How to Update Your Leggings Outfit Part II

October 31, 2025

I’ve been doing a really fun series over on Instagram about how to update your outfits from 2019. I feel like most of my blog and Instagram followers are my age – millennials just trying to keep up with ever changing trends. It seems to have really struck a cord. We grew up on leggings as pants and skinny jeans. Now in the age of wide leg, looser everything: what do we wear?! Today is for you! This is how to update your leggings outfit part II. You can find part one here which centers more on keeping the actual leggings base and updating it.

Leggings Outfits in 2019

Back in 2019, leggings as pants ruled the day with longer, tunic style sweatshirts and lower profile sneakers. Ankle socks were all the knew and we always showed our ankles. I wore and loved this look in all variations!! No shame if you are still rocking this look. This is meant to be helpful, not shameful. If you like it, wear it.

How to update your leggings outfit from 2019 to a. modern 2025 version with a few easy swaps!!

2025 Update

Here’s an easy way to update our favorite grey sweatshirt and leggings outfit for 2025.

  • Swap your leggings for a wider leg pant. These from Amazon are literally the best!! One of my all time best selling Amazon items. Soooo comfy. Honestly way more comfortable than leggings. They come in multiple colors and inseam lengths.
  • Trade your longer sweatshirt for a shorter version like this one.
  • Consider adding a white t-shirt underneath. It’s amazing what that small detail will do to elevate your outfit!
  • Update your sneakers for a trendy version like mine.
  • Add modern accessories like my favorite 3-in-1 Amazon bag and sunglasses.
How to update your leggings outfit from 2019 to a. modern 2025 version with a few easy swaps!!

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4 Comments

  • Reply Sprunki January 22, 2026 at 2:20 am

    I love how you’re embracing the evolving fashion trends! Your insights on updating leggings outfits are so relatable for millennials. For a fun twist, check out this game that combines music and unique characters: Sprunkiスプランキー. Can’t wait for more tips!

  • Reply solitaireonline December 11, 2025 at 9:15 pm

    Love this Part II! Your updated leggings outfit ideas are so practical and stylish. It’s amazing how a few small changes can make leggings feel fresh and put-together. Thanks for the inspo — definitely trying some of these combos!
    https://solitaireonline.ro/

  • Reply wordlefi December 10, 2025 at 1:39 am

    The guide on how to update your leggings outfit part II looks so helpful I love the styling tips and creative ideas Perfect for making everyday outfits more stylish Thanks for sharing these tips I cant wait to try them out
    https://wordle.fi/

  • Reply mahjongspiele December 9, 2025 at 8:46 pm

    Loved these fresh ideas The outfit updates you shared make leggings feel so much more polished and fun and the tips are super easy to try in everyday looks
    https://mahjongspiele.com/

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