I'm a boomer (32), is it weird to rock Timberlands in this baggy style?

I’m a boomer (32), is it weird to rock Timberlands in this baggy style? Just got some really cool baggy jeans and some timberlands and the fit is on point. I don’t want to come off as a try hard though (I do’t really think I am, but it is a more Zoomer motif lately, so feels slightly weird since I’m autistic and overthink shit like this despite the fit being fire).

22 thoughts on “I'm a boomer (32), is it weird to rock Timberlands in this baggy style?

  1. Anonymous says:

    Your generation literally started the baggy style and you are asking little anime gays on this website if it’s ok to wear it?

    • Anonymous says:

      well my personal generation was skinny jeans during the emo/"indie sleeze" eras (god i hecking hate that phrase "indie sleeze" kek), but yeah on the rnb/rap sides, shit was baggy for sure. good point anon.

    • Anonymous says:

      >miltard
      >started the baggy style

      gen X Madchester/Skaters started it, miltards did the exact opposite with their hipster skinny jeans shit

      • Anonymous says:

        >Your generation literally started the baggy style
        nah that was a few years before him
        people around 30 now started the skinny indygay style

        They did both. 32 year olds first wore jnco sugger baggy jeans as kids then into highschool we all wore relatively baggy jeans and pacsun brands like famous stars and straps and dc/ or American eagle and Abercrombie in the other direction. If your basketball shorts didn’t go over your knees you were gay.

        There was also the "scene" kids as another offshoot that did wear the skin tight jeans.

        After around 2010 the more slim jean wave came along.

    • Anonymous says:

      >Your generation literally started the baggy style
      nah that was a few years before him
      people around 30 now started the skinny indygay style

      • Anonymous says:

        Boomers II (a/k/a Generation Jones)* 1955 – 1964 60 – 69
        Boomers I* 1946 – 1954 70 – 78

        Millennials 1981 – 1996 28 – 43

        As you can see, different generations.

          • Anonymous says:

            If you believe anything is what you wish it to be, then knowledge itself is worthless, and learning itself is worthless, and not only this, but you are also deceiving yourself and letting yourself live in a state of willed ignorance, which is shameful.

            You don’t want live in ignorance, because what will seem good to you at one time will actually be bad for you, and no human being really wants what is bad for them.

      • Anonymous says:

        yup, stupids on /fashion/ have not only fallen out of touch with fashion but have falllen out of touch with memes.

  2. Anonymous says:

    this tiktok instsgram explore page baggy prep nyc ripped bullshit gotta heck off already. i cant be the only one sick of this cosplay gay shit of tryhards trying to pull this look for their next "fit" if youre going to wear this shit wear it without care / putting it in spotlight like a normal man / woman trust me nobody gives a heck that youre wearing this look

  3. Anonymous says:

    its fine. timbs and baggy pants is the classic nyc nigga look people over 50 still wear so its not even out of place.
    but doing this while being a whitoid means youll attract more judgement from other white demons that think youre too old to be dressing in anything but worn out landscaping outfits and skin tight muffintop restricting banana republic polos to signal youre a marriage hostage wagecuck like them.

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