Best Men's Dress Boots (Sep. 2026) - Rated by CherryPicks' Experts

At a Glance: Our Top Picks

Top 1

Bruno Marc Men's Dress Ankle Boots Cap Toe Lace-up Oxford Boot Black Size 11 ...

9.8
CPR Score
Top 2

Bruno Marc Men's Mid Top Chukka Sneaker Dress Boot,Black,12

9.8
CPR Score
Top 3

Lee | Waylon Chukka Boot for Men | Durable & Stylish Mens Chukka Boot | Every...

9.7
CPR Score
Tips


Our team has recommended top 27 Men's Dress Boots to make your shopping easy after considering different features about Men's Dress Boots reviews of brands, including Amazon Essentials, Lee, Clarks, Deer Stags, Vostey, Nunn Bush, Thursday Boot Company And Arkbird. And after researching, Bruno Marc Men's Dress Ankle Boots Cap Toe Lace... is a highly recommended Men's Dress Boots item.

* CherryPicks.Reviews is reader-supported, Our editor review, and recommend the best products based on extensive data analysis, if you click on the product links, we may earn a commission through qualifying products purchased.

The Best Men's Dress Boots Rated by CherryPicks

Market Overview
Men's Dress Boots Reviewed
  • Reviews Analyzed: 112,308 Items
  • CPR Avg. Rating: 8.6 / 10
27 Products Evaluated
  • Highest Price: $199.00
  • Lowest Price: $17.54
  • Avg. Price: $48.17
Price Disclaimer

Top 27 Men's Dress Boots on Amazon (Verified You can Buy)

Bruno Marc Men's Dress Ankle Boots Cap Toe Lace-up Oxford Boot Black Size 11 M US Warner-2

Bruno Marc
B205-2C5AM03-G12MJ-PF112P

Ratings for Bruno Marc (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
topshoesUS 88

Features

Premium synthetic leather for breathability
Cushioned footbed for shock-absorption
Show More

Bruno Marc Men's Mid Top Chukka Sneaker Dress Boot,Black,12

Bruno Marc
B205-2C5AH02-G12MK-PFEK

Ratings for Bruno Marc (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
topshoesUS 88

Features

Stay Dry Anywhere: Water-resistant PU leather upper ensures protection against splashes during daily casual wear or outdoor activities, making these men's boots reliable for versatile scenarios.
Keep Feet Cool: Breathable fabric lining prevents discomfort and allows ventilation, ensuring all-day coolness.
Show More

Lee | Waylon Chukka Boot for Men | Durable & Stylish Mens Chukka Boot | Everyday Men Footwear, British Tan/Chocolate/Navy Denim, 10.5 M

Lee
M000079-2511
3.06 Pounds

Ratings for Lee (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
Amazon.com -

Features

MENS CHUKKA BOOT: Step into timeless style and everyday comfort with the Lee Waylon Chukka Boot for Men | Designed for versatility, this classic mens chukka boot silhouette pairs effortlessly with both casual and semi-formal looks, making it an ideal go-to boot for workdays, weekends, and everything in between
CHUKKA BOOTS FOR MEN: Crafted with durability in mind, the Waylon mens work boots feature quality materials built to withstand daily wear while maintaining a polished appearance | The sleek upper on this Chukka boot for men is complemented by clean stitching and minimal detailing, offering a refined yet rugged look that never goes out of style
Show More

Bruno Marc Men's Suede Leather Chelsea Ankle Boots,Size 11,1-Black,URBAN-06-1

Bruno Marc
B235-FA2BO2AG01-AA02MJ-41977615966

Ratings for Bruno Marc (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
topshoesUS 88
Amazon Resale -

Features

Soft PU Upper: These men’s Chelsea boots feature a smooth upper that is crease-resistant, making it effortless to maintain for a fresh look every time.
Lasting Comfort: Lined with a resilient PU-covered sponge insole that absorbs shock, these boots ensure every step is supported and cushioned.
Show More
Top 5

Fortis Tread Chukka Boots Mens, Comfort Arch Support for Travel and Parties

Fortis Tread
MCK001

Ratings for Fortis Tread (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
topstrideUS -

Features

ELEVATE YOUR STYLE: Features a timeless classic design with sophisticated crafted details and a sleek silhouette. This premium aesthetic delivers an immediately polished look that effortlessly catches the eye, allowing you to exude unmistakable masculine confidence during daily commutes, making these chukka boots mens an essential, high-end wardrobe staple for today's modern man
ALL-DAY COMFORT: Highlights a functional side zipper for seconds-fast entry, perfectly saving your time during hectic morning commutes. Featuring a supportive arch structure and responsive cushioned insole, these ankle boots effectively absorb shock and reduce friction, while the soft padded collar protects your ankle, ensuring you walk for hours with significantly minimized fatigue
Show More

