Best Men's Timberland Slip-On Boots (Aug. 2026) - Rated by CherryPicks' Experts

At a Glance: Our Top Picks

Top 1

Timberland mens Mt. Maddsen Slip on Hiking Shoe, Dark Brown, 9 US

9.9
CPR Score
Top 2

Timberland PRO Men's Nashoba Soft Toe Industrial Casual Work Boot, Stout Brow...

9.7
CPR Score
Top 3

Timberland PRO Men's Pro Wedge 6 Inch Moc Soft Toe Industrial Work Boot, Brow...

9.7
CPR Score
Tips

Based on our evaluations of 97 Men's Timberland Slip-On Boots and the analysis of over 122,824 consumer satisfaction reviews, We made this top list for Men's Timberland Slip-On Boots for Sport Specific Clothing.

* 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 Timberland Slip-On Boots Rated by CherryPicks

Market Overview
Men's Timberland Slip-On Boots Reviewed
  • Reviews Analyzed: 122,824 Items
  • CPR Avg. Rating: 8.7 / 10
26 Products Evaluated
  • Highest Price: $220.00
  • Lowest Price: $44.00
  • Avg. Price: $142.90
Price Disclaimer

Top 26 Men's Timberland Slip-On Boots on Amazon (Verified You can Buy)

Top 1

Timberland mens Mt. Maddsen Slip on Hiking Shoe, Dark Brown, 9 US

Timberland
TB0A1QLSD71
2.0 pounds

Ratings for Timberland (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
Amazon.com -
Orva Stores 85

Features

There's lots to love about our Mt. Maddsen leather shoes. They slip on, so you won't waste any time on laces. They feature rugged, clean good looks, grippy outsoles and amazing comfort.
LOOK NO FURTHER for trail-ready performance and style. Our selection of men’s hiking boots, waterproof hiking boots, casual boots, and casual shoes is designed to fit in with your outdoor-ready ensembles.
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Top 2

Timberland PRO Men's Nashoba Soft Toe Industrial Casual Work Boot, Stout Brown-2024 NEW, 10.5M

Timberland PRO
TB1A2NY3214
15.35 x 10.55 x 5.59 inches

Ratings for Timberland PRO (CPR Score)

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

Features

Anti-Fatigue Technology: A comfort system designed with shock-absorbing, geometrical technology that returns energy back to the foot to deliver all-day support and comfort.
Electrical Hazard Protection: Provides secondary underfoot protection against live electrical circuits, electrically energized conductors, parts or apparatus and meets ASTM F2412-18a, ASTM F2413-18, ASTM F2892-18 standards.
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Top 3

Timberland PRO Men's Pro Wedge 6 Inch Moc Soft Toe Industrial Work Boot, Brown-2024 New, 9.5

Timberland PRO
TB153009214
2.1 pounds

Ratings for Timberland PRO (CPR Score)

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

Features

Timberland PRO 24/7 Comfort System: A unique comfort system that meets the most rigorous worksite demands- 24 hours a day, 7 days a week- the Timberland PRO 24/7 comfort suspension system technology helped reduce foot fatigue, supports the arch and cushions every step
Electrical Hazard Protection: Provides secondary underfoot protection against live electrical circuits, electrically energized conductors, parts or apparatus and meets ASTM F2412-18a, ASTM F2413-18, ASTM F2892-18 standards.
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Top 4

Timberland PRO Men's Morphix BOA 6 Inch Composite Safety Toe Waterproof Industrial Work Boot, Blackout Leather, 11.5 M US

Timberland PRO
TB0A438GENR
0.9 Pounds

Ratings for Timberland PRO (CPR Score)

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

Features

BOA Fit System: delivers micro-adjustable, precision fit engineered to perform in the toughest conditions.
Anti-Fatigue Technology: A comfort system designed with shock-absorbing, geometrical technology that returns energy back to the foot to deliver all-day support and comfort.
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Top 5

Timberland Men's Britton Road Mid Chelsea Boot, Rust Full Grain, 12 Medium

Timberland
TB0A6A4W
2.4 Pounds

Ratings for Timberland (CPR Score)

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

Features

Premium Timberland Leather: By purchasing this product, you are supporting Leather Working Group certified tanneries.
Anti-Fatigue Technology: A comfort system, adopted from Timberland PRO, designed with shock-absorbing, geometrical technology that returns energy back to the foot to deliver all-day support and comfort.
Show More
Top 6

Timberland PRO Men's Nashoba Composite Safety Toe Industrial Casual Work Boot, Black-2024 NEW, 15M

Timberland PRO
TB1A2P3R001
4.751 Pounds

Ratings for Timberland PRO (CPR Score)

