How to wear Oxfords? (And a happy ‘first!’)

I’m a shameless complimenter. If I like something a stranger is wearing, I always make a point of saying so. In a restaurant? Sure. Elevator? Why not? Walking across campus? Always. Even if I’m on the phone? Yup.

I’ve been doing it for years, but I’ve never been complimented by a stranger before. Last week, it finally happened! I was walking across our campus quad, and a girl broke off her phone conversation to tell me she liked my outfit. It completely made my day — it was nice to be on the other end of something I always do.

So, the outfit. I bought a pair of Oxfords a few weeks ago, partially because I needed flat-yet-formal shoes to run around in while reporting but mostly just because I wanted a pair. Unfortunately, I did what I always do: I bought a “trendy” item, then got home and realized I had no idea how to wear it. I turned to the internet for help and came up with the outfit below.

Most of the “How to wear Oxfords” articles I read said to wear them with “feminine clothing,” to balance the menswear feel of the shoes. Doesn’t get any more feminine than a dress, right? I added a floral necklace, too, and tights for warmth. I really liked the end result — it was super comfortable, and I didn’t think it strayed too far from my usual look. I test-drove the outfit while I was home on winter break, hence the “in-my-backyard” photo, and wore it on campus for the first time last week. I’ll definitely wear this again.

Last night, I broke out the Oxfords again for a party. I was really tired of wearing jeans and boots everywhere, but it was too cold and raining for a skirt and bare legs, so I went a little crazy and tried to put together a shorts-and-tights outfit for the first time.

I had to send a picture to my sister before I actually wore this out in public (“Is this an outfit?”),  but she approved, and I was decently happy with it as well. I’d go with a fitted t-shirt in the future — this one was essential to the party’s theme — but the concept works. It was great to wear, too — I felt like I was dressed up enough to be at a party, but it was super comfortable, too.

Do you wear Oxfords? I put these outfits together, but I still mostly have no idea what to do. Let me know how you wear yours! Cheers.

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