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Style Wardrobe Help: Working on a farm but with a few social fundraising events

A reader wrote in to say that she’d appreciate some guidance and help in figuring out what to wear for her lifestyle:

I am going to be working on a farm , in the near future.

I will be tending animals, building things, digging in the dirt. This will be in Kentucky, so the seasons are defined  but they also vary from hot to cold at times.

I do not go out on socially much but I will be going to fundraisers and be in front of committees, to present our presentations to raise money for our programs for  veterans.

I have been searching the web to try and figure out what I would need for my lifestyle, but can’t find anything that is very helpful for me.


Working on a farm will be dirty work. You do not want to wear nice jeans out to a farm and think you can repurpose them for a fundraiser without a problem.

You also don’t want to be thinking: oh my goodness I’m digging in a $150 silk shirt and it is going to get ruined!

That’s just nonsense.

So.. I propose two wardrobes.

One for working out on the farm with clothes that you can stay warm in, and get dirty in without worrying, and another for fundraising committees. Just a few choice outfits for this formal event (without being black-tie) should do the trick.


Now, if I were going to work on a farm (which would never happen in a million years because I am not an outdoorsy person and have never even gone camping), I would want to bring things that I am comfortable in.

Screw looking TOO cute, I’ll settle for being warm and comfortable.

Please keep in mind that I have zero experience with working on a farm, and sadly, all I am going to recommend is from knowledge I have pieced together from watching movies and reading books.

So don’t laugh at me.


  • 7 various tops: I’m imagining you’ll sweat a lot and get dirty and may need to change each day as you are not going to do laundry daily and wear dried-out-sweaty tops…
  • 2-3 toppers: I am thinking plaid flannel shirts, anything that is a light sweater or topper you can pull over your tops to stay warm but not TOO warm
  • 4-7 pairs of jeans: Again you won’t be doing laundry daily but if you’re OK with wearing dirty bottoms two days in a row, go with 4 pairs. I like jeans that are cheap for this purpose so you won’t care if they get ruined. The slimmer variety (skinny or straight leg) would be preferable so you can tuck them into boots.
  • Rainboots: Need this for the wet mud and rainy days; I love me some dry feet.
  • 2 pairs of solid shoes: I don’t know what this entails but I am imagining sneakers for warmer weather because I cannot imagine ballet flats being practical on a farm. I’d want to have 2 pairs to have 2 options just in case one pair gets filthy. Nothing in white please.
  • 14 pairs of socks: I like the feeling of dry, clean feet and if I get dirty or get my feet wet, I want an option to swap out mid-day.

So what does it all look like?

Various tops

Comfortable, 100% cotton would be my suggestion.


Again, comfortable, natural fabrics so that you feel good wearing them.


Inexpensive jeans can be had for $50 or less! Or you can spend a bit more, but whatever it is, be comfortable.

Rainboots & Solid Shoes

Must haves.


Whatever is above, PLUS:

  • 4 sweaters/jackets: Fleece jackets to keep warm, woolly but comfortable sweaters, anything in a darker neutral shade is preferable to lighter colours
  • Winter jacket: This is to wear over your layers. I am used to sub-zero temperatures so I layer like mad under my winter jacket.
  • Winter boots: Need this for the wet mud and rainy days; I love me some dry feet
  • Winter hat and gloves: Enough said. Even with a hood on my jacket, I wear a hat underneath to stay warm.
  • 14 pairs of wool socks: Whenever I am out in winter in Canada, no matter if my winter boots are super warm, I NEED WOOL SOCKS. I also like changing my socks mid-day if I walked a lot in them so that I have a fresh pair for the afternoon/night and I feel good.

Note: Your rainboots can double as winter boots if the weather is warmer than sub-zero because you just wear wool socks inside and you’re golden.

So what does it all look like?


I like natural fabrics in sweaters or jackets, and polar fleece to keep warm and cosy is a plus.

Winter Jacket

A good, strong, down-filled jacket to stay warm and dry.

Winter Boots, Hats, Gloves and Wool Socks

Key words: Warm & Dry.


So now that the farm wardrobe is taken care of, I’d want a ‘nice’ wardrobe.

You don’t need much, just 3 neutral outfits and a few accessories to change up the looks.

I don’t know what you like to wear (separates or dresses), but I’d have at least the following:

  • 1 wrap dress: Not necessarily in a solid colour nor black; but something casual yet chic
  • 1 skirt: A nice skirt can do wonders if you don’t want to wear a wrap dress again
  • 1 trouser: Or if you prefer trousers, take 2 trousers instead of a skirt! A crisp, sharp pant can do wonders.
  • 3 various tops: To mix and match between the bottoms…
  • 2 toppers: To wear over your shoulders
  • 1 nice wool jacket: You can, but may not want to wear a thick, work winter coat to a nice gathering over your elegant outfit
  • 1 nice cashmere scarf and pair of gloves: You’ll need it to stay warmer and I like the huge blanket cashmere travel scarves because they can double as pashminas instead of a jacket or be worn as a scarf with said jacket
  • 1-2 pair of flats: If you want to do double-duty, get a pair of DRESSY flats which are of the pointed toe variety rather than a rounded ballet flat. Or if you want, have one dressy flat and one casual flat for stuff that isn’t quite so formal
  • 1 pair of heels: …that you can walk in. I like dark brown leather, no suede (too finicky to take care of) and no black if you can help it although it depends on what your preferred colour palette is (mine avoids black).
  • 1 pair of flat knee-high boots: This is just in case you want to wear any of the above out socially but not look too dressed up and look a little more casual. Or if you hate heels, get heeled knee-high boots. They look GREAT, are easier to wear for someone not used to wearing heels, and you can wear up to 2″ without feeling like the heel will fall off.