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

Features

Anti-Fatigue Technology: A comfort system designed with shock-absorbing, geometrical technology that returns energy back to the foot to deliver all-day support and comfort.
CarbonShield Technology: Engineered with nanotechnology, adds strength and unmatched protection, provides a better fit and reduces weight with a lightweight, non-metallic, asymmetrical-shaped toe cap that meets US safety standards including ASTM F2412-18a and ASTM F2413-18 I and C impact and compression safety standards.
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Top 7

Timberland PRO Men's Irvine Chelsea Wedge Soft Toe Industrial Work Boot, Medium Brown, 10.5M

Timberland PRO
TB0A66BUEM4
3.4833 Pounds

Ratings for Timberland PRO (CPR Score)

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

Features

Anti-Fatigue Technology: A comfort system designed with shock-absorbing, geometrical technology that returns energy back to the foot to deliver all-day support and comfort.
Timberland PRO Rubber: Heat-resistant, durable rubber compound offers enhanced slip, oil and abrasion resistance.
Show More

Carhartt Men's Wedge 5" Chelsea Pull-On Soft Toe FW5033-M Boot, Dark Bison Oil Tanned, 11

Carhartt
FW5033-M
13.89 x 12.71 x 5.2 inches
3.1 pounds

Ratings for Carhartt (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
DUNGAREES 2,643
Amazon.com -

Features

Soft Toe. Identifies Non-Safety soft toe intended for use in environments where protective safety toes are not needed or required.
Insite Technology Footbed. Carhartt footbed made with Insite technology is engineered to create maximum arch support to reduce foot fatigue during long days on the job.
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Top 9

Timberland PRO Men's Boondock Ultralight Pull-On Composite Safety Toe Waterproof Industrial Work Boot, Medium Brown, 13 Wide

Timberland PRO
TB0A6473EM4
15.1 x 14.9 x 5.5 inches
4.21 pounds

Ratings for Timberland PRO (CPR Score)

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

Features

Ventilated Anti-Fatigue Technology: A comfort system designed to promote air-flow for better climate control and increased comfort while offering industry-leading shock-absorption and energy return via geometrical technology that delivers all-day support and cushioning.
HoverSpring: Our proprietary lightweight HoverSpring foam provides industry leading underfoot comfort and flexibility while being durable enough for the harshest environments.
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Top 10

Lugz Men's Fringe Fashion Boot, Black Durabrush, 9.5 D US

Lugz
MFRGD-001
14.9 x 12.4 x 5.0 inches
1.35 Pounds

Ratings for Lugz (CPR Score)

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

Features

Moc toe design
Padded tongue and collar
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Top 11

Timberland PRO Men's True Grit Chelsea Composite Safety Toe Waterproof Industrial Western Work Boot, Dark Brown, 12 Wide

Timberland PRO
TB0A67QKW01
4.21 pounds

Ratings for Timberland PRO (CPR Score)

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

Features

Anti-Fatigue Technology: A comfort system designed with shock-absorbing, geometrical technology that returns energy back to the foot to deliver all-day support and comfort.
CarbonShield Technology: Engineered with nanotechnology, adds strength and unmatched protection, provides a better fit and reduces weight with a lightweight, non-metallic, asymmetrical-shaped toe cap that meets US safety standards including ASTM F2412-18a and ASTM F2413-18 I and C impact and compression safety standards.
Show More
Top 12

Timberland PRO Men's Direct Attach 8 Inch Soft Toe Insulated Waterproof Industrial Work Boot, Marigold-2024 New, 9

Timberland PRO
TB1A29X8214
14.25 x 12.17 x 5.59 inches
3.4 Pounds

Ratings for Timberland PRO (CPR Score)

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

Features

Anti-Fatigue Technology: A comfort system designed with shock-absorbing, geometrical technology that returns energy back to the foot to deliver all-day support and comfort.
Waterproof Seam-Sealed: Seam-sealed waterproof leather for durable waterproof protection with special tanning that repels moisture for waterproof protection.
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Top 13

Timberland PRO Men's True Grit Pull On Composite Safety Toe Waterproof Industrial Western Work Boot, Brown Turkish Rancher-2024 NEW, 10.5 M US

Timberland PRO
TB1A2297214
15.31 x 15.0 x 5.59 inches
4.21 pounds

Ratings for Timberland PRO (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
SR Max 7,473

Features

Anti-Fatigue Technology: A comfort system designed with shock-absorbing, geometrical technology that returns energy back to the foot to deliver all-day support and comfort.
CarbonShield Technology: Engineered with nanotechnology, adds strength and unmatched protection, provides a better fit and reduces weight with a lightweight, non-metallic, asymmetrical-shaped toe cap that meets US and Canadian safety standards including ASTM F2412-18a and ASTM F2413-18 I and C impact and compression safety standards and CAN/CSA-Z195-14 Grade 1.
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Top 14

