moments. Are wingtip oxfords more apropriate?

  • she called us stud muffins :]

  • Hi! I've enjoyed the videos. Have you ever reviewed To Boot New York shoes?

  • What happen to cordovan? Nobody wears cordovan no more?!

  • Captoe is less formal than plain toe. Edward Green=John Lobb>Crockett Jones>Church>Cheaney. AE overpriced and way down on quality compared to the Northamptonshire shoemakers.

  • Hi Ashley, I'm looking to update my shoes and get the Oxfords you recommend as well as the dress boot. My question is; I fell in love with John Lobb shoes however those are way out of my price range. I'm considering going Crockett & Jones for all three but was wondering your opinion. Should I go with a $200 Oxford and save the money, and use it else where, or just go for this Crockett pair. The shoes would be worn 3-4 times a week for work for a business or business casual look. I'm not one for brand names but man those John Lobbs were awesome when I tried them on. I'm thinking of just treating myself and just going with a more inexpensive brand. Thanks for the input.

  • "They are VERSITILE"… Shows a loafer. Lol

  • Very informative video. Thanks!

  • Ashely thank you for helping me improve my appearance! I greatly enjoy all your videos and respect that you do not promote sponsored items, instead promote your perspective. More gansta Ashley please! lol

  • I really want to hear once JUST ONCE what the heck he said to her when they meet 😀

  • Am I the only one who thinks she has crush on the model?

  • Tuxedoes: Always plain toe, never cap toe


  • You are a ton help – I knew you would have strong opinions! 😎

  • Saddle shoes master race

  • Respect And Love Leaned A Lot From You Mam

  • Legal!

  • Stole from rmrs

  • Your intro reminds me Harry Potter. 😀

  • Can you have some African American men models so I can see what I look like in the shoes or clothing. Thanks nice videos

  • I want Tommy. >.<

  • Not all 'squared toe' shoes are bad tho (It's called bicycle toe). But most of the time they're cheap shoes designed to fit even the widest of feet (so they don't lose sales) so obviously they're mostly hideous due to bad designs, chunky lasts and low quality materials. BTW, in oxfords the non-cap toe is the most formal certainly.

  • Please forgive my ignorance on the subject. In the military we wear bates dress shoes with our service uniform, will these work in a nice suit as well?

  • I disagree with pairing the jeans with black oxfords. It’s a clash of formalities. If you’re wearing jeans the most formal oxfords you should be wearing are brown full or half brogues. Save the black oxfords for formal wear.

  • Oxford is a brand, so what is she talking about?

  • what about the shape? How should the pair of shoes be shaped?

  • Can I wear this for my school, my uniform is black pants and white polo

  • What's up with that Batman intro music lol

  • Great clip and subject. I personally prefer black 'no cap toe' Oxfords as I like the 'clean lines', plus I like the 'pointed' closed lace holes at the bottom. I'd just have one pair as described as I'd only use them when wearing a Suit and Tie. I don't actually own any Oxfords yet but I do have a pair of black RM Williams 'Tambo' (extra wide 'Craftsman') Chelsea style dress boots that can be worn with either a Suit and Tie or various Business Casual/Smart Casual (jeans) combinations. I too match the leather belt colour with leather shoes colour; kind regards..

  • Great video as usual Ashley! What shoes do you recommend for a black tie tuxedo and white tie tuxedo?

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