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


  1. 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.

  2. 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?

  3. 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?

  4. 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.

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

  6. 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.

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

  8. 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.

  9. 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

  10. 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?

  11. >>>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 🙂

  12. 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.

  13. 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.

  14. 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.

  15. 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.

  16. 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.

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

  18. 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?

  19. 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?

  20. 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

  21. 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. 😢

  22. 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.

  23. 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.

  24. 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)

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

  26. 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.

  27. 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

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

  29. 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.

  30. 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

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

  32. What happens if the back of the shoe has a tiny bit of wiggle? It doesn't come off but its not snug on my back foot that is with thin socks ( i will try it myself with medium thickness socks). It fits perfect everywhere else though.

  33. Mam, with all due respect you in all your videos suggest to go for a round toe and avoid square ones but in this vlog the very 1 shoe is a square toe

  34. That’s something I have always said, shoes shouldn’t have to be worn in! They should feel comfortable the first time you slip them on or they are not right for you! Thank you Miss Ashleigh

  35. I have a heel slippage issue on my tassel loafer. If I pick lower size, the width doesn't fit on me. Would putting a kind of heel pads would help?

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