Brooks Brothers Chukka Boots – $314.30 ($449)
About the Author: Adam Terry is a thirtysomething business analyst in the construction industry. He enjoys whiskey, watches, boots/shoes, and working on his dad bod father figure.
Few footwear styles bridge the gap between casual and formal as elegantly as the chukka boot. These ankle-high classics have graced everything from neatly pressed suits to well-worn denim, becoming a cornerstone of the dapper man’s wardrobe. Brooks Brothers’ latest entry into this category promises to fill that go-anywhere role with a sleek design that seems to be good enough to wear everywhere – a modern boardroom or a casual brunch. However, in a market saturated with exceptional offerings, looking the part isn’t enough (especially at this price point). Let’s explore whether these boots deliver substance to match their velvety style.
Available in brown suede or a textured black leather.
The Adam Review Scale of Excellence (A.R.S.E.)
- 5 – Outstanding! Very nice and well worth the price of admission. Highly recommended.
- 4 – Very satisfactory. Above average, may have very minor issues but still worth it.
- 3 – Satisfactory. Average at best. May have notable issues, may be OK for some at this price.
- 2 – Unsatisfactory. Below average due to defects, flaws, or other imperfections.
- 1 – Poor. Significant issues, not worth purchasing at any price. Avoid!
Details
- Brand: Brooks Brothers
- Style: Two-eyelet Chukka Boots
- Size: 10.5 D
- Last: N/A
- Construction: Possibly Blake stitched
- Upper: Suede
- Sole: Vibram Dainite-like studded sole
- Details: Blind metal eyelets
- Extras: Twill cloth shoe storage bags
- Country of Origin: China
- Price: $449 US
Versatile chukka shape.
Ordering/Delivery/Returns
This pair of chukkas was ordered on a Monday morning (post coffee run, naturally) from the BB website. They shipped out the next day from a warehouse in Hartford, CT and hit the road via UPS Ground service. This package was delivered that Friday afternoon. Brooks offers free standard shipping on all orders $200 and up, but if you’re a Brooks Brothers Rewards member and achieve VIP status, you’ll receive complimentary standard shipping on all orders.
FYI: Standard returns have a 60-day window from the date of purchase to be returned for a full refund minus a $7.00 return fee. However, the Brooks temporary extended holiday return policy allows for orders made from October 1st through December 31st to be returned until January 31st. Some exclusions apply, such as items that are 70% off or items marked as final sale.
Score: 5/5 Stars – Easy online ordering, fast and trackable shipping. Simple returns.
Classic American Brand. Chukkas are made in China.
(Which is hardly unusual in the retail world.)
Packaging/Unboxing
This pair arrived in a sophisticated navy blue shoe box with gold foil Brooks Brothers branding on the lid that evokes a touch of class and the potential for high quality goods that might await. Inside, each shoe was individually wrapped in a plastic bag, nestled within layers of tissue paper, and stuffed with a hardened paper form to maintain its shape during transit. Brooks also bestows upon us a pair of twill fabric shoe storage bags that have a texture more similar to an unlined cotton sport coat instead of the typical flannel cotton cloth that we usually see.
Overall, this above average unboxing experience was a cut above more budget-friendly brands like Banana Republic or J.Crew. The packaging suggests a thoughtful approach to the product presentation and some product care, which is always nice, but for the price, it was not quite as luxurious as higher tier shoemakers like Grant Stone, Allen Edmonds, Alden, etc.
Score: 4/5 Stars – Unboxing experience was above average, but could be better.
Comes with twill (not flannel) shoe bags, inside a nice box.
First Impressions
Fresh out of the box, these chukkas immediately impress with their rich chocolate brown suede uppers, presenting an incredibly versatile silhouette that seems to effortlessly navigate the highly nuanced crevice between “smart” business casual and the less formal office casual dress codes. The rich, velvety suede has a depth of color and texture that simultaneously evokes classic menswear heritage and modern sartorial sensibility. While I can’t speak to the source of this suede (and the CS rep at Brooks Brothers couldn’t either when we asked), I can say with certainty that this hide feels nice and seems to be on par with similar suedes from C.F. Stead.
Rich chocolate brown suede.
Shape navigates between “smart” business casual and less formal office casual.
The two-eyelet upper design is a masterclass in minimalist elegance, providing just enough shape and structure to define the boot’s silhouette while maintaining a clean, uncluttered aesthetic. The toe box is slightly rounded and has a subtle elevation, adding to this boot’s look. The round waxed cotton laces add a subtle tactile dimension, too, as their slightly waxy sheen catches the light and provides a textural contrast to the soft suede. Blind metal eyelets are meticulously integrated into the upper, creating smooth lines that enhance the boot’s refined profile—each eyelet is subtly recessed and helps maintain the sleek, uninterrupted surface.
