Originally meant for construction jobs and manual labor, Timberland boots have transformed into a versatile and iconic fashion statement over the past few decades. From flannels and jackets to dresses and peacoats, these sturdy boots work well with a variety of different ensembles. If you’re in need of a little inspiration, take a peek at this list to help you get started.

Expert Q&A

  • Question
    What kind of pants go best with timberlands if I'm a girl?
    Kalee Hewlett
    Kalee Hewlett
    Image Consultant
    Kalee Hewlett is a Celebrity Stylist & Confidence Coach with almost two decades of experience helping clients build confidence and ‘dress for success.' She works with her clients to transform their sense of self 'from the inside out’ by merging her expertise in image consulting with Neuro-Linguistic Programming. Kalee’s work is rooted in science, style, and the understanding that ‘identity is destiny'. She uses her own methodology and Style To Success Strategy to create positive identity shifts. Kalee is a fashion TV host and appears regularly on QVC UK sharing her fashion expertise. She also was appointed as the head judge and host of Fashion One Network’s 6-part TV show 'Design Genius.’
    Kalee Hewlett
    Image Consultant
    Expert Answer
    Timberland boots look great with boyfriend jeans if you want to go for a more laid back look. They're also great with skinny jeans or leggings and some thick cable-knit socks.
  • Question
    What top works best with timberlands and jeans if I'm a girl?
    Kalee Hewlett
    Kalee Hewlett
    Image Consultant
    Kalee Hewlett is a Celebrity Stylist & Confidence Coach with almost two decades of experience helping clients build confidence and ‘dress for success.' She works with her clients to transform their sense of self 'from the inside out’ by merging her expertise in image consulting with Neuro-Linguistic Programming. Kalee’s work is rooted in science, style, and the understanding that ‘identity is destiny'. She uses her own methodology and Style To Success Strategy to create positive identity shifts. Kalee is a fashion TV host and appears regularly on QVC UK sharing her fashion expertise. She also was appointed as the head judge and host of Fashion One Network’s 6-part TV show 'Design Genius.’
    Kalee Hewlett
    Image Consultant
    Expert Answer
    A classic denim shirt or a lumberjack flannel are great options. You can also go for the classic white T.
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About This Article

Kalee Hewlett
Co-authored by:
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This article was co-authored by Kalee Hewlett and by wikiHow staff writer, Janice Tieperman. Kalee Hewlett is a Celebrity Stylist & Confidence Coach with almost two decades of experience helping clients build confidence and ‘dress for success.' She works with her clients to transform their sense of self 'from the inside out’ by merging her expertise in image consulting with Neuro-Linguistic Programming. Kalee’s work is rooted in science, style, and the understanding that ‘identity is destiny'. She uses her own methodology and Style To Success Strategy to create positive identity shifts. Kalee is a fashion TV host and appears regularly on QVC UK sharing her fashion expertise. She also was appointed as the head judge and host of Fashion One Network’s 6-part TV show 'Design Genius.’ This article has been viewed 74,164 times.
8 votes - 87%
Co-authors: 6
Updated: February 19, 2023
Views: 74,164
Categories: Boots
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