How Should Dress Shoes Fit? – Men’s Clothing Fit Guide – Oxfords, Brogues, Derby, Loafers, Monkstrap


(majestic music) – Hi, I’m Ashley Weston. I’m a celebrity menswear stylist. If you don’t anything about me, click right here. This video is part of my
men’s clothing fit guide. So I wanna talk to you about how your dress shoes should fit. I’ve seen so many articles and videos discussing all the different measurements you need to know regarding your feet like the length, the width, the arch, your toe-hair length. Every little measurement
that you need to know in order to find the
proper fitting dress shoes. And here’s the thing. You don’t need to know any of that. I work with shoes every day, and all you need to know
is your general shoe size. And that’s because every designer has a different definition
of their sizing. So you can be an 11 in one brand, but a 10 in another. Just know your general shoe size, and from there, we’ll figure out and adjust to get the
proper fitting dress shoes. So there’s really only four things you need to know before
trying on your dress shoes. First is knowing your shoe size. I’m assuming that you’ve worn shoes before and you should have a general ball park of what your shoe size is. And that’s what we’ll start with when you try on the shoes because, like I’ve said earlier, each designer, each brand makes their shoes differently. The second point is your dress shoes should fit perfectly the first time. A big misconception is that your leather dress shoes will stretch over time. So if they feel a little tight, then why not just go get them. Leather over time it softens, it gets a little softer,
so it’s not as stiff, but it only gives just a little bit. So you need to make sure that when you first try them on, that they fit already perfectly. The third point is your feet
swell throughout the day. So if you can, when you
try on your dress shoes, make sure to try them on in the afternoon. That way you get a more realistic picture of how your shoes will fit. The last and final point
that you need to know before you shop for your dress shoe is your feet are not the same size. There’s always gonna be one foot that is larger than the other. Make sure that your dress shoes fit the larger foot. It’s better that your shoes are slightly larger than slightly smaller. Now that we discussed the points you need to know before
trying on your dress shoes, let’s go over the things you want to know and do when you’re
trying on your shoes. Number one, the first thing that I cannot emphasize enough is try on your shoes with the socks that you
would be wearing them with. So, I hope they’re not athletic socks, white athletic socks. And I hope they’re not
also thick wool socks or thin socks. You wanna try on the shoes with the socks that you would normally wear. That’s key key key in order to make sure and get a realistic picture of how they’re gonna fit. The second point that you’ll want to know when you’re trying on your dress shoes is the length. So I have this Allen
Edmonds Oxford dress shoe right here to help me
demonstrate this point. So when you have your dress shoe on, you want to make sure that your feet so your toes, hit about right here. So you never want your
toes to fill up this entire space. So if that happens, if you feel any kind of pressure on your toes, like your toes are pushing
up against something, then size up half a size, and if that still feels cramped, then size up half a size again. And that should definitely
fix your problem. The next point is figuring out the right width of your shoe. Most men are, I’m gonna get
a little technical here. They are a D-width. So that’s the width right here. They’re a D-width. You don’t really need to know this because most shoe brands
don’t even specify this, and when they don’t, it’s usually because it’s just a D-width, it’s the average width that most men are. When you put on your shoe, you should not feel any
pressure or scrunching around your feet. So nothing here, nothing anywhere. If you’re starting to feel pressure here, that means the shoes are
not wide enough for you. So what I would do is size up half a size because you don’t wanna throw
off the length of your shoe. See if that fixes the issue. If it doesn’t, then what you wanna do Is either try a different
style in that brand or you’re just gonna have to try that sames style in other brands. But the beauty of dress shoes is, most designers all make similar styles. In the inverse, if the shoe, when you have it on,
if your feet feel like they can literally slide left to right, if there’s a lot of room in there, then the shoes are too wide for you. So try sizing down half a size so that it’s more narrow,
the width is more narrow. If that does not work, and there’s still plenty of room, then again, you’re gonna need to try another style in that brand or go with another brand. One more thing on width. When they’re tied, if
the two pieces right here touch each other, I know a lot of articles say that if they touch, that means the shoes are too wide. In my experience, sometimes some men just have not a lot of meat on the profile of their feet,
the top of their feet, and so that’s why it’s touching. I don’t think that it’s an issue at all. As long as the width of here
by the ball of your feet, right here, this is where it should fit as well as the length. So if these two pieces are touching when you lace them, it’s not an issue. It doesn’t matter. The last and final point that I think is worth mentioning even though it should be a non-issue if you’ve gotten the length and the width
of your dress shoes right is the heel of your dress shoes. When you have your shoes on, laced up, ready to go,
start taking a walk. Take a couple stops,
and your heel should not feel like it’s slipping out of your shoe. If it does, then it’s too
long, there’s too much room. So then go down half a size, and that should fix the issue. Cheaply made dress shoes have this weird, stitching and layering on the back that can really rub at your heel. Do not get the shoes. You do not want to have to go through blisters and all of
that uncomfortableness. It will not soften over time. It will never get better. Instead, save your time,
your money, your sanity and go with another pair, another style, another brand of dress shoes. You don’t ever wanna feel
any uncomfortableness on the heel when you’re walking. All right, so that’s it. That’s all you need to know in order to find the perfect fitting dress shoes. I know a lot of guys out there are definitely hesitant about dress shoes because they feel like
they’re uncomfortable and that’s not the case. You have to make sure the first time you try them on that they are comfortable, and if you hit these points, you will find the perfect fitting pair. Like I said in the beginning, this video is part of my
men’s clothing fit guide. Thanks so much for watching. Check out my website for
more in depth article that goes over all of these
points in more details, and I also include my favorite dress shoes that every man should own. Subscribe to my YouTube channel for more videos like this, and if you like this
one, give it a thumbs up. All right guys, I’ll
see you in the next one. (majestic music)