Timberland Men's Redwood Edge Essential Chelsea Boot, Brown, 13 Medium

Timberland
TB0A6CVEEM4

Ratings for Timberland (CPR Score)

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

Features

Premium Timberland Leather: By purchasing this product, you are supporting Leather Working Group certified tanneries.
Anti-Fatigue Technology: A comfort system, adopted from Timberland PRO, designed with shock-absorbing, geometrical technology that returns energy back to the foot to deliver all-day support and comfort.
Show More
Top 15

Timberland Men's Britton Road Mid Chelsea Boot, Black Full Grain, 11.5 Medium

Timberland
TB0A6A4W
2.4 Pounds

Ratings for Timberland (CPR Score)

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

Features

Premium Timberland Leather: By purchasing this product, you are supporting Leather Working Group certified tanneries.
Anti-Fatigue Technology: A comfort system, adopted from Timberland PRO, designed with shock-absorbing, geometrical technology that returns energy back to the foot to deliver all-day support and comfort.
Show More
Top 16

Timberland PRO Men's True Grit Pull On Soft Toe Waterproof Industrial Western Work Boot, Medium Brown, 8.5 Wide

Timberland PRO
TB0A42JGEM4
4.21 pounds

Ratings for Timberland PRO (CPR Score)

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

Features

Anti-Fatigue Technology: A comfort system designed with shock-absorbing, geometrical technology that returns energy back to the foot to deliver all-day support and comfort.
Waterproof Membrane: Delivers maximum waterproof protection and meets ASTM F1671-07 safety standard.
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Top 17

Irish Setter Marshall 11" Mens Steel Toe Work Boot, Brown/Olive, 11 W

Irish Setter
83930
9.06 Pounds

Ratings for Irish Setter (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
Bay 15 161
Amazon Resale -

Features

Meets ASTM Safety Standards: This leather non-metallic safety toe work boot with HRO designed rubber outsole is slip, heat, impact, compression, and electrical hazard resistant to meet ASTM F2413-18, M/I/C, EH and ASTM F3445-21, SR safety standards. HRO soles are heat resistant to melting at a minimum of 475º Fahrenheit.
Steel Safety Toe: Steel safety toe provides an additional protective layer of defense from many hazards that may be encountered at a worksite.
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Top 18

Timberland Men's Premium 6 Inch Lace Up Waterproof Boot, Wheat-NEW 2024, 12 Medium

Timberland
TB110061713
14.0 x 9.0 x 5.0 inches
3.0 pounds

Ratings for Timberland (CPR Score)

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

Features

TIMELESS ICON, the Original Yellow Boot has been breaking cultural and societal barriers for over 50 years
ALL-SEASON-STYLE gives you tireless waterproof performance and instantly recognizable work-boot style
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Top 19

Timberland Men's Originals Earthkeepers 6 inch Boot, Medium Brown, 11 Medium

Timberland
TB015551210
14.0 x 11.5 x 6.0 inches
1.41 Pounds

Ratings for Timberland (CPR Score)

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

Features

We recommend buying boots a size down from your usual sneaker size, so if you’re a sneaker size 11 order a size 10.5
Premium full-grain leather uppers
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Top 20

Timberland PRO Men's True Grit Pull On Composite Safety Toe Waterproof Industrial Western Work Boot, Medium Brown, 9.5 Medium

Timberland PRO
TB0A64CQEM4
4.21 pounds

Ratings for Timberland PRO (CPR Score)

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

Features

Anti-Fatigue Technology: A comfort system designed with shock-absorbing, geometrical technology that returns energy back to the foot to deliver all-day support and comfort.
CarbonShield Technology: Engineered with nanotechnology, adds strength and unmatched protection, provides a better fit and reduces weight with a lightweight, non-metallic, asymmetrical-shaped toe cap that meets US safety standards including ASTM F2412-18a and ASTM F2413-18 I and C impact and compression safety standards.
Show More
Top 21

Timberland Men's Flume Mid Waterproof Hiking Boot, Dark Brown-NEW 2024, 10.5 Wide

Timberland
TB118128242

Ratings for Timberland (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
Orva Stores 85

Features

Upper made with waterproof Premium Timberland Leather
Fully gusseted tongue
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Top 22

Timberland Men's White Ledge Mid Waterproof Hiking Boot, Brown-NEW 2024, 10 Wide

Timberland
TB112135214

Ratings for Timberland (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
Orva Stores 85

Features

Upper made with waterproof Premium Timberland Leather
Fully gusseted tongue
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Top 23

Timberland PRO Men's Pac Max 10 Inch Lightweight Boot Liner, Blue/Black, 11W

Timberland PRO
TB0A5TTB484

Ratings for Timberland PRO (CPR Score)

