OR

How to Wear Flat Oxfords

Personally, I have always enjoyed the look of flat oxford shoes. To quote hubby Greg: “They are VERY cute”.  But there is no doubt about it: flat oxfords shorten the leg line and look masculine because they are flat shoes with high vamps. Unless you have a proportionally long leg line they aren’t the easiest shoe to wear.

With some experimentation you can balance out the masculine vibe and shortening effect. Here are some things you can try:

  • Pair them with tapered pants, jeans or ankle length leggings: Showing off the entire shoe when wearing pants, jeans or leggings somehow makes them look more feminine. When sporting perfect pant lengths with wide legs or bootcuts, the tips of the shoe peek out while the rest of the shoe is covered. This looks more masculine to my eye. Of course, the masculine look might tickle your fancy so by all means wear flat oxfords with wide hemmed pants if you prefer that visual effect.
  • Reveal skin on the foot: Sometimes, allowing a bit of skin to peek through between the vamp of the oxford and the hem of the pants keeps things feminine. That’s why I like to go sock-less when I wear my oxfords with tapered jeans. Although it shows more skin, I do not cuff my jeans when wearing flat oxfords because the horizontal cuffs and finished length of the jeans are too leg shortening for my tastes. Instead I leave my skinnies scrunched.
  • Raise the hemlines of skirts, dresses and shorts: This visually lengthens the leg line. I’m not one to wear short hemlines, but a couple of inches above the knee works well. Baggy short shorts work particularly well with flat oxfords because they showcase most of the leg.
  • Voluminous pieces: Unstructured items complement the look of flat oxfords. It’s not a slam dunk, but short sack dresses, breezy blouses, boyfriend cardigans and baggy boyfriend blazers like to be paired with flat oxfords. Somehow, surrendering the waistline is key.
  • Cropped jackets: Boyfriend blazers work beautifully with flat oxfords when worn with tapered jeans, but cropped jackets work well too. Wear a cropped jacket over a flared skirt or dress, tapered pants or with walk shorts. The short hem on the jacket visually draws the eye to the waistline which raises the line of the leg.
  • Add hosiery: Keeping a low contrast between the colour of your legs and the shoes creates a longer leg line. For example, wearing black opaque tights with flat black oxfords is visually lengthening because there is no contrast between the oxfords and the leg. Wearing black micro fishnets with my oxfords keeps the contrast low too.
  • Choose a low contrast shoe colour: Sometimes, opting for nude, metallic, light grey or light brown flat oxfords works better with dresses and skirts because there is low contrast between your leg colour and the shoe. It can also soften the integrity of the shoe, making it more feminine.

A combination of these tips will also work in an outfit. It’s really up to you and your figure flattering priorities. If you like to keep a long leg line as I do, these tips will help. If sporting a shorter leg line works for you, wear flat oxfords with just about anything.

Although flat oxfords are an acquired taste, adding them into your current wardrobe mix can change up the look quite dramatically. They bring both an arty and an androgynous element to your style, which can be appealing. And the comfort factor is pretty compelling too – after all, my flat oxfords saved my feet at Fashion Week!

You might remember these outfits from my recent Fashion Week posts. And that’s forum member Tara peaking over my shoulder in the first picture. Adorable!

Comment RSS

52 Comments on...
How to Wear Flat Oxfords

But HOW does one wear your Oxfords sockless, without a) blistering your feet to hell and b) getting the shoes all manky and sweaty?

I have a pair and love the way they look sans sock, but there’s no way I can get through the day without socks.

Angie, I’m very interested in this look but I’m afraid that I’m too short to pull it off. Thanks for the tips.
PS – I thought you hated opaque tights!

I always love ‘how to wear’ posts, and often find myself coming back to them weeks/months later to put them into practice. This is one of those – thanks Angie! And lovely to see those pics of you again.

I love the look on you! I think the black and white of the shoe helps lighten it up and balances so well with your hair and specs. Have often wanted to try this look but will now!!

Love these on you, Angie – I like them best with pants, but you completely pull off the flat oxfords and dress look, too. Not an easy feat!

Great look on you Angie. I am still on the fence whether or not I will embrace this look. I like it with skirts and dresses.

