I put 5 of Everlane's best-selling shoes to the test in NYC - and ranked them by comfort level

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I am insufferably picky about footwear. I have a 20-block walk to and from work over hard concrete, and I'm cursed with a love of things that look cooler than they are meant to be comfortable. In the end, I owe it to a job that requires me to spend the lion's share of my time testing bad, good, and amazing products that I've found anything that ticks both boxes at all.

Everlane has exceptional footwear in terms of quality and price in general - though we at Insider Picks will be the first to say it also varies drastically in sizing and in comfort. Some shoes are so narrow you'll find yourself sizing up two full sizes, and others feel like they were sewn using your foot's exact dimensions as the pattern.

For a store that's mostly online, it can be a high-stakes guessing game.

To give you a better idea of what to expect before you buy, I ranked five best-selling shoes at Everlane to see what the pros and cons of each are.

If you want a simple rule of thumb you can't go wrong with, shop from the company's Day Family collection. Beyond that, order a half size up across the board if you're unsure and make sure you don't forget to remove the transparent liner on the bottom of every shoe - the soles will slip if you don't.

Here's my final ranking, starting with the best:

1. Day Glove, $115

In the unlikely instance that a cocktail party includes the icebreaker "If you could only buy one pair of flats for the rest of your life, which pair would it be?" (maybe it's a very specific kind of event) I have my answer locked and loaded: The Day Glove. These shoes are the consummate flat, and they're wonderful from the minute you take them out of the box. They were also voted the #1 best flats you can buy in the Insider Picks buying guides.

The Day Glove ($115) requires zero break-in time, the premium leather is soft, supple, and molds to your foot for an increasingly customized fit over time, and the elongated upper negates both angry red lines and the feeling that you may slip out when taking a deep step. The perforations on the side are meant to keep air circulating through the shoes (for less stink and sweat) and they come in a wide range of beautiful colors.

Since getting them a few months ago, I've averaged wearing them about three times every week. They go with everything, are a packable travel shoe, and they handle the 40-block round-trip walk without a problem.

Having said that, you should order a half size up (I wear a 9.5 in these, and a 9 typically), and you shouldn't buy them if you need arch support in your shoes (or you should add some insoles).

If you only plan to buy one pair - they're $115, after all - my advice would be to invest in a classic color like black or white that you can wear as frequently as you want - because you are going to want to, very frequently.

2. Day Heel, $150

The Day Heel ($150) comes second only due to the Day Glove's excellence, rather than any failing on the Heel's part.

It's appropriate that this is the shoe that put Everlane's footwear on the map. It's inventive, comfortable even though heels categorically are not, and goes with virtually everything thanks to 11 great color options. On any given day, at least one of the Insider Picks teammates is probably wearing this heel.

The pull tab makes them easy to slip on, the elastic back means I can wear them all day without the threat of throbbing or blisters, and the cushiony insole adequately protects me from the constant slam of my feet against city pavement. Also, they mean it when they say the low 2-inch block heel is walkable - these work painlessly on my 40-block walk, and they don't slow me down.

I have a 9 (true size) and a 9.5, and after the leather has stretched comfortably with use, I would recommend sticking true to size for these unless you are extremely uncomfortable. The top of the shoe will likely feel tight at points, but this has loosened over time. If you need comfortable, everyday heels you can wear to work or on the weekends, these are a great pick.

3. The Modern Loafer, $165

These loafers will require break-in time (a few days for me of consistent wear), and you will feel it in your heels. For at least the first handful of times you wear them, you won't want to rely on this pair for long walks or walking-heavy activities. For me, I broke my default rule and wore comfortable shoes in the morning and switched into these for the work day, breaking them in with short walks around the office.

The loafers run narrow and I agree with Everlane's suggestion that you should size up a half size. Even in the half size up, I still needed to jam and coax my feet into them for the first few wears. But, once inside, the shoes fit ideally. If you have plans to wear them with socks, though, I'd suggest going a whole size up - at 9.5, they're snug on me, though they have loosened (and will likely continue to) over time. If you go with a patent leather option, you should start by going up a full size since it won't stretch the same way as other leathers.

All in all, though, The Modern Loafer is a great shoe if you can pay the initial painful debt of breaking them in - which is why they still rank as #3. The 100% Italian leather is thick and sturdy (hence the breaking in) but soft with wear, and with 10 color options, you can opt for a classic or statement pair easily. They go with everything, won't be going out of style any time soon, and nail the elegance and polished aesthetic of loafers with the bonus of an added architectural component that makes them slightly more interesting.

4. The Modern Oxford, $168

All in all, I absolutely love these shoes - probably as much if not more than any other pair on this list - but their break-in period and sizing make them a tough pair to work with initially, which is why I've ranked them #4.

Having said that, these shoes are cool. If you like elegant, edgy, or effortlessly self-assured, you will love the way these look on.

I've mentioned that the Modern Loafers require a break-in period, but these require a more intense one. While the loafer shape allows you to bend out of the shoes themselves intermittently, that's not the case for Oxfords that you're laced into, and which are made from a stiffer leather. There's nowhere for your foot to slip out and escape to in these, and, as a result, the friction is more intense. Do not try to break these in without socks on unless you are a masochist. But, with socks (and maybe some proactive band-aids applied) you should be fine, and they'll feel custom-made after eight or more wears.

I typically wear a 9, and Everlane suggests sizing up if you're in between sizes. I've tried both the 10 and 9.5, and the 9.5 is perfect. The narrow fit keeps them looking suave and elongated, and they're the kind of shoe that encourages you to take up space without apologizing for it. If you like masculine elegance, you're probably going to love these - and for their specific look, quality, and price, they're worth the painful break-in period.

And, like all Everlane shoes, be sure to remove the transparent liner from the bottom before you wear them - you'll need to scuff up the soles before they stop feeling a little slippery.

5. The Editor Heel, $165

The Editor Heel is a beautiful, cooler-than-your-average kitten heel with a low cut vamp that looks sharp, modern, and architectural. It has Everlane's go-to pull tab on the back for ease, a walkable 2-inch heel, and is made out of 100% Italian suede. Overall, these things are sleek.

The Editor heels are relatively comfortable - less than the Day Heel with its elastic back and more than other kitten heels I own - but the stiff back could give you blisters with extended wear. Everlane says the Editor heels run big and to size down if you're in between sizes, but I'm glad I stuck to my true size - even there I noticed some tightness in the narrow toe box, something that will hopefully loosen after many wears. If you followed Everlane's instructions for a smaller size, though, and you could fight through the break-in period, you'd probably wind up with the perfect fit one day. To me, though, it's just not worth the pain.

It's also worth noting that while these heels are pretty comfortable in my mind, you probably won't want to be in them all day. For that tall order, buy the Day Heel (or the Day High Heel for a higher heel).

Shop Everlane's best-sellers on your own here >>