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

Features

Anti-Fatigue Technology: A comfort system designed with shock-absorbing, geometrical technology that returns energy back to the foot to deliver all-day support and comfort.
ReBOTL Material: Products with ReBOTL material contain at least 50% recycled PET (recycled polyethylene terephthalate, the stuff plastic bottles are made of) excepting trace materials.
Top 24

Timberland Men's Mt. Maddsen Anti-Fatigue Hiking Wateproof Leather Hiking Boot, Dark Brown Full-Grain, 12 Wide

Timberland
TB12730R242
3.2 pounds

Ratings for Timberland (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
Orva Stores 85

Features

Upper made with waterproof Premium Timberland Leather
Fully gusseted tongue
Show More
Top 25

Timberland PRO Men's Powertrain Sport Alloy Safety Toe Static Dissipative Industrial Athletic Work Shoe, Black/Grey, 11.5 M

Timberland PRO
TB0A1B6U001
14.0 x 9.3 x 5.1 inches
1.31 Pounds

Ratings for Timberland PRO (CPR Score)

Seller CPR Rank Amazon Fulfilled Prime Free Shipping
SR Max 7,473

Features

KEEP IT COMFORTABLE: Athletic styling gives these men’s Powertrain Sport work shoes a modern look; Alloy safety toes, breathable mesh linings, static dissipative protection & anti-fatigue technology combine for ultimate low-profile comfort & protection
SAFETY AND COMFORT: Built on a tradition of craftsmanship & innovation, Timberland PRO helps you conquer your work day; Technology like our proprietary outsole with built-in Anti-Fatigue Technology keeps you comfortable all day
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Top 26

Timberland Men's Redwood Falls Chelsea Boots, Saddle, 13 Medium

Timberland
TB0A288FF13
3.0 pounds

Ratings for Timberland (CPR Score)

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

Features

Premium Timberland Leather: By purchasing this product, you are supporting Leather Working Group certified tanneries.
Anti-Fatigue Technology: A comfort system, adopted from Timberland PRO, designed with shock-absorbing, geometrical technology that returns energy back to the foot to deliver all-day support and comfort.
Show More

Top 10 Men's Timberland Slip-On Boots - Verified to Buy (August 2026)

Top 5 Men's Timberland Slip-On Boots Brands on Amazon

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

  • Timberland
  • Timberland PRO
  • Carhartt
  • Lugz
  • Irish Setter

Related Men's Timberland Slip-On Boots Guides

For more personalized Men's Timberland Slip-On Boots guides, Check those pages,


Top 5 Men's Timberland Slip-On 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.

  • 1. Orva Stores : 317,621 Yearly Feedback , Avg. Ratings 4.9
  • 2. Bay 15 : 207,712 Yearly Feedback , Avg. Ratings 4.9
  • 3. DUNGAREES : 22,910 Yearly Feedback , Avg. Ratings 4.6
  • 4. SR Max : 9,075 Yearly Feedback , Avg. Ratings 4.8
  • 5. Amazon.com : 386 Yearly Feedback , Avg. Ratings 4.7
Rank Name Yearly Feedbacks Avg. Ratings
🥇 Orva Stores 317,621 4.9
🥈 Bay 15 207,712 4.9
🥉 DUNGAREES 22,910 4.6
4 SR Max 9,075 4.8
5 Amazon.com 386 4.7
View or download top Men's Timberland Slip-On Boots seller & rating report
Orva Stores [317621] Bay 15 [207712] DUNGAREES [22910] SR Max [9075] Amazon.com [386] Orva Stores 57% Bay 15 37% DUNGAREES 4% SR Max 2% Amazon.com 0%

[Get] Men's Timberland Slip-On 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 Timberland Slip-On 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 Sport Specific Clothing 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 Timberland Slip-On Boots to buy for new August 2026?

CherryPicks’s Methodology for Evaluating Men's Timberland Slip-On 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 Sport Specific Clothing 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 97 of Men's Timberland Slip-On Boots reviews based on our selection criteria. It helped us shortlist the top qualified and rated Men's Timberland Slip-On Boots for Sport Specific Clothing, We found that most customers choose Men's Timberland Slip-On Boots with an average price of $142.90, and the top brands are Carhartt, Timberland, Lugz, Timberland PRO And Irish Setter

Then our expert-level editors reviewed all those quality items and selected the top 26 Men's Timberland Slip-On Boots for you, We have researched hundreds of sellers and picked the top sellers for Sport Specific Clothing, including Amazon Resale, Orva Stores, Bay 15, DUNGAREES, SR Max And Amazon.com. The Timberland mens Mt. Maddsen Slip on Hiking Shoe... are available for purchase right now, and The seller of #1 rank product has received honest feedback from 1,309 consumers with an average rating of 4.6.

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 Timberland Slip-On 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.