Great tips, as always, but I’m afraid I can’t be swayed from my anti-oxford stance. They’re just not my style and have no appeal at the moment. But I’m sure this post will be invaluable to the *many* oxford fans who will be sporting more fashionable footwear than I this season! :) Enjoy the styling possibilities, ladies!

I like my oxfords, but feel that they make my feet look really long so I only ever wear them under bootcut jeans and trousers. I might try them with dresses now and see how it turns out.

Love them on you Angie but I think my relatively short legs would really suffer with these. I am on the hunt for some heeled oxfords to satisfy both aspects there :-)

I love oxfords and really want a pair. Does anyone know of a pair that have arch support? thanks!

You look so great in them Angie! thanks for showing us how to wear them.

I love oxfords, and I already have 3 pairs, mostly wear them with pants.

Love all of these looks on you. Thank you for the suggestions on how to wear the oxfords. I’ve been looking at them for a while now and I just couldn’t figure out how to make them work for me. Now I think I’ve got it.

Thanks for the kind words.

Lex, have you tried footies? I don’t wear them but they might work for you. I have found extremely comfortable flat oxfords – no rubbing or blistering sans socks at all. And I don’t seem to get damp feet. Is that weird?

Blonde Ambition, *hate* is a very strong word and I’ve never said that I hated opaque tights :-) . I prefer not to wear them, and I also believe that they are often worn in unflattering ways – but they can look great when the variables of the ensemble are in harmony.

Debbie, flat oxfords are closed shoes and you should be able to pop in your orthotics for arch support.

i think i would have a very difficult time pulling off this look with my wide calves, increasing my squatness.

I find that with flat oxfords, I prefer the look of one with a slightly lower vamp, which is easier to wear with things like skinny pants and is less leg-shortening. I prefer a bit of heel on oxfords with a higher vamp.

You look amazing in those adorable oxfords.!!!

I would be most likely to try black oxfords with black opaques…nice suggestion. I think I would be in my comfort zone with that, plus I think it looks really fab.

Those oxfords are SOOOOO cute and I am SOOO tempted, but I don’t think I can wear them as effortlessly as you do. Big feet plus chubby legs probably isn’t the greatest combination for these shoes… right? How’s the width on the Fitzwells? My size is only available in WW which I think would be too wide for me (I usually take normal widths). Sigh. LOVE them on you. I think I will have to live vicariously through you…

You look lovely as always Angie! Great tips to wear oxfords.

I have oxford-inspired flats that is nude and chocolate brown. It makes it closer to my skin tone so it forms a lean line when I leave some skin peeking between the shoes and my clothes. I wear them with shorter pants and skirts.

What a great how to wear post! Angie, you break down tricky fashion styles into such clear, manageable chunks that now even I am tempted to try oxfords. :) If I did, I would probably go the route Taylor mentions ~ black oxfords paired with black opaque hose.

I’m not sure this is something I will attempt to try, although I think I could get away with the shorter leg line at my height. Somehow it seems to youthful/tomboyish for my advancing age (hate how that sounds) or is that some weird notion in my head?

Angie, you make every trend/fashion statement look so appealing. Any style you fashion for us makes me want to jump right in and give it a try, just not sure if I should, if that makes sense.

And let me throw in another plug for the Frye oxfords, which have a bit of a heel, but still retain the menswear look because it’s not a feminine heel like the Miz Mooz oxfords.. :) Sorry I don’t have the right shoe vocab – I’m sure there are words for every kind of shoe heel.

Diana, heeled oxfords with lower vamps are definitely more leg lengthening.

Carole, every 50-plus year old on our forum could pull off wearing flat oxfords in an arty and sophisticated manner. I 100% believe that. I’m waiting for San to post her looks and hope that Greenglove and Debbie climb onto the flat oxford bandwagon too. Our lovely Taylor and Kyle will sport the heeled versions with sass :-)

Alaskagirl, I understood your shoe vocab perfectly.

Marianna, I found the Fitwells to run regular in width. Bummer about your size being unavailable though. I can see you sport these and chunkier silhouettes too. You are the captain of Team Flats – you must have flat oxfords!

