Lumberjack Chic: What to Wear With LL Bean Boots

Winters are rough for fashion in Boston. From sweaters to snow boots, fashion choices are bulky and limited when you’re trudging through an arctic tundra. The LL Bean boots are the “it” boot in New England, but let’s face it, they’re not the easiest accessory to dress around. Put commuting to work via public transit into the equation and you’re left with either changing shoes every time you need to go outside or being lazy and rocking your LL Bean boots all day.

I’m obviously lazy and choose to rock my boots all day every day at work. I work at a startup where I have the flexibility to wear what I want (read: anything goes) but it was still important for me to be fashionable.

And so I faced a dilemma – how to make LL Bean Boots look good with casual work outfits.

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Doable, right? But it wasn’t that easy. Here’s the story. At first I had fun trying to make my popular and seemingly fashionable Bean boots look cute. I scoured Pinterest for outfit ideas and emulated them to the best of my ability. But as the days progressed into weeks, I realized that I needed to go off script if I was going to keep my feet warm and my ass from falling on ice.

back bay boston snow

I started experimenting, pairing different looks with my LL Bean boots hoping that I would find outfits that were more lumberjack chic than snow Yeti.

I paired LL Bean boots with layered Oxfords shirts, sweaters, and classic necklaces for a preppy look. This was my signature lumberjack chic look this winter. What you can’t see in the picture is the matching long underwear shirt and pants that made me feel all sexy warm underneath. I’m at least 5 pounds lighter than these pictures make me look thanks to long underwear layers.

oxford shirt sweater ll bean boots

I rocked the LL Bean boots with chambray shirts with cardigans and statement necklaces. When my jeans started falling down thanks to the silky long underwear, I broke down and bought some fleece lined leggings. I generally don’t wear leggings, but these were perfect for days when the comfort food proved to be too much for skinny jeans.

chambray cardigan ll bean boots outfitMost of my office worked from home on blizzard days, but I chose to brave the storm with my LL Bean boots, comfy boyfriend sweaters and cardigans, and long necklaces. These were the days I usually let my hair go wild for that sexy-windblown-by-a-blizzard look. I paired my fancy hair with my thickest wool socks and an extra friendly smile because I’m one of those freaks who gets excited by blizzards. Yes, really.

comfy sweaters and ll bean boots outfit

But the days came when I got sick of wearing boots and yearned for fun winter layers that would look cute with booties. On those days I threw caution to the literal wind and experimented with pattern mixing, pretending that I was wearing anything other than the clod-hopping Yeti-sized LL Bean boots. Desperate for any day other than winter, I even did my hair and makeup, hoping for some semblance of normalcy in spite of the feet of snow on the ground.

pattern mixing ll bean boot outfit

Warmer days, when the temperatures heated up to a balmy 20-something degrees, called for something flowy and spring-like. I mixed it up a bit, adding chiffon tops to the repertoire of valiant attempts to not dress like a lumberjack.

chiffon shirt ll bean boot outfit

At a certain point, I just gave up and embraced the insanity of winter. I even went so far as to pair lace tops and sweaters with my Bean Boots. I hoped that the dudes in jeans and hoodies at work wouldn’t notice the horrendous failure of mixing delicate lace with rubber-soled tumbled-leather boots meant for the Iditarod. If they did, they were nice enough not say anything. Thanks, guys.

lace shirt ll bean boot outfit

Today is another snowy day in the frozen tundra and another attempt at styling an outfit with my LL Bean boots. Do you have any favorite outfits with your Bean boots? Please share – I’m desperate for new ideas!

4 thoughts on “Lumberjack Chic: What to Wear With LL Bean Boots

  1. SMD says:

    I think you rocked those boots! Winter is hard though, choices for footwear and outerwear are limited. I often feel like I’m wearing the same thing. I think you did a good job of mixing it up!

    I need new winter boots next year. How do they do grip-wise in the city on snow/pavement?

  2. Caitlin says:

    Oh my gosh I’m in LOVE with the outfit with the polka dot top, as well as the lace peplum-y top. I just adore your sense of style! And I LOLed at “the literal wind”.

    • Emily says:

      Thank you so much – you know how hard it can be to feel cute in huge boots! There are only so many days that I can wear a button up under a sweater before J.Crew tells me to stop dressing like their male models!

  3. Kassandra says:

    Which LL Bean boots are you wearing in these pictures? Thank you so much for the style ideas. It helped me decided to buy a pair of LL Beans!

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