Let’s face it—ordering boots online from a brand you’ve never tried before can feel like rolling the dice. And if you don’t live in the U.S., it’s even trickier.
You’re stuck wondering, Will these fit? or What if I get the size wrong? Trust me, you’re not alone.
Oak Street Bootmakers is no exception. So, how do Oak Street boots actually fit?
In this sizing guide, I’m going to break it all down for you—how Oak Street boots fit in general, how the Trench boots fit, what the official Oak Street size chart says, and how their different lasts affect the fit.
Ready? Let’s dive right in…
Related:
How do Grant Stone typically fit? Here’s everything you need to know about their sizing.
How Do Oak Street Boots Fit?
Key Takeaway:
Oak Street boots fit true to size if you’ve got regular (D width) feet. If you’re wider, size down a half size. Focus on the length, nail the ball-of-the-foot alignment, and let the leather work its magic as it breaks in.
Unfortunately, Oak Street doesn’t offer additional widths at the moment. Their standard sizes online range from Men’s US 7 to 13, but if you need something outside that range—like a size 6 or 14—you can get them as a custom order for certain styles.
Let’s peel back the layers and get into the nitty-gritty…
Oak Street Bootmakers don’t play by the same rules as most boot brands. While Thursday, Grant Stone, and others including Red Wing tell you to size down a half size from your Brannock measurement, Oak Street says, “Nope, go true to size.” That’s right—true to size. This means, if you’re an 11 in your sneakers or dress shoes, you’re likely an 11 in Oak Street boots.
Simple, right?
But (and this is a big but), this advice only applies if you’ve got regular feet—D width, to be exact. If your feet are on the wider side (E or EE), I actually recommend sizing down a half size from your Brannock to accommodate the extra width. So, if you’re an 11.5 in running shoes with wide feet, you’d go down to an 11 in Oak Street boots.
It’s a little counterintuitive, but it works because it helps accommodate the extra width without the boot feeling like a clown shoe.
Oak Street want you to focus less on width and more on getting the length just right. Pay special attention to the ball of your foot—the widest part. It should align perfectly with the widest part of the boot’s last. And don’t forget the heel-to-ball measurement; it’s gotta match up for that “just right” feel.
When you first try them on, expect a snug fit. Not “I need to rip these off immediately” snug, but more like “these are hugging my feet in all the right places” snug.
The leather is premium and will stretch and mold to your feet over time, so that initial snugness is a good thing. It’s like the boots are getting to know you, and honestly, it’s a pretty cool process.
Oh, and if you’ve got narrow feet or just prefer a sleeker, more almond-shaped boot, check out their Lakeshore Boot. It’s designed for a narrower fit, so it’s perfect if you’re after that tailored look.
Related:
Curious how Oak Street boots fit compared to others? While Oak Street runs true to size, Danner boots often fit snugger and may require sizing up for wider feet. Both are great—just different!
Oak Street Boot Size Chart
| Oak Street | US | UK | EU | JP (CM) |
|---|---|---|---|---|
| 6 | 6 | 5.5 | 38 | 24 |
| 6.5 | 6.5 | 6 | 38.5 | 24.5 |
| 7 | 7 | 6.5 | 39 | 25 |
| 7.5 | 7.5 | 7 | 40 | 25.5 |
| 8 | 8 | 7.5 | 41 | 26 |
| 8.5 | 8.5 | 8 | 42 | 26.5 |
| 9 | 9 | 8.5 | 43 | 27 |
| 9.5 | 9.5 | 9 | 43.5 | 27.5 |
| 10 | 10 | 9.5 | 44 | 28 |
| 10.5 | 10.5 | 10 | 44.5 | 28.5 |
| 11 | 11 | 10.5 | 45 | 29 |
| 11.5 | 11.5 | 11 | 45.5 | 29.5 |
| 12 | 12 | 11.5 | 46 | 30 |
| 13 | 13 | 12.5 | 47 | 31 |
Related: Bunny Boot Size Chart and Fit Guide
Now that we’ve covered the basics and the official Oak Street size chart, let’s zero in on how the Oak Street Trench boots fit…
How Oak Street Trench Boots Fit
The Oak Street Trench boots don’t fit like most boots because they’re on the Elston last. The Elston last is designed to be snug in some places and roomy in others—and it works.
