How to Style Fashion Hiker Boots

Fashion hiker boots are a huge trend for winter 2019, and I’m here for it.

I love the casual-chic vibe with a rugged edge, and best of all, they’re as functional as they are practical. Of course I had to try a pair!

I went right to the Nordstrom shoe department, and I found so many great options, I couldn’t choose just one. I ended up coming home with two pairs to style for you. Let’s call it research, m’kay?

The first pair is by Caslon, and I’m seriously impressed with these boots. They’re incredibly comfortable inside, and they look great on. They’re also water-resistant, so you can wear them in the rain and snow.

How to Wear Fashion Hiker Boots

A lot of fashion hiker boots have a high heel, but I wasn’t sure I could pull that off. I didn’t necessarily want them to be flat either, and these have the perfect 2 1/4″ heel (plus there’s a platform so the heel drop isn’t that high.)

They’re leather on the outside, and while it says synthetic inside, they feel soft and leather-like. They also have good arch support, for those who need that.

The styling is rugged yet refined, and I love the attention to detail — like the contrast leather piping along the footbed.

These boots are true to size, or size up if in between. I went up to an 8.5 for these, in case I want extra room for socks. (For reference, I’m generally between and 8 and 8.5 in boots.)

There are so many ways to style fashion hiking boots, but I kept this look simple with a cozy sweatshirt and jeans.

This sweatshirt is soooooo soft and cozy. It’s almost fleecy in texture, but it’s on the thinner side, and I really like the styling.

The boatneck and raglan sleeves are universally flattering, and it has a slouchy but not sloppy fit. I sized up to a medium for some extra wiggle room and in case it shrinks some.

Fashion hiker boots are a huge trend for winter 2019, and I'm here for it. I'm sharing the two pairs I added to my wardrobe and how to style them.

Outfit Details:

Caslon boots // sweatshirt // jeans // similar earrings

I also fell in love with the UGG Quincy boots.

While the Caslon boots (above) were more of what I had in mind when I went shopping for fashion hiker boots, these UGGs were calling my name from the moment I laid eyes on them, and I couldn’t resist giving them a try.

These boots are lined completely with shearling and UGGpure (a textile made entirely from wool but shaped to feel and wear like genuine shearling) and they feel absolutely magical on my feet.

They’re also incredibly lightweight and have a low 1″ heel for supreme comfort. FYI, I needed a 9 in these, so I recommend sizing up at least half from your normal.

A fun thing about these boots is you can wear them with the shaft standing up, or fold it over and make them shorter.

How to Wear Fashion Hiking Boots this Winter

First, I styled them with the back folded over. There’s even a snap on the back, if you want to make sure it stays in place.

And here’s how they look if you leave the shaft standing tall.

fashion hiking boots outfit

Either way, I wore my skinny jeans tucked into these boots for a long, lean leg line and an uncluttered look.

When you cuff your jeans, you break up the line of the leg and create another point of interest, but I wanted to keep it simple with these casual boots. It’s also warmer this way!

I styled these boots with the same jeans as above, along with a dolman sweater and a plaid scarf.

This scarf is so pretty, and it comes in two other color combos if you’re not into the rust tones. I feel like this scarf should work for people with cool or warm undertones, because it has both cool and warm colors in it.

Don’t forget that Christmas is coming! A scarf makes a great holiday gift, and at $35, this one won’t break the budget.

Fall Scarf Outfit

I love this cozy look for all sorts of events and venues. You could throw on a coat on for extra warmth, or go without if you’re going to be in and out of stores and don’t want the extra bulk.

What are your thoughts on the fashion hiking boot trend? Are you in, or are you out?

Fashion hiker boots are a huge trend for winter 2019, and I'm here for it. I'm sharing the two pairs I added to my wardrobe and how to style them.

Outfit Details:

UGG boots // sweater // scarf // jeans // similar earrings // sunnies

Shop More Fashion Hiker Boots at Nordstrom:

If you’re looking for more outfit inspiration this season, check out my brand new Nordstrom Looks page where I’ve curated outfits to help you get through the holidays!

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photos: Alison Cornell

Join The Conversation

34 Responses

  1. I like this trend! Very cute! I noticed they had several styles at DSW when I was in there yesterday! Might have to give them a try. I really like the Caslon pair!

  2. I had noticed the Caslon on your Saturday try-on post I think. Very cute but I REALLY like the UGGs. I have a pair of combat-style UGG boots that I wear ALL the time, and they are so warm. That second outfit is my favorite. 🙂

  3. How cool is that, your own page!  I checked it out, very nice!  Great outfits!  Love those boots.  Actually the whole outfit looks so comfy and stylish.  That scarf is perfect.  You truly have been blessed with the knack for putting an outfit together. Have a great day!  