I would never consider this look for myself but you and your pictures are so persuasive!:-) I have been eyeing those oxfords of yours but they do not have my size…:-(
I have the same concerns as Marianna about feet and calves size being emphasized with these shoes but you know what? I waqs also concerned that wearing skinnies or surrendering my waist will make me look bigger and I was wrong! I just trusted you, tried it out and there is not going back for me now! Maybe the same thing will happen with those oxfords – I just need to get my hands (or feet:0) on them!
You don’t know until you try – this is my fashion motto now!

The captain is working on it… just need to find the right pair. :)

Cap’n Marianna, when you find them give me a whistle!:-)

I love oxfords, and have been wearing them for years with trousers and boot cut jeans. It’s thrilling to have so many options out now. I have a couple pair of saddle shoes, a couple pair of Hush Puppies and some others, but that didn’t stop me from buying the Fryes that alaskagirl recommended.

My issue with flat oxfords is just finding a pair that I can wear! I’ve given up the search. If I run across some, great- but I am not ordering any more.

Love them – thanks Angie for sporting them and giving us ideas for these cute shoes. Looking forward to wearing mine this fall and winter!

This is a great post, as usual! I love how you embrace these oxfords and pair them with dresses as well as the more-expected jeans!

*waving to Tara, peaking over your shoulder in the photo*

Thanks for this informative “how to,” Angie. I’m totally smitten with my new and very expensive oxfords and I’m excited to figure out how to wear them often enough to get my money’s worth!

LOVE this post, Angie! I have been wearing oxfords for many years and adore the look AND comfort. Thank you for even more inspiration!

I do wear Peds (footies) with my oxfords. I just can’t do the sock-less thing…

LOVE LOVE LOVE the oxfords and purple dress! Absolute KILLER style.

You look amazing in “your colors” Angie.
I bought the Fitzwell’s just like yours without realizing that you are bookending your hair color. Do you think I should trade them for a pair closer to my leg color or hair color?

Now for a confessional. I was frustrated looking for a pair of brogues about the time NAS rolled around so I ordered men’s wingtips in cognac. It seemed like a good idea at the time. We used to wear men’s desert boots all the time when I was a teen. The wingtips are built alot like the old saddle oxfords only much better looking IMO. Now I am second guessing my wise idea after reading your tutorial on keeping them feminine.
http://shop.nordstrom.com/S/31.....tback=1311
Looks similar to the Church’s for women no?
http://www.net-a-porter.com/product/48594
Net-a-Porter advertises many pair of nice oxfords but they seem to be sold out always.
I did manage to snag these which are so pretty being a pearlized white.
http://www.net-a-porter.com/product/79256

With my narrow shoulders, big boobs, round hiney, short stature, long hair, and small frame, there is basically NOTHING masculine about me. You could put me in a 3 piece suit and fedora and I would still look girly as can be (I always thought it would be fun to wear a tux to my own wedding and have my hypothetical to-be hubby wear a gown. I do like a bloke with a sense of humor!)

I do not worry about oxfords looking masculine. That’s the whole point! Sure I wear them in girly ways, but I love love love the cheekiness of dressing like a boy. Who knows, maybe I’d like it less if I were less girly-looking. These are great tips and great outfits and I don’t wish to trivialize that. I guess I’m ok with being a mild crossdresser :p

BTW thanks for including Greg’s approval as part of this post. So many women think men only like heels but I always seem to get the most compliments when I wear shoes with personality, and they really aren’t very feminine and sexy at all. Unless of course you have a flat suede moccasin fetish.

Great post! I think you totally nailed it. I sent this off to my mother, who just ordered these Fidji’s in ‘hazelnut’:

http://shop.nordstrom.com/S/3073561

I have worn mine (black Frye’s – another Frye oxford fan!) with wide leg jeans and I totally agree this is a more masuline look, but I like it once in a while. I am wearing mine today with straight-leg charcoal cords (scrunch at the bottom, but no skin showing – the scrunch covers the top of my foot) and I LOVE the way the look for Fall. It’s one of my fav looks.

http://outfitdiary.blogspot.co.....color.html

Angie, all of your oxford looks are cute as can be. Thanks for showing them with skirts – this is a look I need to work on.

Ah ha! This is exactly what I was looking for! I just got a pair of sand-colored, sueded oxford flats that are super comfy and cute, and I was having a hard time wearing them with anything.I was thinking I’d have to return these cuties, but I’ll give them another try with these tips!