So the Trench boots are snug at the heel and slightly loose at the waist, but that’s by design. The addition of a kiltie (that little leather flap under the laces) can help adjust the fit and make the instep and ankle feel less loose and more secure.
The ball of the foot has plenty of room, so there’s no pinching or squeezing, and the round toe shape gives your toes freedom to spread out.
Some people even call it a “duck bill” shape, and yeah, it’s a bit unconventional, but it’s intentional.
When I asked Oak Street why they made an unfashionably round toe, they said your feet swell and get bigger at the end of the day than they are in the morning and that’s why they wanted to make boots that fit you when you come home.
That said, the tRench boot is not exactly true to size—at least not in the traditional sense. If you’re a size 9 on the Brannock, you’d typically go down to an 8.5 in most U.S. boot brands.
But with the Trench boots, if you follow Oak Street’s recommendation to go true size, sticking to your Brannock size might feel too big, especially because of the Elston last’s roomy toe box.
As for width, Oak Street offers the Trench boots in one standard width (D), which works well for most people. But if you’ve got super wide or narrow feet, you might need to get creative with sizing or consider other styles.
In terms of break-in, the Trench boot sis comfortable right out of the box, with no pinching or hot spots. The leather molds to your feet over time, but that initial snugness in the heel and roominess in the toe make them wearable from day one.
So, to sum it up: the Oak Street Trench boots are snug where it counts (heel and waist), roomy where it matters (toe box and ball of the foot), and forgiving enough to accommodate slightly wider feet. They might run a half size large, so consider sizing down if you’re between sizes.
Related:
JK Boots often fit snug, with many recommending sizing down a half size. Here’s everything you need to know about how JK boots should fit.
Now, here’s something really interesting to know…
Old Trench Boots vs. New Trench Boots
Did you know that one of the quirks of the older Trench boots was how your feet would sometimes slide forward, causing your toes to bump against the front when standing still?
It wasn’t a problem while walking, but standing still could feel a little awkward. The issue came down to the design: the sole allowed your foot to slide forward more than it should, and the leather sockliner inside made things a bit too slippery.
It seems Oak Street listened to the feedback and made some smart changes in the newer versions. They removed the leather sockliner entirely and tweaked the last to eliminate the extra space it required.
They also added about a millimeter of toe depth and adjusted the toe spring, bringing it down slightly. The result? A fit that keeps your foot in place, whether you’re standing still or on the move.
Related:
Chelsea boots fit a bit different. They’re designed to hug your feet snugly, especially around the ankle, for that sleek, glove-like feel.
Oak Street Lasts
Oak Street Elston & Lakeshore Lasts
The Elston last is the foundation of some of Oak Street’s most popular boots, including the Trench Boot, Trench Oxford, Trench Chukka, Field Boot, and Campus Chukka.
This last is designed with a wide toe box, making it roomier and more forgiving than some other lasts, like the Lakeshore. If you’ve got regular to slightly wider feet, the Elston last is going to feel like it was made just for you.
Here’s why it works so well: the Elston last is intentionally a bit wider to accommodate the natural swelling your feet experience throughout the day. By the time evening rolls around, your feet have expanded to fill the extra volume, and instead of feeling cramped or desperate to take your boots off, you’re still comfortable. It’s a thoughtful design that prioritizes all-day wearability.
Why did Oak Street design in this way?
The Elston last is intentionally a bit wider to accommodate the natural swelling your feet experience throughout the day. By the time evening rolls around, your feet have expanded to fill the extra volume, and instead of feeling cramped or desperate to take your boots off, you’re still comfortable.
However, if wide-footed people are wearing a pair made with Chromexcel leather, it gets even better. Chromexcel is known for its ability to stretch and mold to your foot over time, so the fit becomes even more personalized and comfortable as you break them in.
But what if you’ve got narrower feet or just prefer a sleeker look? You can go with the Lakeshore last. It’s narrower than the Elston, but thanks to Chromexcel’s stretch, it can still accommodate a bit of width over time.
Let’s talk about hand lasting—a method Oak Street Bootmakers takes seriously and uses for all their Goodyear-welted boots.
Related:
Thinking about hitting the trails? Hiking boots are designed to fit snug around the heel for stability while giving your toes room to move. Here’s everything you need to know about how hiking boots should fit.
Other Lasts:
5504 Last: Designed for laceless boots, this last has a round-but-narrow toe, a flat heel, and a sharply contoured vamp. The result? A secure, snug fit that keeps your foot in place without the need for laces.