  4. These are a great option when I need to run around in the “muck” that happens in Minnesota. I get a lot of use out of hiker type boots in winter. Well until it gets too deep and full on Sorel snow boots need to come out that is. 😏 

  5. I like the Uggs the best. They look so cute with the cuff down. My experience with Uggs is that they always run small, but they are really good shoes. Another commenter mentioned combat style boots. I also have some of those I absolutely love, and I feel like they have a similar vibe. Hope they’re not going to go completely out.

  6. Both of these outfits suit my extra-casual lifestyle! What size Caslon dolman top are you wearing? I usually wear a small, but I’m small chested. Dolman’s sometimes overwhelm me.

  7. Congrats on your own Nordstrom page. Well deserved and oh so COOL!  Love the Caslon boots. Perfect for the chilly weather, just before (or this year – inbetween) the days with snow accumulation.  A practical trend. Yay!

  8. I’m getting used to the boots-I finally gave in and got a pair of Ugg combat looking boots! I have 3 sons and a nephew 15,19,21,25-I had already ordered 3 of the things on the list, now want 1 more each! Great list!
    But THE BEST is your page on Nordstrom!!! You hit the jackpot-how cool is that?????

  9. This post has perfect timing.. I’ve been searching for a boot this style but in doing so trying to stay away from what can feel like a heavy boot. I like both pairs but I’m a huge UGG fan( I wear mine with bare feet). This has sent me back to the drawing board for sure.
    Thanks for showing these. Thumbs up 👍 on this trend.

  10. I’m in – with my youngest still playing high school football here in Canada, I need these for game nights and also walking the dogs. They have really come a long way and finally made functional boots fashionable. Yay!

  11. Congratulations on your Nordstrom page. It is just great and so helpfull. What a wonderful accomplishment. I love those Uggs!

  12. I’m in with this trend. I have a pair of Timberlands and wear them a lot. It’s a real casual vibe and great for walks on rough ground or when it’s wet. I wear mine all winter as we rarely get snow. They just need a little waterproofing a couple of times a year. 
     I love the Marc Fisher boots but hate that it is real shearling. I might try the UGGS to get that look. 

  13. I am not sure about this trend. I feel like it is a little too masculine for my taste, but I guess it will work for some.

  14. That is oh so cool that you have your own page on Nordstrom, now!  It looks great!  Also, I am thrilled to see your post on the hiking boots.  I have been struggling with boots/shoes this year and I did come across a pair of hiking boots that I’ve had for several years, the other day.  Now, I feel like I should try those!  They might be just what I need.  Thanks!

  15. I love the second look with the UGG Hiker Books. Really not a bad price. I also love the Gray Caslon boots. A really good look. You look great in both outfits. Love your blog. Keep it coming! Great Ideas!! …..Linda W.

  16. I love both of these boots and you style them so well. I wouldn’t hesitate to buy them if I lived in the North like you do. Living in south Texas, I barely have enough time to get any wear out of my booties which I love the way they look so take every opportunity to wear them . But then 75-80 degrees comes right back sooo, well you get my point. Also the teen boys gift ideas are great – I find it very difficult to buy for boys and young men.

  17. I’m definitely IN when it comes to these boots! I’ve recently purchased two pair, but wasn’t really sure if I should tuck my jeans or cuff them. Your post is very timely and helpful! I love how you styled both pairs. 

  18. I love my warm boots.  I’ve got one pair that I wear out hunting to keep my feet warm, but I can and should wear them with my jeans.  It’s great to know that the Calson boots have arch support.  I hope you had a great day!

  19. Love both pairs of boots. So good in the cold, snowy weather and they look great too! Congrats on your Nordstrom page Jo-Lynne! You do such a nice job styling all the outfits.

  20. I have been noticing hiking boots but hadn’t really put it together in my mind, so thanks! And I love them! So cute and cozy looking! A fun look!

  21. My husband, who is a hiker, talked me into trying hiking, and just 2 weeks ago I bought a pair of (cute but functional) hiking boots. On the day of the hike, I said, “Wait a minute! I don’t know how to style these!” So your timing on this is PERFECT! LOL Also, it’s nice to know they are trending. I will now wear the boots for things other than going through the woods! I loved the look with the scarf.

  22. I have JCrews on my Christmas list-but they only come in whole sizes, have you tried these on? 
    As a point of reference I received Sperry (for JCrew) winter lines duck boots a couple of years ago which also only came in whole sizes and am trying to Guatemala whether I should go with my normal 7-or size down to the 6?

  23. I love both outfits, especially the Caslon boots, but that second outfit with the scarf is really calling my name! The scarf on the Nordstrom website looks a lot more orange-y, whereas in your photos, it’s toned down a bit. Which one is closer to the real colour? Thanks!

  24. I really like the sweater with the scarf… looks so good together. Can’t get into those style of boots though!!
    Congrats on your Nordstrom page!! 🎉

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