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

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• When it was safe to go into the office, I walk 20 blocks to and from work every day, so I'm extremely picky about wearing comfortable shoes.
• I tested each of Everlane's bestselling shoes in my day-to-day life and then ranked them in terms of comfort.
• The Day Glove ($118) is by far the most comfortable, followed by The Day Heel ($145) and The Modern Loafer ($168) once sufficiently broken in.
• Learn more about fit and sizing information for each pair, below.

When it comes to footwear, I am unapologetically picky. A 20-block walk to the office across concrete each day has reduced my tolerance for "cute-but-hurtful" down to nil.

And while Everlane is one of the stores that the Insider Reviews frequents the mosts, its shoes can be hit or miss. The quality is uniformly great, but that doesn't mean the comfort or sizing is. Some styles qualify as our Holy Grail staples, while others are too uncomfortable to wear outside the house. For a brand that's mostly online, this makes committing to a pair of shoes feel high-stakes.

To give you a better idea of how to choose the right size and style for your needs, I tested Everlane's top five bestselling pairs of shoes and reviewed the fit, comfort, and overall experience of each.

But first, some common questions answered:

How do Everlane shoes fit?

Typically, Everlane shoes run small and narrow. I'm a standard 9, but I typically order a half-size up to a 9.5 for Everlane shoes. Most women on Insider Reviews follow this rule of thumb, especially for anything with a pointed toe box, though there are exceptions. If you have wide feet, you may have a hard time finding a perfect fit right off the bat.

Do Everlane shoes stretch?

Yes. The soft leather pairs will stretch and mold to the feet. The stiff leather pairs will, too, but it takes them longer to do so. Everlane's stiff leather shoes require a break-in period or even shoe stretchers, but they will loosen up into a softer and more customized style over time.

What are the best Everlane shoes?

We love the ReKnit Flats ($68), Day Glove ($118), Day Boots ($236), ReKnit Boots ($156), the Rain Boots ($75), and the 40-Hour Work Flats ($118).

For comfort right out of the box, we recommend shopping the company's Day Family collection which is made up of mostly supple, soft leather styles.

Here's my ranking of Everlane's bestselling shoes, starting with the most comfortable and versatile:

1. Day Glove, $118

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 Reviews team's buying guides.

The Day Glove ($118) 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 keep air circulating through the shoes for less stink and sweat (though the difference isn't drastic) and they come in a wide range of beautiful colors.

In the fall, spring, and summer, I wear them about three times per week. They go with everything, are a packable travel shoe, and 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. You should also probably skip them altogether if you need shoes with arch support (or try adding 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 frequently — because you are going to want to throw them on a lot.

2. Day Boot, $236

Everlane's Day Boot ($236) is a versatile, buttery soft bootie that has a walkable 2-inch heel and the kind of soft leather that requires zero break-in time. The insole has even been cushiony enough to support me standing through a full four-hour concert. However, the thin sole makes it easier to scuff the toe, which may be offputting for a $200-plus investment.

With how comfortable and versatile this pair is, it doesn't bother me that you may get less than a few years of pristine wear, though. Mine are scuffed after a year of use, but I still wear them often.

This shoe is one of Everlane's exceptions where you'll want to order your standard size — despite it feeling a little tight initially, I found that it stretched out to the perfect molded-to-your-feet style after the first couple of wears.

3. Day Heel, $145

It's appropriate that the Day Heel ($145) is what put Everlane's footwear on the map. It's inventive, comfortable (even though heels categorically are not), and goes with virtually everything thanks to seven great color options. On any given day, at least one of the Insider Reviews members is probably wearing this heel.

The pull tab makes them easy to slip on, the elastic back lets me 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 own pairs in both a 9 and a 9.5, and I would recommend ordering true to size since the leather stretches with use. The top of the shoe will likely feel tight at points, but over time, I've found that it loosens up. If you need comfortable, everyday heels you can wear to work or on the weekends, these are a great pick.

4. The Modern Loafer, $168

The Modern Loafers ($168) will require break-in time (for me it was a few days 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 walking-heavy activities. I wore comfortable shoes in the morning and switched into these for the workday, breaking them in with short walks around the office.

The loafers run narrow, and I agree with Everlane's suggestion that you should go up a half size. Even with a half size up, I still needed to jam and coax my feet into them for the first few wears, but once they were on, the shoes fit well. 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 probably continue to do so) over time. If you go with a patent leather option, you should go 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 I still ranked them as #4 on this list. The 100% Italian leather is thick and sturdy (hence the need to break them in) but softens with wear, and they offer a slightly more architectural and interesting take on the classic loafer.

But, if you want them, you'll have to act fast — Everlane is phasing them out. We also suggest checking out the Day Loafer for more sizing and color options.

5. The Editor Heel, $100

The Editor Heel ($100) is a beautiful, cooler-than-your-average kitten heel with a low cut vamp that looks sharp, modern, and sleek. 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.

The Editor heels are relatively comfortable — less than the Day Heel and more than other kitten heels I own — but the stiff back gave me 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, 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.

Shop all of Everlane's bestsellers here.