Fall/Winter Fashion
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An Easy Way to Wear Combat Boots Into Spring

Happy hump day, friends! Today I’m sharing a transition outfit that features an easy way to wear combat boots into spring.

If you’ve been following my Try-On Hauls, you may know that I picked up these military-inspired Vince Cambria lace up boots a couple of weeks ago, and I was debating about whether or not to keep them.

Combat boots are definitely on trend right now, but they’re also a classic you can keep in your closet for years. Even so, they’re pretty rugged for my personal style aesthetic, and I wasn’t sure if I’d get a decent cost per wear.

I didn’t want to fall for a trend at the end of the season and find them sitting in my closet all next winter, but I’ve always kind of liked a menswear-inspired shoe. I still remember buying a pair of black oxfords in college and thinking they were so cool. (It was the 90s… go easy on me!)

Well, the 90s are coming back around again. I couldn’t believe it when my 15-year-old daughter mentioned wanting Doc Martens for Christmas. My mom surprised her with a pair, and she wears them constantly.

When I brought these home from the mall, I thought for sure she was going to tell me I was trying to look too young, but she actually loves them on me. I feel like they’re just a little more elevated than Docs, which is in keeping with my personal style.

There are definitely lower priced options out there that I could have considered, but these particular boots are pretty much made for my feet. The quality is amazing, and they’re extremely comfortable right out of the box — typical of Vince. (FYI, I sized down to a 7.5.)

So I did what I do when I’m unsure about a purchase, and I let them sit in my room for a while. As I put together outfits throughout the past couple of weeks, I would try them on occasionally, and they really are more versatile than I thought.

Here’s one I really like, with a camel cashmere turtleneck (size up) and my Gap sherpa hoodie (TTS; currently marked down to $29.99!)

I decided that I’ll be really glad I have these over time, and they actually work pretty well as a transition shoe here in Philly, where we can have cold and messy weather well into April. I won’t want to wear my snow boots and other winter styles that long, but I can continue to wear these.

As an added bonus, they’re weather resistant! Not that you can’t wear regular leather boots in messy weather, but when you spend this much, it’s nice to know these are made to withstand such conditions.

The only thing holding me back at that point was the price tag. I would usually wait for a sale, but I wanted to style them for the blog this month… so here we are!

By the way, these boots also come in a really pretty Cobblestone Suede if you prefer a softer look.

I also found a very similar pair by Sam Edelman at a more accessible price point. It even has the side zip, so you don’t have to tie and untie your laces every time you wear them, and I really like the croc effect detail up the back.

I’ve also heard great things about the Coach Lorimer lace up boots, and Frye makes a nice looking pair as well. I linked up those and more below, in case you’re shopping for combat boots right now.

Shop Combat Boots:

Combat boots work with a lot of different denim styles, and I’ve even seen them styled with dresses, but skinny jeans or leggings seem to be the most obvious pairing.

I like mine best with my off-black Good American skinnies. (This pair at Bloomingdale’s looks similar, at least the measurements are the same.)

And since combat boots have a masculine vibe, I like to incorporate a luxe or feminine piece, such as cashmere sweater. They also work really well with a sporty element because it’s in keeping with the casual aesthetic, but it still provides that juxtaposition that keeps an outfit interesting.

This cashmere zip-up hoodie is both luxe and sporty, and I really like how it offsets the toughness of the boots. It’s from Quince, and the price is very reasonable for Mongolian cashmere. For size reference, I have my usual small.

Yesterday we talked about elevated hoodies being a big trend for spring 2021, and this one will definitely be a staple in my spring wardrobe.

I wore it over a slub scoop-neck tee from Banana Republic, which doesn’t appear to be available anymore in white. Everlane has a similar one. I really like the scoop neck under the zip-up cardigan, I feel like it’s a very flattering neckline.

This shoulder bag is my Everlane Studio Bag, and I’m still bummed that it sold out so quickly. I’m a huge fan of bucket bags and hobo style bags for daily use, and this is such a nice everyday size.

I’m also wearing a pair of cat eye sunnies with glossy black frames. Sunglasses always make an outfit look more chic!

Mine are a Gucci pair that came in a Trunk Club last spring, and Diff has a nice polarized option for under $100. I also saw this Amazon pair recommended by another blogger, and they look pretty good for $15!

This neutral, almost monochromatic color palette keeps the look elevated, and I think it also complements the tougher vibe of the boots.

I played around with tucking my jeans into the boots and leaving them out, but they’re not quite long enough to tuck seamlessly, so I did a tiny cuff and wore black socks. That way, they don’t draw attention if they show a bit when I’m moving around; and it keeps a cohesive column of black on my lower half, which is elongating and slimming.

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28 thoughts on “An Easy Way to Wear Combat Boots Into Spring

  1. I remember when the combat boots were popular in the 90’s. I wanted to have a pair but i never felt right in any I tried on. Then I found a pair of black leather Capezio lace-up boots that were more feminine and I LOVED them. I kept them for 10 years after going out of style, hoping they’d come back. Guess I should have waited 20!

