Yet Another Winter Boot Trend to Jump On

January 15, 2019

OUTFIT #1: Combat Boots: Zara, similar here | Check Blazer: Vintage (my Uncle’s Versace, ha!), similar here | Mom Jean’s: Everlane | Belt: Vintage Gucci, found it in orange & also in gold (at a killer deal!) | Turtleneck: Everlane (more ways to style it here) | Bag: Italy purchase, similar here | Lipstick: Bobbi Brown

My first ever pair of combat boots was in the 5th grade (appropriate given it was 1999 – F, I’m old). They were a pair of brown Docs with a square-ish toe…I sold them on eBay a couple years ago and I feel the tears welling up just thinking about it. They were in mint condition and I could have had myself a nice pair of vintage combat boots. Sigh. Sulking in my sadness, I purchased this pair from Zara last winter. Not nearly as cool, but they will do.

LESSON TO BE LEARNED – things come back in style, they always do. Even the most heinous items that you could NEVER see yourself wearing again…if they’re good quality pieces, hold on to them for dear life.

Anyway, the whole point of this post is not to dwell on the eBay sale that took place (and also took a piece of heart), but rather that the combat boot, the 90s grunge staple, is alive & well.

How does one style one of the IT boots of the season? There are two ways I like to do it.

the tomboy look.

I’ve been a tomboy my entire life – clearly, at least since 5th grade with me & my Docs – so this look is totally in my element. When paired with a pointed toe boot, this look would appear more feminine and slightly formal. When paired with a combat boot, it leans more on the masculine side.

The blazer I have on here is (funny enough) my Uncle Johnny’s from the late 80s. It is masculine, quite literally. Thanks, Uncle J! I’ve officially added it to my growing blazer collection. It’s on the larger side, so I belted it to show my waistline (yes, I do have one under there). I added a turtleneck underneath, because ya know, that’s what I do lately.

I’ll call this look tomboy chic, and it can virtually be worn to any casual occasion or to a neighborhood bar for Friday night drinks. It’s the easiest way to style this type of boot. A solid combat boot look that will take you from a night out to brunch the next AM (although, please don’t actually do that, unless you had like a REALLY good date the night before…then all is forgiven).

a little ladylike.

As previously mentioned, I don’t really do uber feminine looks, at least not well. I’d consider this outfit about as feminine as I come. Sometimes, combining conflicting pieces can be a good thing – as in this case, a masculine pair of boots pairs well with a denim midi skirt, a frilly fur vest and lots of gold accessories. The best outfits I’ve worn with combat boots are ones paired with feminine pieces. I’m talking wrap skirts, flowy dresses, slip dresses, pleated midi skirts.

If you’re looking for a more adventurous approach, pair the combat boots with an unexpected, feminine piece. You’ll be the most stylish person in the room, promise.