sphinx consult: shoe dilemma


Dear Sphinx,

I hope this letter finds you well. I have been enjoying your recent blog posts and came across a purchasing conundrum. I am torn between two shoes:


Eastland Women’s Open Road Slip On


Eastland Women’s Double Up Jodhpur Boot

[vendor images]

I have purchased both in black leather and would love your opinion on the matter as I appreciate your good taste.


1. I own four pairs of ankle boots- classic chocolate brown Timberlands for heavy duty snow; Timberland Victorian-styled in sand, Naturalizer Onset in an olive color with chunky low heels; and Clarks Vermont Stowe in dark brown, the dressiest pair. I don’t own any dress shoes that resemble the slip-ons.

2. I am considering these shoes mainly for work purposes as I need something professional but wearable standing for long hours. I work in a lab in which heels would be impractical but there is still a business casual dress code. Instead of going for flats I want a lot of foot coverage in case of nasty spills.

3. Most of my dress pants (which I will be wearing, skirts rarely) cover so much of these two shoes that the silhouette is virtually indistinguishable from each other. I do like the detailing that peeks through with the buckled shoe, as well as how it leans towards a menswear shape (it looks great with skinny jeans too). They are both comfortable though there is a little more heel slip associated with the boots that is expected (despite being a half size smaller). I am a little worried about the leather stretching out but its nothing that can’t be fixed by wearing thicker socks.

I guess my dilemma right now comes down to whether I need another pair of ankle boots (albeit different look and color) or if it would make more stylistic (and financial) sense to opt for the buckles. I think I can wear both casually outside of work, which makes the decision harder.

Keep both? I am trying not to, so am needing a fresh perspective.

Hope to hear from (and hopefully not bore) you,

Lab Rat


Dear Lab Rat,

I am happy to weigh in, and enjoy playing the role of stylist/consultant!

To me the silhouette of the ankle boots is close enough to the Clarks and the Naturalizers to make me lean toward the slip ons, with the larger goal of adding diversity to your options in mind. I’m wondering: if you were to give yourself the task of finding a new pair of flat ankle boots (outside the task of finding work shoes), are these the ones you would choose? Or, on the other hand, if you were to give yourself the task of finding a new pair of menswear-esque high coverage flats, are these the ones you would choose? [Imagine the universe of oxford flats and loafers out there] Then, if you are interested in getting a (more appealing) pair in one of these categories in the future, maybe better to get the other category now. Hard to say, sometimes. Some people are happiest with a bunch of what is virtually the same shoe.

Usually if I am not certain of a choice I like to postpone, and keep browsing (or buy it/try it on). Uncertainty, at least for me, often means that I have one too many reservations about an item, and that I am sure to find something I like more with time. Once I find a few more alternatives (whether I like them slightly more or slightly less) it makes the final decision easier, and it makes me more confident about my choice. I think you should like them a lot. I would assess them for quality as well, durability, niceness of the leather, quality of the stitching, etc. Sometimes when people wonder if they should keep both of something, it would be just as satisfying not to keep either. When you really want something, you tend to know. [At least, when I really want something, I tend to know.] I can’t tell if that is at all helpful or not!

Good luck!