Deer Stags Men's Rockland Dress Comfort Chelsea Boot/Redwood/Dark Brown/ 13 / Medium

Deer Stags
RCKLND-VEGA-RDDB-M-13
5.0 x 5.0 x 0.7 Inches
0.9375 pounds

Ratings for Deer Stags (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
Amazon Resale -
Amazon.com -

Features

MODERN CHELSEA BOOT LOOK: Contrast stitching and a pull tab added to these men’s dress boots for a twist on a classic
CUSHIONED MEMORY FOAM INSOLE: Soft and pillowy against your foot and exceptionally comfortable. A formal style that wears like a casual boot
Show More
Top 7

Vostey Mens Motorcycle Boots with Side Zipper Dress Boot 8200A WineRed 10.5

Vostey
BMY8200A-winered-10.5

Ratings for Vostey (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
VOSTEY -

Features

【MATERIAL】selected 100% genuine leather materials, exquisite and waterproof, retro fashion color polishing toe processing.The durable sole with non-slip pattern can provide grip and traction,suitable for any occasion.
【CONSTRUCTION】classic vintage design,these mens casual boots feature a fashionable lace-up,cap toe design.
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Top 8

HVENSTEAD Black Chukka Boots for Men: Dress Wingtip Shoes Mens Casual Work Derby Formal Chukka Boots Size 10.5

HVENSTEAD
0.3937 x 0.3937 x 0.3937 inches
0.1102 Pounds

Ratings for HVENSTEAD (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
HVENSTEAD -

Features

Mens Shoes Comfort: Mens dress shoes are made of soft materials, making you comfortable every day, they are stiff enough to provide day ankle support, them as feeling like a glove on their feet and soft provide great support, ensuring that walking is not too hard with soft leather and good cushioning, breathe well. The boots feature a lightweight design and can be paired with thick socks in winter and autumn, you will also feel comfortable and breathable in summer and spring.
Dress Shoes Style: You can choose colors according to your preferences, each color is easy to match with clothes, and can shape various styles and types, reflected fit. Mens casual shoes can also be paired with any outfit to suit your style, reflected fit, unique pattern on the sole casual chukka style combines functionality. Mens boots can be used for work, business events, formal occasions, casual activities, or attending party and travel.
Show More

ArcBrothers Mens Fashion Dress Boots - Genuine Leather Classic Brogue Style Dress Oxford Ankle Boots Gift For Men

ArcBrothers
Mens Dress Boots

Ratings for ArcBrothers (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
ArcBrothers -

Features

Oxford Style -Pleasant aesthetic classic, with a brogue upper, Classic color expression that makes people unable to can't look away; out of the box, blending retro style and high quality, Also a dress boots with a ‘little’ style with overall comfortability.
Top Craftsmanship - Goodyear welt construction for added support and durability. Combined old world style appeal and quality coupled.And the insole keep for standing for a long time ensures comfort.
Show More

FUNROMAN Men's Motorcycle Style Ankle Boots, Black Faux Leather Dress Boots with Side Zipper and Buckle Strap M01 Brown 10

FUNROMAN
2.2046 Pounds

Ratings for FUNROMAN (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
CunShang -

Features

PREMIUM MATERIAL: Crafted from high-quality faux leather with a smooth finish, these ankle boots offer a sophisticated look for daily wear and formal occasions
MOTORCYCLE-INSPIRED DESIGN: Features a stylish buckle strap detail across the ankle and a sleek black color that adds an edgy, fashionable touch to any outfit
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Jousen Chelsea Boots Casual Slip On Ankle Waterproof Mens Boots(AMY8119A brown 10)

Jousen
AMY8119A-brown-10
2.9498 pounds

Ratings for Jousen (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
JOUSEN 5,342

Features

EASY WEAR:Men shoes combined with the stretchy elastic goring,ensures a convenient on and off experience.Boots for men designed to sit above the ankle,minimize irritation.Adhering to US standard sizing guarantees a perfect fit.
SLEEK AND PRACTICAL:Whether you're at the office or enjoying your weekend,these chelsea boots men will quickly become your top choice for a stylish yet comfortable look.The contrast stitch on the midsole provides a touch of sophistication without being overly flashy.
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Top 12

Amazon Essentials Men's Cap Toe Dress Boots, Black, 11

Amazon Essentials
AEMN58733F25

Ratings for Amazon Essentials (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
Amazon.com -

Features

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Bruno Marc Men's Mid Top Chukka Sneaker Lace Up Dress Boot,Size 12,Tan,GRAND-HIGH