78 Comments

  • The first link is coming up as a bad url for me.

  • Awesome thank you. I got a pair of dress shoes from Aston grey and had to size down .5 inch. I tried going down a full 1 inch but was getting pressure on the top of my feet when I was walking.

    also another tip when your walking in your dress shoes in the shop or at home. walk on hard floors because you'll be walking on hard floors when your out.

  • Sidebar: your hair looks gorgeous!

  • Great information while also being entertaining. Well-done.

  • I've noticed that when I try on dress shoes and walk with them on I notice little wiskers between the end of the shoe and the bottom of the laces. Is that normal or is it too big? too small?

  • Most of the dress shoes I wear get wrinkles right behind the toe cap. I must have a very flat foot. Do you have any idea what i can do against this issue? Or does everyone have a problem with wrinkles on the top of the shoes?

  • its all about the width! we probably knew that already 😉

  • yeah , but what if I am short with large feet , than i look like a Peter Pan

  • Is 1 1/2 thumb with in the toe area to much? The shoe I tried was really comfortable but there was much space left in the toe box, whilst the same shoe smaller size had a tighter fit but still not uncomfortable had about 1 thumb with left. Which one should I get? Both are comfortable but one is just tighter. They are the same brand and model.

  • I have very wide feet, I can never find something that fits me 😥 I wanna start a shoe company exclusively for wide feet men

  • There's a "d" in width.

  • you deserve so much more subs. thank you so much Ashley!

  • A lot of nice shoes come in a wide version also.

  • Guys, if you're toes fir perfectly but feel tightness on the side, DON'T SIZE UP. Reason why is you'll end up looking like a penguin and the proportion won't look right with your body if you size up. My advice is to choose a wider shoes because they should have that. They have types for width aswell like she mentioned. Nornal is D for example.

  • I enjoy your extremely informative videos. Can you recommend some Oxford brands in the $150-$400 range?

  • I have a very wide feet. Can you suggest how I should purchase dress shoes

  • excuse me, if a shoe is tight, bigger size or the next size wont help, you should try a wider shoe, probably you have a wider feet. how can a shoe which is tight in the front help if u take a half inch r one inch bigger. crap video. i disliked it.

  • What do you think about luxury shoes like Louis Vuitton and Gucci?

  • A informative video, could do without the multiple body shaming jabs

  • Thank you señorita for this information 😉 👍 <3. @Ashleyweston

  • I found out recently I'm a BLITHERING IDIOT and have been buying shoes about a half to full size too big my entire life. I've got like 6 pairs of fancy shoes ranging from allen edmonds to johnston murphy and one day at a shoe store I tried on a half size down and thought "gee, these fit pretty good" and then sure enough I went home, tried on all my other pairs and did some measurements and yep, I wasted so much money. I think I was just in denial all these years because I have tiny feet, I couldn't bear to buy a size smaller than I already am. UUHG

  • Could you make a video on boots, Ashley?