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Internally, the full leather lining offers a premium feel against the foot, with the tan calf leather promising both comfort and durability over less expensive fabrics or cheaper suedes. The leather half sockliner extended from the heel to the midfoot; underneath, there are two thin foam layers separated by a layer of paper or paperboard. This sockliner assembly is glued down to a fiberboard lasting board, which is then dovetailed into a “100% leather” stamped front piece. There appears to be stitching around the front, which suggests some level of Blake stitching, but these lines do not go beyond the midfoot.
Leather lined. Two layers of some foam cushioning.
I believe these boots are simply Blake stitched up front to the lasting board and then glued around back (or the stitching is hiding). This hybrid construction might ensure some structural integrity while maintaining the boot’s streamlined shape, but the discreet fake welt and mis-matched welt to outsole stitching gives it away – these boots are barely stitched at all. Unfortunately, that would mean these boots would not have the traditional resoling capabilities of a typical Blake or Goodyear welt, but this design does provide a clean visual finish that aligns with the boot’s contemporary design.
Possible hybrid construction with Blake stitched up front and cemented in the rear.
Perhaps the most interesting bits are the Vibram XL Trek studded rubber outsoles, which transform these chukkas from a purely aesthetic piece to a genuinely versatile footwear option. The studded rubber design mimics the well-known Dainite soles that provide exceptional traction and durability, but the Vibram version is made from lighter (and less durable) rubber. That makes these boots suitable for varied urban environments while maintaining their style-forward approach, but with the caveat that the outsoles and heels may wear out faster.
Score: 3/5 Stars – Looks are killer, but the materials are not up to par for this price point.
Vibram XL Trek studded rubber outsoles are lighter (and less durable) than Dainite.
Sizing/Fit/Comfort
In terms of fit and sizing, I recommend trying a half-size up from your true-to-size Brannock measurement. I tried this pair in my usual 10.5 D and they feel a touch too small in both length and width. Sizing up to an 11 D would probably solve this fit issue and shouldn’t be too much room as to cause any heel slippage or loose feeling around the ball of the foot. Note that this pair is only offered in a standard D width and the size range/run is rather limited.
For size reference, I consider myself a 10.5 D on a Brannock device (10.5 heel to ball, 11 heel to toe with high arches). For roomier lasts like Alden’s Barrie or Grant Stone’s Leo, I take a half-size down to 10 D. For “true to size” lasts, like Allen Edmond’s 65 last, I tend to go TTS with a 10.5 D. For sneakers, I prefer a 10.5 with Converse and an 11 with Nike, Adidas, etc.
Slipping on the Brooks Brothers chukkas reveals a nuanced first impression of comfort and construction. The tan calf leather lining provides a smooth, comfortable interior that feels nice against the foot, while the leather-topped half sockliner offers a pleasant, cushioned initial step with strategic foam layering underneath—notably around the heel and midfoot—which provides appreciable shock absorption and some added comfort. However, these foam layers are on the thin side. The forefoot’s thinner leather layer is less comfortable out of the box than others. Overall, this design balances some initial structured support with a notable cost-savings approach. The combination of materials creates an interesting tactile experience: plush and well-padded in some areas, more streamlined, firm, and traditional in others.
Score: 3/5 Stars – Sizing runs small, so size up accordingly. Initial comfort is OK.
Runs half a size small. Only available in standard D widths.
Final Thoughts
Beneath the storied Brooks Brothers name lies this peculiar misstep in their footwear lineup. These chocolate brown suede chukkas, while handsome at first glance with their studded Vibram soles and clean/conservative silhouette, occupy an awkward space in the premium boot market. At $450, these boots force you to question whether you’re paying for the prestigious label rather than the craftsmanship itself. While the rich suede upper catches the eye and promises boardroom-to-weekend versatility, the (allegedly) Blake stitched construction and thinner materials make this package fall short of what you might expect at this price point, especially when companies like Allen Edmonds and Grant Stone are crafting superior products with higher quality materials and Goodyear welted construction at more attractive prices.
Overall, I rate these chukkas slightly above average and potentially worth it when they drop in price below ~$300 US. If these were made with better materials and better welted construction, I could justify the full retail price point because these boots look incredible from afar. Cheers!
Avg. Score: 3.75/5 – Style over substance here. Overall, these look great when on sale.