Bruno Marc
B205-2C5AH02-I11MK-PFEK

Ratings for Bruno Marc (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
topshoesUS 88

Features

Stay Dry Anywhere: Water-resistant PU leather upper ensures protection against splashes during daily casual wear or outdoor activities, making these men's boots reliable for versatile scenarios.
Keep Feet Cool: Breathable fabric lining prevents discomfort and allows ventilation, ensuring all-day coolness.
Show More
Top 14

Bruno Marc Men's Classic Dress Casual Chukka Boots 2.0,Size 12,Black,CHUKKA-1

Bruno Marc
B234-FA2BO2AG03-AA02MK-419563602966

Ratings for Bruno Marc (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
topshoesUS 88

Features

Soft PU Upper:These men’s Chukka boots feature a smooth upper that is crease-resistant,making it effortless to maintain for a fresh look every time.
Lasting Comfort:Lined with a resilient PU-covered sponge insole that absorbs shock,these boots ensure every step is supported and cushioned.
Show More

Clarks mens Bushacre 2 chukka boots, Beeswax, 10.5 US

Clarks
26082286
1.0 x 1.0 x 1.0 Inches
1.4375 Pounds

Ratings for Clarks (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
BHFO 1,570
Amazon.com -

Features

The finish or polish on these boots show marks which are not scratches
Chukka boot silhouette, Two eyelet lace-up front, Cushioned insole
Show More
Top 16

Bruno Marc Men's Dress Ankle Derby Boots,Brown,10.5

Bruno Marc
37683-BERGEN-01-BROWN-SZ-10.5

Ratings for Bruno Marc (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
topshoesUS 88

Features

Dress boot features a wingtip toe and brogue details with a lace-up and side zipper closure
Full-leather lining and leather-covered insole offers a set of dry feet and comfortable
Show More
Top 17

Holy dove Men's Dress Boots Side Zipper Comfort Full-Grain Leather Business Office Cap Toe Oxford Short Ankle Boot

Holy dove

Ratings for Holy dove (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
senlin xieye -

Features

【Easy Slip-On Design】: These Chukka boots for men feature a side zipper and elastic panels for quick, convenient wear. Perfect for both business and casual wear, these mens dress boots offer elegance and practicality, while the mens black Chelsea boots bring a stylish touch to any outfit.
【Non-Slip Rubber Outsole】: Durable outsole provides excellent traction on wet or slippery surfaces, making these winter dress boots for men ideal for both chilly weather and everyday wear.
Show More
Top 18

QEOSNBX Men'S Classic Leather Chunky Heel Chelsea Boots With Side Zipper Fashion Pointed Toe Elastic Band High Top Block High Heel Formal Chukka Booties For Casual Business Party Wedding (Black,12.5)

QEOSNBX
0611qex

Ratings for QEOSNBX (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
QEOSNBX -

Features

【High-Quality Leather】: The Upper Is Made Of Selected High-Quality Leather, With Fine Texture And Rich Texture, Bringing Excellent Durability And Luxurious Touch. The Inner Lining Is Made Of Soft Lining Material, Which Fits The Curve Of The Foot And Reduces Friction. It Can Remain Comfortable Even If Worn For A Long Time, Providing Intimate Care For Men'S Daily Travel.
【Fashion And Comfort】: The Unique Pointed Toe Design Highlights The Classic British Style, With Smooth And Neat Lines, Modifying The Contour Of The Foot, And Showing The Elegant Temperament Of Men. The Clever Combination Of Side Zippers And Elastic Bands Creates A Convenient Wearing And Taking Off Experience, Ensuring A Comfortable Fit, And Making Fashion And Practicality A Perfect Combination.
Show More
Top 19

Deer Stags Men's Rockland Dress Comfort Chelsea Boot/Black/ 12 / Medium

Deer Stags
RCKLND-VEGA-BKBK-M-12
5.0 x 5.0 x 0.7 inches
0.9375 pounds

Ratings for Deer Stags (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
Amazon.com -
Amazon Resale -

Features

MODERN CHELSEA BOOT LOOK: Contrast stitching and a pull tab added to these men’s dress boots for a twist on a classic
CUSHIONED MEMORY FOAM INSOLE: Soft and pillowy against your foot and exceptionally comfortable. A formal style that wears like a casual boot
Show More
Top 20

Bruno Marc Men's Dress Ankle Derby Boots,Black,10.5

Bruno Marc
37669-BERGEN-01-BLACK-SZ-10.5

Ratings for Bruno Marc (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
topshoesUS 88