  • Ashley, I just bought a pair of loafers, and there seems to be a little bit of pinching on my little toe. When I feel the side of the shoe, I can clearly feel the bone of my little toe against the leather. I should probably go a half size up, but I feel if I do, my heel may start to slip. What should I do?

  • I'm 19 years old and I never really see guys my age wear dress shoes. Love wearing these kinda shoes 🤘

  • does the length rule apply same with the suede lace up shoes wearing with shorts?

  • you're the best! thanks for this review!

  • >>>I just bought some bostonian oxfords in a 10M… but my normal running shoes for most of my life have been 10.5 or 11… but these bostonian with dress socks fit all the criteria you mentioned in video. this reassures me I'm gonna be okay 🙂

  • thumbs up. just subscribed!

  • wow thanx ashley…
    i just needed this 😊

  • Thanks Ashley! Your advice really came in handy. I had to swap in my Allen Edmonds' two times 'til I found a cozy size. I had to size up to an "E" width. I've never had this problem with any other shoe. I guess the Allen Edmonds are a bit narrower than most other shoe brands–or at least the ones I normally wear.

  • Got my first pair of AE Carlyle's. They were a bit tight midway (10.5D) on the side and AE store said it would break in which was false as you stated. He said it was best he could do since I had flat feet the shoe wouldn't fit perfectly. Wore it first day and was miserable blisters on outer toes. What are your opinions? I did size up half a size (11D) but was too large. Called AE and since they are worn no returns… they agreed with all your points.

  • Very interesting topics you just got your self a new sub gorgeous

  • David Bowie was channeling you my dear…!!!

  • is she talking about sex or do I have a dirty mind?

  • I have so narrow ankle that even to small size still slip on:(. And my advice try shoes on not to tired and not to rested feet.

  • Thanks for all the info. New subscriber.

  • Love you, you're way of making it simple and to the point! Thank you very much…..

  • Thank you so much! All of the shoes I'd been buying up til now had pretty much been too narrow for me but I always thought they would just stretch over time – so much pain, and money gone! Going to buy a really nice pair of brown leather oxfords now I know how they should fit.

  • I have truly long narrow feet- 13B.. My choices for dress shoes are limited to the following: Allen Edmunds; Alden; Johnson & Murphy (Custom); Church- the one company that makes Alden seem budget priced; and Raincourt & Co. NOTE: The best fitting footwear for my feet tends to be upper middle to high end cowboy boots- Boulet and Honcho.

  • you are awesome!

  • i love these shoes , genuine leather made. Just Purchased.

    http://www.amazon.in/Seeandwear-Genuine-Leather-Formal-Shoes-7/dp/B018XWTXVS/ref=sr_1_496?s=shoes&ie=UTF8&qid=1490788421&sr=1-496&nodeID=1983572031&psd=1&keywords=formal+shoes+for+men

  • most men are D width. meanwhile im a 3E. does that mean im alpha af?

  • I found that the photos are just too hilarious hahah XD

  • Hey Ashley! I just recently bought a new pair of Allen Edmonds Carlyles. I question if the length is too long because I notice my back heel starts to slide up a little when I'm walking (thin dress socks, on thicker socks not a problem). Now the thing is I am barely able to slide my pinky behind my heel gap. Is the new shoe just stiff and causing my heel to life up or should I size down?

  • Most companies don't have sizes in narrow to triple wide. Allen Edmonds does, I wear 7 EEE in A/E. Now tell me a brand that does that?

  • Hmmm not sound advice.

  • No Michael in this episode 🙁

  • Stop bullshitting stuff that everyone knows. We all know that if you feel cramped they are too small and that we should try a bigger size. At least you had some good points in the video but the bullshit is just a waste of time

  • i wear 12–13. i don't wanna look like a clown with the extra long dress shoes because of the empty space at the tip. 😢

  • you videos helped me so much, thanks

  • …PRESSURE

  • Have you ever heard Obermain brand? If yes, how do you think about that brand? Thanks

  • Thanks mam

  • great video!