I love the look on you and hope many others try it out, too. I myself will probably forego it; not because I don’t like it but because of my big feet (size 9 with a body height of 5’3”) I know that such styles, just like Converse, easily look like enormous duck feet, especially when fully exposed (which I agree is the nicest look) and I lack the patience and the funds to experiment until I find the right pair…

They look absolutely adorable with tapered pants!! My fav look by far!!

These pics are so inspiring. I love all of your looks Angie! Oxfords are defnitely for me. I’ve got several pairs – and loved wearing them with sun-dresses this summer. Angie – I’ve basically got the identical outfit that you are sporting in pic #2 – except my trench is a berry color and my LAMB bag has more of a blue, pink and yellow print. I can’t wait to “copy” this look!

I like the look on others but prefer a heeled oxford on myself. I have a pair of brogues that I never wore and finally gave to goodwill! It just doesn’t fit my style. If I’m going to shorten my leg, I’d rather wear cropped pants!

Great advice there Angie. And the pics again! You are killing me with temptation every time you post these shoes, I love them on you. They would be wonderful to wear to work as well if they are both comfy & fully closed. So if the white in the black&white pair serves to bookend your look with blonde hair, would it also work for someone with dark hair too?

Great post! I’ve been eyeing this trend for a while now (oxfords seem to exude an artsy vibe), but have been so clueless as to how I can wear it til today! You look so adorable in those outfits. Oh, and I absolutely love your palette, Angie! If only we could wear coats in the Philippines, I would most certainly don something that color (instead, I opted for a cropped motorcycle jacket in a similar citron color, haha). Keep up the great work :)

I find this look so practical for my local area, I’m often dealing with rain, cobbles and a buggy. My oxfords recently began looking too tired so I’m actively seeking a new pair. I wore my oxfords mainly with short(ish) dresses and skinnies. I guess I was following the rules without knowing it.

Angie, you are the ultimate oxford role model, I always found my oxfords to look sightly casual but you are showing business casual looks are achievable.

Lovely outfits! You make oxfords look feminine and leg flattering!

You look adorable in your oxfords and have given us great tips. These are the shoes my doctor wants on my feet but I’ve not felt fab wearing them. You’ve given me hope that it’s doable with style.

Great tips, Angie. I may try the look now that I have some guidelines.

You look so fab in those outfits!

First of all, you look stunning in all of your pictures Angie, and I feel privileged to have seen you in the first outfit in person. Those are fab oxfords and great ways to wear them.

This is such a useful article for me. I love the idea of flat oxfords and would love to get a a pair, but have been trying to figure out if I could get get them without getting anything else to make them work, since my clothing budget has suffered a serious blow lately. This article is amazing for help with hat as well as what color to get if I decide to.

[...] loved the concept and was sold as soon as she tried them on, but was still a little unsure about how to wear them. When we matched them up with her Gap straight leg jeans and new dresses, everything fell into [...]

I was on vacation when this post originally was uploaded but caught up once I got back in town, and I think I’m going to keep this post saved to my favorites on my browser for quite some time. Since I’m just learning how to wear flat oxfords – and even before I bought them – I keep coming back to this post for more ideas. Thanks again for posting such a fab list!

Can I ask about your eyewear? I am assuming your glasses are prescription, since you are always sporting a cute pair… Are you sunglasses prescription, as well? I have an adorable pair of fuchsia and teal glasses, not unlike the black/white pair you wear, but I never leave the house in them because I am “legally blind” (-7.5) and good prescription sunglasses cost a fortune. Plus my prescription still gets worse every year, so I would be paying for new lenses in glasses and shades yearly. Any advice? TIA!

BTW, I adore you hairstyle. I wear mine the same way and it’s encouraging to see someone so awesomely fashionable rocking super-short hair!

hey @lex the fcomment at the top. u know those like footie things they have at shoe stores to try on shoes with and theyre usually in a little box and are nude colored? well i took a few home with me when i bought mine and i wear them when i wear my oxfords. it stops blistering because i have a slight layer of protection and they hardly peek out of my shoe!

i’m confused by the opaque tights comment…both pics with stockings show sheer stockings. black, but sheer.

Leave a Comment


OR