  2. This is a great transition outfit on you!  I envision you wearing the cashmere hoodie cardigan a lot, except during the heat of the summer.  Stay warm and have a great day!

  3. Love, love, love this look! The scoop neck T is such a minor detail but it really makes a difference. How is the quality of the cashmere on the hoodie? I think I’m going to order it as I am just not a cardigan girl– I’ve tried– but I love a sweater hoodie. And I am still seriously considering the Vince combat boots. I can see me getting a ton of wear out of them. I find that as I get older, I’m leaning into the styles I love that make me feel good.
    Thank you for sharing this outfit, Jo-Lynne. It made me smile!

  4. No combat boots for me ….not in my retirement community lol
    But cashmere sweaters you hv recommended best purchases of this year!! Perfect for all our cold weather!

  5. I like this outfit, especially the zip hoodie but it seems more like a fall outfit than spring? Because our winters are mild (well except this one) I don’t feel combat boots would be a good investment for me.  But my daughter has Dr. Martens and loves them and they worked out well in all this snow we’re having. We’re now going on our 3rd day without power. Weather wouldn’t be so bad if we could still function with electricity and water. 😞

  6. This look is definitely you. In the 90’s I had a pair of brown combat-style boots that had a plain heel, not the lug heel. I have never really liked the black combat boots—they just are a little too masculine for my aesthetic. I did buy the gray suede Vince Henderson boots, and they have the lug heel, but the gray makes them seem less masculine, plus, of course, the slip on style over the lace-up.  I think also it’s the black leather as opposed to the black suede. Everyone has their own preferences. 
    I have an old, old zip gray hoodie that was my husband’s when he was a young teenager. I immediately appropriated it for myself. Over the years, it shrunk, and fits me like your cashmere hoodie today fits you. I wear it to the gym in milder weather, and at home sometimes. It has to be at least 50years old, as he is 64 now.  It’s much older than anything else I wear, but I still love that thing, and part of it is that it was my husband’s originally. Anyway, that was my first thought when I saw your outfit. A cashmere, close-fitting hoodie is something I would definitely wear!  Love it!

  7. My tween asked for and got Doc Martins for Christmas. She wears them to school with her uniform and they are actually pretty cute with the feminine kilt. I don’t wear a school uniform, obviously, but may just have to borrow the boots this spring and play around with them. I think that they would be cute with light wash straight cropped jeans this spring. 

  8. Yay! Thank you for linking to the amazing cashmere hoodie. Just got it in black & I’m very excited! Love that they are a sustainable company too. Thinking about combat boots – I’ll have to sit with the idea a bit. I like the elevated look of yours. Thanks, as always, for keeping us stylish Jolynne! 😁

  9. This is a great look on you and is just my style. I ordered the cashmere hoodie and I can’t wait for it to arrive so that I can pair it with my black combat boots from the 90’s. I’m SO glad that I kept them for all of these years. 🙂
    Love your style Jo-Lynne!

  10. I have a pair of black leather Timberland boots that have the combat look. I even wear them in the summer with casual shorts when walking in the woods. I just leave a little sock showing above the boot. 

  11. Love the look!

    I bought a pair from Target.  I wasn’t quite willing to commit.  The faux leather has held up well and the shoes are surprisingly versatile.  I love them with skinnies (yeah, yeah) and rolled up straight jeans. 

  12. I love your sense of style. It incorporates a newer trend with a credible translation.
    Thanks for that. We all want to look current AND appropriate.

  13. Love combat boots! I’ve been needing a new pair and would LOVE the Paul Green Eva Combat boots, but at $485, I finally got tired of waiting for them to go on sale, and ordered a pair of the Ugg Noe moto boots. I also love that grey hoodie…will need to check it out. How do you think it compares to Naadam quality?

  14. I have a pair from about 6 years ago, that I still wear, as they’re good for cruddy weather days whilst on the playground.  They can take some wet and snow.  I really like these on you, Jo-Lynne, I have a quirky friend who has worn them with skirts and dresses forever.  

  15. Y’all are talking about wearing combat boots in the ‘90s — I wore them in the ‘80s 😳 In the 90s I was wearing platforms. I bought my current pair of combat inspired boots 3 or 4 years ago. They are super versatile and I wear mine with midi and maxi dresses as well as pants and leggings.

  16. Just wanted to let you know that I bought the Quince hoodie in black and I can’t believe how much I like it! It felt a little odd to spend so much on a black hoodie, but I do feel “leveled-up” when wearing it vs a hooded sweatshirt. And it’s nice and warm. Wore it around today (very windy, 35 degrees) with just a vest over the top and I wasn’t cold at all. I also went with the small and it’s a nice fit. (I usually wear medium in sweaters). Great recommendation.

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