  • People who think dress shoes cannot be comfortable.. I would suggest try a lot of brands n invest in a quality pair of shoes coz I have dress shoes which r at par with my sneakers when it comes to comfort. Try investing some time and money before u buy your pair… Best of luck with Ur shopping fellas.

  • Thank you. Like all women, you're more helpful than a man! 🙂

  • I like how she cradles that big shoe. Just sayin'

  • Did she just refer to herself as a "celebrity" menswear stylist? Lmfao

  • What's the quartet piece that plays at the beginning and the ending?

  • I've been having a hard time finding good fitting shoes. I don't have a lot of money, so I have two options.
    1) Buy brand new, cheap shoes, or
    2) thrift for good shoes.

    I have been having really bad luck up until this past weekend. Just this past weekend I thrifted 3 pairs of great fitting shoes in great shape. 2 x Johnston & Murphy, 1 penny loafer for $3, 1 derby for $8. 1 x Cole Haan loafer for $3. All brown in like-new condition.

  • Nice hair

  • Shoe Size… Duh!

  • shoe size is d m w

  • QUICK QUESTION: I just got Bostonian Nantasket Double Monk-strap loafers [Full Grain Cow Leather, with leather soles], size 9 and 8.5. [In sneakers I'm a 9 or 9.5]
    The 9 feels the best (as I would hope a shoe to fit after having "Worn it in") – This is largely due to size of my arch and top of foot (nearly 3x's your average persons and hump curvature to top of foot). Thus dipping back down to strait at a steep decline. So due to this, the space between toe and front of foot is approx 1.5".
    The 8.5, is like a loose tourniquet at the balls of my feet, and not able to get a finger in between my heel and back of shoe… but the length gap is the most comfortable [1"].
    My natural instinct says to go with the 9, but my concern is that, if it feels now how I'd hope it should fit after a year of wearing them. Will I run risk of a floppy shoe down the road?

    The creasing on the 8.5 when I step is extreme and in multiples, hurting the toes at the end of my smaller foot.
    The 9 offers a faint single crease strait across the front, without touching my toes when I step, and leaves no remaining crease humps.

    What would be your suggestion? (I've tried about 5 brands, these seem to fit my feet the best)

  • I buy shoes like that but it kinda long for me 😢😢

  • when shoes become a little loose over time and the laces close completely, would not insoles solve that?

  • Thank you for your tips.

  • In oxfords the eyelet lips SHOULD TOUCH ! If they don't touch then it looks sloppy and makes it seem like you have fat feet or even worse, some kind of arch bend like bound feet. The sleekest most elegant form for an oxford shoe is for that part to be completely sealed and sometimes you can even slip in and out just with a shoehorn without altering the lacing (specially the ones with lean feet). If you can't find a brand that offers an oxford where the lips close completely, then go bespoke.

  • her nose holes are really large

  • first of all don't wear shoes, sandals are the way to go, without socks of course because your feet need to breathe. Size your feet
    There is plenty of u-tube tutorials on this. Trim your nails. Go to a nail salon before sleeping with a woman they hate being scratched. Okay you gotta wear shoes on your job or it's just too damn cold for sandals. start by your foot size 10 by D ? then 10 1/2 by E shoe size. You can't fit a 1/2" bolt into a 1/2" hole. If there is a shoe maker in your area he may be able to correct a shoe that does not fit well. Yeah try them on your know if they are for you. buy quality you will be a lot happier with a 100 $ plus shoe than <100 $ because I got it cheap. No aching feet at the end of the day.

  • Well, I always have trouble buying shoes of any kind because I am a small guy, always have to go for the smaller size and sometimes those are a little too long

  • Cute

  • Love your videos but it drives me crazy when you refer to shoe 'with'
    It is 'width' here in uk
    I'm done! Haha

  • You're sooo pretty

  • Yup my Oxford just fits fine and not too wide even though that part you mentioned touches, my feet is as you described. Yes not much meat on top of my feet.

  • im us 5 size, any idea what brands shall i go for ? oxford, derby, boots, brogue ?

  • my tip is that i always put on thick socks when i try shoes in the morning, soo thee will ol ways fit in the evening

  • That was actually pretty useless. I'm here because I'm having a hard time determining what my "normal shoe size" is.

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