Five Favorite Pairs of Jeans for All Seasons

Sharing my five favorite pairs of jeans I’ve collected over the last year. Including one just purchased this week that may end up being my new favorite pair!

Five Favorite Pairs of Jeans | The Best Denim for All Seasons | Louella Reese

I’ve chatted about this before but in case you’re new here – I’ve never been much of a jeans gal. Or really a pants gal in general! Nine times out of ten I’ll reach for a dress or skirt over a pair of jeans or other style of pants. However, that has recently changed. In part to my favorite pair of pants ever and finding some really great jeans that changed the game for me. Including my mindset about jeans. So I thought it was time for me to share those fabulous styles that have made this dress/skirt gal reach for jeans a little more often! Especially since we’re slowly headed into the fall season, I say slowly because fall temps don’t seem to be showing up anytime soon. But typically fall and winter are when we all reach for jeans a little more often. So here are five pairs I would 100% recommend scooping up and adding to your fall wardrobe. Aside from why I love them, I’ve also included a little about the size and fit of each pair. 

Five Favorite Pairs of Jeans 

Five Favorite Pairs of Jeans | The Best Denim for All Seasons | Louella Reese

Everlane The Relaxed Boyfriend Jeans

Sadly, this pair has sold out (fingers ultra crossed they are restocked). However, Everlane does have another pair that is very similar, the Summer Jean. Available in a light wash, just like the pair I am wearing. As well as bone (off white) and mid-blue. Personally, the light wash in my absolute favorite (hence why I purchased my pair in the wash haha). I was convinced I need this pair of jeans after trying them on at the Everlane store in NYC. Never have a pair of jeans felt so perfectly relaxed + comfortable while still making my booty look good. Y’all that’s a tough combo to achieve, am I right? The wash was also a little different from my typical go to denim and spiced up the wardrobe a bit. 

These jeans fit well and true to size, all while not loosing their shape or stretching out after wearing. Recently, I have probably worn these jeans 10-12 times without washing and they’re just a tight/taunt every time I wear them. Which I LOVE! They are meant to be a slightly looser fit but again, still fit true to size. I feel like most times with relaxed and/or boyfriend jeans you have to go down a size but that is not the case with this pair. 

p.s. if you haven’t tried Everlane denim you need to! Such a game changer and you truly cannot beat their prices! 

Five Favorite Pairs of Jeans | The Best Denim for All Seasons | Louella Reese

Madewell 10″ High-Rise Skinny Jeans: Drop Step-Hem Edition

My most favorite pair of jeans ever! The jeans that turned me into a jean lover and encouraged me to give jeans a try again. Another pair that has unfortunately sold out (I purchased them in December) however, Madewell has several other awesome high-rise skinny jean styles. And if they’re anything like my pair (which I’m sure they are) you’ll want to absolutely live in them! Comfortable, ultra-flattering, hold you, and have just the tiniest bit of stretch to make them move with you while holding their shape FOREVER

Madewell Cali Demi-Boot Jeans in Dory Wash: Comfort Stretch Edition

My newest pair of denim aka they just arrived yesterday. That may just become my favorite pair! They’re pretty casual – perfect for everyday, day dates, and weekend life with friends. Rather than being your basic pair of everyday jeans they’re a little unique with the button front, mini-flare, and cropped leg. Great for pairing with your favorite flats, sneaks, and kitten heels. The best part about them is that they have an extra layer of hold with Madewell’s supersleek magic pockets that hold/pull you in! All while being super comfortable! 

Fit is true to size and I say would align well with those styles of Madewell denim. 

original post 

Vineyard Vines Jamie High-Rise White Denim

Can we all agree finding a great pair of white jeans is INSANELY hard? Like almost as hard as finding a swimsuit we absolutely love that fits perfectly. I’ll be honest and say it’s challenge I lost year after year after year. They were too transparent, too thick, too thin, or just plain unflattering. UNTIL I was sent this pair from Vineyard Vines. GAME CHANGED. Not transparent, not too thick, not too thin, and incredibly flattering. Extra bonus, the booty looks good in them. If you’re on the hunt for the best pair of white jeans, this pair is truly it! Perfectly high-waisted but not too high as well! 