800 Last: With its gently rounded toe, it’s built for all-day comfort, making it perfect for loafers you can wear from morning to night.
555 Last: A classic New England moccasin last, the 555 offers a medium width and a broad toe.
304 Last: It has a similar silhouette to the classic moccasin 555 last but with a slightly more athletic shape. This gives you a more secure, true-to-size fit.
Related:
RM Williams sizing works a bit differently. Curious how they compare? Check out our guide on how RM Williams sizing works and how they fit to see which brand might be your perfect match.
Oak Street Hand Lasting
Unlike machine lasting, where the process is automated and consistent, hand lasting allows for a more nuanced approach.
Each piece of leather is unique, and hand lasting gives the craftsmen the ability to adjust the tension and pressure as they pull the leather over the last. This means they can account for variations in the leather’s thickness, stretch, and grain to ensure a better fit and finish.
As Oak Street puts it, “The reason we chose to go with hand lasting is because you can dial it in much better by hand. Every piece of leather stretches differently, and you can’t achieve that level of precision with a machine.”
This hands-on approach might mean the pressure isn’t as firm or consistent as a machine’s, but that’s not necessarily a bad thing. It allows for a more organic, tailored result that complements the natural characteristics of the leather.
Plus, hand lasting reduces the risk of overstretching or uneven tension. So, while machine lasting might be faster, hand lasting is more labor-intensive process, but it’s one that reflects Oak Street’s commitment to quality and craftsmanship.
Related:
Curious how Oak Street boots compare to other footwear? Check out our guide on how Xtratuf boots fit to see how their sizing and design stack up.
The Best Way to Know if a Boot Fits
Let’s be honest—nothing beats trying on the exact model you want in a store. You can feel the fit, test the comfort, and walk around the boots to make sure they’re right for you. If you can, always go this route.
But if online shopping is your only option, don’t stress. Use the tips below to measure your feet accurately. And remember, most reputable brands have hassle-free return policies, so you can exchange them if needed.
How to Measure Your Feet
In the Store
A trained professional can measure your feet using a Brannock device, which gives you the most accurate length, width, and arch length measurements. They’ll also assess how your feet sit on the device and recommend the best size for your foot shape. If you have the chance to visit a store, this is hands-down the best way to know your size.
If you’ve got access to a Brannock device but no professional to help, don’t worry—you can still get a good measurement…
At Home
Stand on the device, align your heel with the back, and check where your longest toe lands. Don’t forget to measure the width by sliding the bar to the widest part of your foot.
Pro tip: Measure both feet and go with the larger size if there’s a difference.
If you don’t have access to a Brannock device, you can find printable versions. Print it out (make sure it’s scaled correctly), place your foot on the chart, and mark where your heel and longest toe land.
Measure the distance between the marks and compare it to the size guide. It’s not as precise as the real thing, but it’s a solid DIY option.
Here’s a video showing how to use the Brannock correctly…
Without a Brannock
If you don’t have a Brannock device or a printable chart, you can still measure your feet. Grab a piece of paper, a pen, and a ruler. Stand on the paper, trace your foot, and measure the length from heel to toe.
Compare this to the brand’s size chart. For width, measure the widest part of your foot and check the brand’s width guidelines.
Important Tips for a Perfect Fit
- Measure at the end of the day: Your feet swell throughout the day, so measuring in the evening ensures a more accurate size.
- Wear the right socks: Measure with the socks you plan to wear with the boots. Thick socks can add half a size!
- Check the ball of your foot: The widest part of your foot should align with the widest part of the boot.
- Leave some room: There should be about a thumb’s width of space between your longest toe and the end of the boot.
- Walk around: If you’re trying boots on, walk around to see if they pinch, slide, or feel uncomfortable.
Wrap Up
So, there you have it—everything you need to know about how Oak Street boots fit. From the roomy Elston last to the sleek Lakeshore last, and from the Trench boots to their other styles, we’ve covered the ins and outs of sizing, lasts, and what to expect when you slip them on for the first time.
Ordering boots online can feel like a leap of faith, but with a little guidance, you can nail the fit and avoid the hassle of returns.
Remember, it’s all about understanding your foot shape, paying attention to the details, and being prepared to tweak your size if needed.
Now, I want to hear from you! Have you tried Oak Street boots? How did they fit for you? Drop a comment below and share your experience—it might just help someone else figure out their perfect size.