So what does it all look like?

Wrap dress

A neutral, small-ish print, and something knee-length, covering your shoulders.


Pencil or A-Line, take your pick and make sure it hits your knees for maximum longevity.


I like a crisp trouser in a bootcut or a skinnier crop cigarette-style one, either one looks good in heels.


I’m a sucker for silk, but any material will do as long as you are comfy and your skin can breathe in it. Rayon is nice for the summer… I’d also suggest covering your shoulders, no spaghetti straps that you’d have to cover with a blazer or topper.


Go casual (moto jacket) or more formal (blazer). The fabric of the topper matters too, wool is heavy and more formal, jersey is more casual and light.

Wool Jacket

A nice, stylish one for the cooler weather fundraisers.


I love a good blanket scarf for cooler weather, it doubles as a stylish pashmina in a pinch.


Pointed toe is more sophisticated than a rounded toe, and lace-up flats are really on trend right now. If you want to go classic, you can’t go wrong with a pointed, neutral beige/blush/nude flat.


If you wear them that is. I like 3.5″ as a comfortable height. I’d go for all leather, not suede, no platform front and either a pointed or almond toe heel.


…but if you HATE heels or can’t wear them, try a heeled boot!

Obviously a pointy toe with a stiletto heel is dressier for those fundraisers (first row), but if you want to go more casual, a chunky heel that is knee-high or even ankle-height is very chic (second and third rows).

Plus.. they’re great for going out and being social. You’re going to want to go out eventually!

That does it for my recommendations.

What do you think? Am I off the reserve?


  • Kim @ Needing The Dough

    I would consider substituting a pair of work pants for one of the pair of jeans. Work pants are much more durable, and may be more suitable for certain tasks around the farm (depending on what you’re working on) – the kind that Chiara mentions in #3. They’re expensive, but they can take a lot of abuse and still come out whole on the other end,

  • Cassie

    Erika covered most of the main points I would want to modify here. Work boots, or in a pinch taller hiking boots, are a must!

    I would take a jacket with a canvas exterior over one with a synthetic fabric for durability. I’d expect a typical winter coat to get snagged on stuff when she’s working, and then it’s completely ruined. Finding one with a zip out flannel or quilted liner will help take her through multiple seasons.

    Ditto on the gloves. She’ll want to get leather work gloves rather than quilted mitts. Depending on what she’s doing she may need to use her fingers to get in and out of pens and the barn, and the technical sports fabrics won’t protect her hands when she’s working.

    Long underwear are a must in the cooler temperatures. It’s all about the layers, especially when you’re working up a sweat and may need to remove a couple transitioning between the barn and other areas.

  • Chiara

    Hey Sherry, what a fun post. I’m thinking I should write you to ask for wardrobe advice for my life.

    I currently live on a farm and have spent a lot of time working on farms before. I think you’re pretty bang on with the two separate outfits category. The only extras I would add:
    1) avoid jeans with too much added plastic (Lycra, spandex, etc). If you can get 100% cotton jeans (which are really really hard to find for women) pick those. They’ll hold up to abuse a lot better than stretchy jeans. (Mine never tear in a cute place, Like at the knee, they tear on the inner thigh, which makes them useless).
    2) wool, wool, wool for winter. A chunky wool sweater is a must for the winter. They stay warm even if they get wet (from rain, water or sweat). Wool socks are good for winter, but my husband wears wool socks year round, because they stay comfortable even if your feet sweat in summer.
    3) I would strongly recommend you don’t spend a lot of money on new work clothes unless you’re getting clothes designed for heavy work (think carhart pants). You’re clothes will be ruined by heavy outdoor work to the point where that’s all they’re good for. Repurposed clothes you have that you’re thinking of donating, and hit up the thrift stores.

  • Erika

    As someone who has worked in an environment very similar to that of your reader, I can say that you did a pretty decent job. I will add some tips that I learned from my experience as well.

    1. Rubber boots for when it rains
    2. Work boots for everything else (I prefer a pull on style with crepe soles because they’re super comfy.
    3. Long johns are a must, possibly a silk pair because Kentucky gets cold.
    4. You’ll want a minimum of 7 pairs of work jeans. Buy whatever is cheap and comfy.
    5. Lots of layers. Tank tops, long sleeve t-shirts, hoodies, windbreaker, heavy winter coat (something similar to a Carhartt).

    I do not recommend sweaters or anything that has fleece on the outside (fleece liners are fine) because hay and debris will stick like Velcro. That’s why I prefer coats with a smooth or windbreaker materiel.

    Also, love downfilled vests because they keep your core warm while freeing up your arms.

    Starched jeans and a monogrammed polo/button down blouse may be perfectly acceptable depending on the location.

    Otherwise, the advice Sherry has written is a good start though you may want to pare it down a bit. You could choose one dress or a skirt, trousers, and blouse.

    If I think of anything to add I will.

    • Erika

      Wanted to add that I don’t recommend sneakers for farm and barn work. They don’t protect your feet or keep them dry and for some reason they pick up smell. I have worn trainers around the farm, but they typically end up needing to be washed because of the smell.

    • save. spend. splurge.

      THANK YOU! 🙂 I really appreciate the help.

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