When October arrives in Monsey, NY, where Laced Shoe is based, boys start wearing their wingtip booties as the weather cools. Parents seek styles that not only keep feet warm and comfortable but also ensure boys look sharp for both school and Shabbos. The classic yet modern wingtip booties meet these needs effectively, making them a popular choice as the fall season begins.
Why the Wingtip Bootie Design Is a Favorite
The wingtip design mixes classic style with a modern touch, making it great for both dressy and casual days.
Some wingtip boot styles have a wood trim around the sole that leans into that rugged vibe, while others have a slim black sole that reads very classic and preppy. Either way, the detailing makes them look like little gentlemen and gives a timeless, elegant feel that parents love in photos.
Lace-Up vs Slip-On Wingtip Booties
Both lace-up and slip-on wingtip booties feel timeless and polished. The lace-up wingtip for kids usually has a side zipper, which gives you that adjustable lace fit with the easy on and off that busy mornings need.
The slip-on wingtip does not have that same adjustability, so the foot can move around more if the fit is not perfect. For kids with trickier feet or in between sizes, parents often appreciate the control they get from laces plus a zipper.
Quick fit takeaway:
- Lace-up + zipper: more adjustability and a more secure fit for tricky feet or in-between sizes.
- Slip-on: faster on/off, but needs the fit to be just right so the foot doesn’t move around.
Helpful links: Kids Shoe Size Guide and How to Measure Kids’ Feet.
Ready to shop the look? Shop Boys Wingtip Booties now to ensure the perfect fit before it's gone. Our most popular sizes often sell out by mid-October, so act quickly to avoid missing out.
How to Style Boys' Wingtip Booties for Events
For a dressy event, pair boys' dark brown or black wingtip booties with slim dress pants, a crisp button-down shirt, and a sweater or blazer on top. Keep the pants tailored at the ankle so the booties show, and match the leather tone to his belt or kippah so the whole outfit feels pulled together.
For slightly more casual events, wingtip booties look great with dark chinos and a knit polo or fine-gauge sweater. Choose neutral socks that blend with the pants and make sure he can walk and run comfortably, so he looks sharp in photos but can still be a kid.
Easy outfit formulas:
- Dressy: dark brown or black wingtip booties + slim dress pants + button-down + sweater/blazer
- More casual: wingtip booties + dark chinos + knit polo or fine gauge sweater
- Finishing touches: tailored ankle length, neutral socks, match the leather tone to the belt or kippah.
Explore more: Boys Boots or Boys Winter Boots.
Are Wingtip Booties Good for Special Occasions?
Wingtip booties give a polished look, which makes them perfect for special occasions and holidays. They have that mini gentleman vibe that parents love for school photos, family pictures, and big milestones.
They are a popular choice for school photos, family events, weddings, Bar Mitzvahs, and church, because they dress up pants instantly without feeling like stiff “church only” shoes. According to The Laced Shoe, these booties are designed for comfort and durability, so kids can wear them at special occasions and still enjoy them for everyday use.
Need help choosing the right pair? Book a fitting or shop the collection.
Must-Have Wingtip Booties at Laced Shoe
Our classic boys wingtip bootie is from Manuela De Juan, style S2369, and it is a style we bring in year after year. We change it up with different colors and shades each season, but parents keep coming back because it is consistently comfortable and sharp-looking.
For younger kids, a must-have is the Emel slip-on wingtip bootie, style 2733. It is geared more towards little ones who are on the move and need something soft, sturdy, and easy for parents to slip on quickly.
- Manuela De Juan S2369
- Emel 2733
Manuela De Juan S2369 vs Emel 2733
The Manuela De Juan S2369 bootie looks narrow and refined with its slim profile and side zipper, but it actually works for most foot types, from narrow to wide, when sized correctly. It is a great option for dressy outfits that still need everyday comfort.
The Emel wingtip slip-on bootie is wider all around, so kids with wide feet feel very comfortable in these. The Emel bootie also features a sturdier sole, making it ideal for everyday activities, walking to school, and long days on their feet.
At a glance:
- Manuela De Juan S2369: narrow, refined look + side zipper; works for many foot types when sized correctly
- Emel 2733: wider fit + sturdier sole; great for everyday and long days on their feet
Fit and Comfort Notes
Both of these boys' wingtip booties are all-day friendly, but they shine in different moments. For long Shabbos walks or a full simcha where your boy is on his feet for hours, the Emel slip-on wingtip with its sturdier sole is amazing, offering more room and support. For school, Yom Tov outfits, and any time you want that narrow, refined look that still feels soft and flexible, the Manuela De Juan style S2369 is the pair you will keep reaching for. Comfortable Shoes
Are These Styles Always in Stock?
These are classic styles for us, but we still like to change things up each year so the collection feels fresh. The brown leather will usually be a few shades different from season to season, and we may add a black leather wingtip with a more textured finish to add a new element while keeping the same trusted fit.
FAQ: Boys Wingtip Booties
When do boys start wearing booties?
Once October hits in Monsey, NY, boys start wearing booties because the weather cools down, and parents want something warmer that still looks sharp for school and Shabbos.
What’s better: lace-up or slip-on wingtip booties?
Lace-up (usually with a side zipper) gives more adjustability and a more secure fit. Slip-on is faster, but it needs the fit to be just right so the foot doesn’t move around.
Are wingtip booties good for special occasions?
Yes—wingtip booties are polished and popular for school photos, family events, weddings, Bar Mitzvahs, and church, because they dress up pants without feeling like stiff “church only” shoes.
How do I measure my child’s foot for the right fit?
Use our quick Shoe Guide to measure from heel to toe while your child stands. Compare the length to our size chart—when in doubt, size up for growing feet.
How do I clean and care for laced shoes like wingtip booties?
Wipe with a damp cloth and mild soap. Let them air-dry and avoid harsh cleaners. For leather-laced styles, a light conditioner helps keep them looking new.
What if the size or color I want is sold out?
You can sign up for restock alerts on the product page, and we’ll notify you as soon as it’s available again.
What if the shoes don’t fit?
You can return or exchange unworn shoes within our standard return window. Check our Shoe Guide for fit tips before sending them back.
If you are ready for that mini gentleman look, now is the time to grab his wingtip booties. Shop our boys wingtip bootie collection online or stop into Laced Shoe in Monsey or Lakewood for a proper fitting and help choosing the best style for his feet.