They fit true to size and hold their shape! I would say they have a little stretch but it is very minimal and I mean that in the best way possible! 

Five Favorite Pairs of Jeans | The Best Denim for All Seasons | Louella Reese

Madewell Skinny Overalls

This style is almost sold out (only available in xx-small and x-large) however they are on SUPER sale! So if they are available in your size I would highly recommend scooping up ASAP. The exact same style in a darker wash is available in all sizes! At full price they are a little pricey but in my opinion super worth it…IF you’ll be wearing them. I think overalls are one of those styles you either feel comfortable wearing often or you don’t feel comfortable wearing but want to so you purchase but find they just sit in your closet. If you’re the latter, maybe skip on this pair or purchase the sale wash. If you’re the person that will wear them often (this gal) buy them and get to wearing! They’re seriously the most comfortable things ever and look so stinking cute! A fun way to wear jeans but spice it up a bit. 

Overall, the overalls are pretty stretchy yet they keep their shape. Meaning they’ll move right along with you but when you put them on the next time they’ll feel exactly the same as the previous time you wore them. Overalls are also great to wear all year around – paired with a tank or tee in the summer + sandals or sneaks, a flannel plus booties or cute flats for fall, and worn with a blouse + cardigan for winter with your favorite booties. I would say this style fits true to size. However, if you want them a little looser, I would go up a size or go up if you’re in between sizes. 

Shop My Favorite Pairs of Jeans 



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  1. Rachel wrote:

    The Madewell 10″ high rise skinnys are my favorite! I need to try the VV pair!


    Posted 9.11.19 Reply
    • They’re the BEST!! Freaking in love with them. And yes you really do – they’re sooo good as well. Truly the best white jeans I have ever found.

      xo Laura Leigh

      Posted 9.11.19 Reply
  2. Morgan wrote:

    Finally turned you into a jeans gal! Well, I didn’t, but I’m happy you’re part of the club now! 🙂 I wish I had more opportunities to wear those overalls and I would for sure get them! They’re SO flattering on EVERYONE!

    How 2 Wear It []

    Posted 9.12.19 Reply
    • Haha Madewell and Everlane sure did!! Couldn’t agree with you more – they are super flattering! Need to find you more opportunities to wear them 🙂

      xo Laura Leigh

      Posted 9.13.19 Reply
  3. rebecca wrote:

    LOVING your denim picks!! I feel the same way about jeans vs dresses, but sometimes they’re just right for the occasion.. The overalls are also adorable on you!

    xx rebecca // the crystal press

    Posted 9.12.19 Reply
    • Thank you so much Rebecca! Definitely agree – sometimes, they’re just what you need!

      xo Laura Leigh

      Posted 9.13.19 Reply
  4. High rise skinny jeans are my go to for the fall! Love all of these looks on you. xoxo sarah

    Posted 9.12.19 Reply
  5. I think a high rise boyfriend cut is my favorite type of jean at the moment. I also own a pair of Madewell skinny overalls that I totally adore.

    Posted 9.12.19 Reply
  6. Cathy wrote:

    Love all these denim styles on you! A girl can never have enough jeans!


    Posted 9.12.19 Reply
  7. Stephanie wrote:

    This is the first autumn that I’ve ever invested in more than one pair of one style of pants haha! I’m finally branching out to mom jeans and straight leg pants and more. It’s been fun – so I’m glad I got to read this post with all your suggestions!

    Posted 9.12.19 Reply
  8. Amanda wrote:

    Madewell always has such cool jeans styles– all these jean picks look fantastic on you!

    Posted 9.12.19 Reply
  9. Kileen wrote:

    Love the denim!! Those boyfriend jeans are so cute, and swooning over those overalls!

    cute & little

    Posted 9.13.19 Reply
  10. Laura S wrote:

    These are all so cute! Loving the overalls!

    Posted 9.13.19 Reply
  11. Caitlin wrote:

    I totally need a new pair of jeans for the fall and have to go on a shopping trip to try on all these – esp the high rise from Madewell! And maybe some overalls 🙂

    Posted 9.16.19 Reply
  12. Kristina wrote:

    I fell in love with Madewell jeans this year, they really are the best!

    Posted 9.17.19 Reply