Features

Dress boot features a wingtip toe and brogue details with a lace-up and side zipper closure
Full-leather lining and leather-covered insole offers a set of dry feet and comfortable
Show More

Holy dove Mens Coffee Brown Chelsea Dress Boots with Side Zipper & Slip-On Ankle Design, Genuine Leather Casual Boots for Men, Size 10

Holy dove
2.7602 pounds

Ratings for Holy dove (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
senlin xieye -
Amazon Resale -

Features

【Easy Slip-On Design】: These Chelsea boots for men feature a side zipper and elastic panels for quick, convenient wear. Perfect for both business and casual wear, these mens dress boots and side zipper boots for men offer elegance and practicality.
【Non-Slip Rubber Outsole】: Durable outsole provides excellent traction on wet or slippery surfaces.
Show More
Top 22

Arkbird Mens Dress Boots Genuine Leather Cap Toe Ankle Boot with Side Zipper for Casual Business Formal Wear

Arkbird

Ratings for Arkbird (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
Kang Best -

Features

Genuine Leather: Crafted from premium genuine leather, these mens dress boots are supple, breathable and feature a rich texture. The classic silhouette suits both business and casual occasions, highlighting a sophisticated taste.
Convenient Side Zipper: Equipped with a durable metal zipper for smooth and easy wear. This practical design offers effortless style whether you're heading to work or going out.
Show More
Top 23

Nunn Bush Men's Odell 2.0 Wingtip Dress Casual Chukka Leather Boots Black 10.5 Wide

Nunn Bush
85089-007

Ratings for Nunn Bush (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
Amazon.com -

Features

Heavyweight style combines with lightweight construction like an EVA footbed and lightweight EVA and rubber outsole to form a boot that feels as good as it looks. Casual, contemporary, and versatile, the Nunn Bush Odell 2.0 Wingtip Dress Casual Chukk
Heel pull loop.
Show More

FUNROMAN Men's Dress Boots, Wingtip Brogue Ankle Boots with Side Zipper for Business Casual M03 Black 10.5

FUNROMAN
2.2046 pounds

Ratings for FUNROMAN (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
CunShang -

Features

PREMIUM DESIGN: Classic wingtip brogue oxford ankle boots crafted with genuine leather uppers featuring decorative perforations and sophisticated stitching details
VERSATILE STYLE: Available in black and brown colors, perfect for business, formal events, weddings, and everyday professional wear
Show More
Top 25

Bruno Marc Men's Classic Chelsea Ankle Dress Boots,1-Brown,14

Bruno Marc
B235-FA2BO2AG01-AB09MM-41977615966

Ratings for Bruno Marc (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
topshoesUS 88

Features

Soft PU Upper: These men’s Chelsea boots feature a smooth upper that is crease-resistant, making it effortless to maintain for a fresh look every time.
Lasting Comfort: Lined with a resilient PU-covered sponge insole that absorbs shock, these boots ensure every step is supported and cushioned.
Show More
Top 26

Men's Captain Lace-Up Boot, Brandy, 11.5

Thursday Boot Company
BRDYCPN11-5
14.5 x 12.0 x 5.8 inches

Ratings for Thursday Boot Company (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
Thursday Boot Company -

Features

THE PERFECT FIT - We recommend ordering the size you typically wear in leather boots or dress shoes, or ½ size smaller than you typically wear in sneakers. If you have any questions, need help finding your size, or need to exchange for a different size, our team is always here to help! (Last: Encore)
THE CAPTAIN ANKLE BOOT - Complement any outfit from jeans to a business suit in this versatile minimalist boot that is handcrafted and hand stitched for a timeless look
Show More
Top 27

PARTY Mens Dress Boots - Casual Lace-up Chukka Leather Boots for Men,LINUS-BLACK-12

PARTY

Ratings for PARTY (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
MENS FOOTWEAR -

Features

Crafted from genuine leather, our boots exude luxury and sophistication, ensuring a timeless and stylish look suitable for any occasion
Our boots feature a slip-resistant sole that guarantees your safety and stability, making them the perfect choice for various terrains and weather conditions
Show More

Top 10 Men's Dress Boots - Verified to Buy (September 2026)

Top 10 Men's Dress Boots Brands on Amazon

Here is the list of top-rated brands that were evaluated by CherryPicks.

  • Bruno Marc
  • Lee
  • Fortis Tread
  • Deer Stags
  • Vostey
  • HVENSTEAD
  • ArcBrothers
  • FUNROMAN
  • Jousen
  • Amazon Essentials

Related Men's Dress Boots Guides

For more personalized Men's Dress Boots guides, Check those pages,


Top 9 Men's Dress Boots Sellers: CPR Seller Rank List

CPR sellers rank is based on CherryPicks-AI bestselling ranking system that helps us analyze each seller's sales trends. The List of top seller ranks is our in-house data, essential for our product ranking to help you make the right shopping choice.

