Reader Question: What To Wear With Oxfords?


Reader Question:

I love love love your web site. It's incredibly well written, topical, helpful, inspirational, practical… the accolades go on. My husband is a little worried because I've been reading it obsessively since I came across it a few weeks ago after Googling "wearing flats with flares" and found your post with that almost exact same title (BTW, after reading your article I bought a pair of Banana Republic flares to try out the style — waiting for them to come back from the tailor. I lost quite a bit of the flare by shortening them so much bu
t I think they're going to look great).

Screen Shot 2011-09-24 at 5.53.04 PM My question: I bought this pair of lace up oxfords from Madewell last spring and I'm not sure what to wear them with. I don't wear a lot of flowy/girly type dresses — I prefer tailored (I'd say 75% of my wardrobe comes from J. Crew) and more body conscious (despite remaining pooch 5-years post — the rest of me is in good shape, I swear!). I also am extremely conscious of dressing age-appropriate. They are super comfortable and super cute so I'd like to make them work with a few options. Any ideas?



– Jodi



Jodi – thank you for your incredibly kind email!  You made my day.  And your oxfords are fabulous.  Oxfords are one of my new favorite styles….so geeky chic, but in the best possible way.  They do look adorable with girly, flowy dresses (love the juxtaposition there), but they can also look ah-mazing with some mom-friendly separates as well.

Try them with a short little dress…

You mentioned that you were in good shape (you lucky ducky)….so if I were you, I'd be dying to rock these shoes with a dress that is slightly body conscious, like J.Crew's Sightseer Dress.  Alternatively, you could try a little plaid dress that walks the line between girly and tailored, like the one below from Dear Creatures.  




Pull this look together with a cool jacket, a cross-body bag and your oxfords.  You could even wear little socks, if so inclined. (And this would be a great look for your upcoming trip to Italy, mentioned later in your email…)


If Denim is your thing….

Cool shoes always work with a rolled jean to show them off.  And the blazer + boyfriend jean + tee combo is a perfect foil to show off shoes and jewelry.  This is geek chic at it's best:  easy, comfy and cute.  Again, adding socks is an option here.





Of course there's always shorts….

Yup, denim shorts.  Yup, they were part of my Summer mom-uniform/ mom-i-form, and yup – they are now making a strong showing in my Fall mom-i-form.  





Tailored shorts would be equally cute here, as would a skirt…but you guys know how I feel about my denim cut-offs.  We're like THIS (picture my fingers entwined).

Jodi, I think these shoes were a great purchase.  Don't be afraid to roll your pants to show them off, and experiment with some larger silhouettes (over-sized sweater, boyfriend jeans) to prevent the whole skinny-girl-in-clunky-shoes look.

Mamas, I haven't taken the oxford plunge yet, but now I'm seriously tempted.  How are you guys wearing yours?  Link up below if you have any oxford pics!!  Us Mamas need all of the inspiration we can get!



Best_mom_fashion_blogOh, and hey!  Please don't forget to take a sec to vote for Ain't No Mom Jeans for's Best Mom Fashion Blog award–we'd love it!  Just click the pic : ) xoxox




  1. I’ve been looking and looking and looking for some flat oxfords, and the ‘perfect’ pair just hasn’t showed up yet…but I wear my heeled ones constantly!
    I think your ideas are just awesome, S, especially the reminder to roll the pants. Of course, my thought always runs to a maxi skirt (surprise, right?). They’d look so cute peeping out from the hem, and a great black maxi is so versatile for cool weather.

  2. Thanks! This is great. Let me just clarify the shape comment… Its not so much a skinny thing. I have a very athletic frame and tend to look like a line backer in certain over-sized styles but you’ve given me some great ideas. awesome.

  3. Sad fact: I tried to purchase some oxfords months ago, but I was so overwhelmed by the number of cute choices on Modcloth that I ended up with none. Maybe I’ll check back and see they’ve been marked down. Here’s hoping!

  4. Thanks for the ideas, I have a pair of grey oxfords but haven’t taken them out of the box yet as I wasn’t quite sure how to wear them. Maybe I’ll wear them tomorrow

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