Rank Name Yearly Feedbacks Avg. Ratings
🥇 topshoesUS 312,882 4.9
🥈 BHFO 35,459 4.5
🥉 JOUSEN 12,356 4.8
4 VOSTEY 5,456 4.8
5 Thursday Boot Company 2,127 4.6
6 Kang Best 690 4.9
7 Amazon.com 386 4.7
8 ArcBrothers 159 4.7
9 topstrideUS 12 4.8
View or download top Men's Dress Boots seller & rating report
topshoesUS [312882] BHFO [35459] JOUSEN [12356] VOSTEY [5456] Thursday Boot Company [2127] Kang Best [690] Amazon.com [386] ArcBrothers [159] topstrideUS [12] topshoesUS 85% BHFO 10% JOUSEN 3% VOSTEY 1% Thursday Boot Company 1% Kang Best 0% Amazon.com 0% ArcBrothers 0% topstrideUS 0%

[Get] Men's Dress Boots Deals (✅Exclusively for Prime)

What does "Amazon Fulfilled" Mean?

Amazon Fulfilled refers to products handled by Amazon's logistics, which indicates that the product is stored, packed, and shipped by Amazon from one of its fulfillment centers.

When you order a product that is "Amazon Fulfilled," Amazon takes care of the storage, packing, shipping, and customer service for that product. This often ensures quicker delivery and better customer service compared to products that are not fulfilled by Amazon. It also means that the product is eligible for Amazon's return policy.

What does "Prime" Mean?

"Prime" refers to Amazon Prime Member (Join Amazon Prime Now), which indicates eligibility for Prime benefits. When you see "Prime" next to a product on Amazon, This generally means that if you are  an Amazon Prime member, you can get free two-day shipping on that product, and sometimes even same-day or one-day shipping depending on your location.

Prime members also have access to other benefits, including 2-Day ShippingExclusive Member DealsPrime VideoBuy With PrimeAmazon MusicPrime Gaming, and more.

Shop Prime Men's Dress Boots Deals

What does "Free Shipping" Mean?

"Free Shipping" means that you will not be charged additional fees for the shipping of that product. However, unlike "Prime," which usually guarantees fast two-day shipping, "Free Shipping" doesn't necessarily mean fast shipping.

Sometimes there might be a minimum purchase requirement to qualify for free shipping if you are not a Prime member. For Prime members, the "Free Shipping" usually refers to the free two-day shipping that is one of the benefits of the Prime membership.


Why Should You Trust Us?

Now hundreds and thousands of Men supplies are available on Amazon, Picking the right one is not easy, and that may take a lot of your time, Right? and What is the best Men's Dress Boots to buy for new September 2026?

CherryPicks’s Methodology for Evaluating Men's Dress Boots

We developed the CherryRatings-AI system to identify and score reviews and the CherryPicks-AI ranking system that uses TensorFlow framework to generate the best list, It will help us evaluate Men items that sell on Amazon. The score of items is based on over ten parameters such as analyzing customer review content, product reviewing rating statistics, brand reputation evaluation, comparing product price with features, etc, You can visit How We Rank to learn more in detail.

We collected and analyzed 306 of Men's Dress Boots reviews based on our selection criteria. It helped us shortlist the top qualified and rated Men's Dress Boots for Men, We found that most customers choose Men's Dress Boots with an average price of $48.17, and the top brands are Amazon Essentials, Lee, Clarks, Deer Stags, Vostey, Nunn Bush, Thursday Boot Company And Arkbird

Then our expert-level editors reviewed all those quality items and selected the top 27 Men's Dress Boots for you, We have researched hundreds of sellers and picked the top sellers for Men, including Amazon Resale, topshoesUS, BHFO, JOUSEN, VOSTEY, Thursday Boot Company, Kang Best, Amazon.com, ArcBrothers And topstrideUS. The Bruno Marc Men's Dress Ankle Boots Cap Toe Lace... are available for purchase right now, and The seller of #1 rank product has received honest feedback from 1,839 consumers with an average rating of 4.4.

We've helped a lot of satisfied users get the right Clothing, Shoes & Jewelry product based on their needs, and save lots of time for them to pick Men's Dress Boots to buy.


Written By Tina Miles

Tina Miles is very opinionated when it comes to what she way — and even tends to do the same to people she meets. While her opinions can be annoying sometimes, she is on point and knows what she is doing. She would be sharing her experience to help us make the right decision on what we wear.