
Mad Men billboard on the subway at the 23rd St stop. Instragram photo from a few weeks ago.
Ever since I heard about Julia Bobbin’s Man Men Challenge I knew I’d definitely be in. I’m torn between making a straight replica or something heavily inspired by, but nevertheless here are some of the characters and outfits that have inspired me.
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(Source: Tom and Lorenzo’s Mad Men Style.)
Joan Holloway’s Black Dress
Pattern contender:

McCall’s 7488.
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Rather than make a straight replica, I want to do my own take on it. I actually don’t own a simple low-cut black dress with a pencil skirt, but it seems versatile enough and having out in my wardrobe seems like it would be a workhorse.
Pros:
- Basic dress, wardrobe staple
- Easy to make? (Ha! Famous last words!)
- Unique cut and pattern
Cons:
- Need to buy fabric for this one (Alright that’s not really a con, but I’m trying to be fiscally responsible here)
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(Source: Tom and Lorenzo’s Mad Men Style.)
Joan Holloway’s Pink Dress
Pattern contender:

McCall’s 4994.
I’ve already been struggling with McCall’s 4994 so I’ll probably use that as a base.
Pros:
- Pattern already adjusted, potential for a good fit very high
- Basic dress in a bright color
- Don’t own a dress like this yet, would wear it tons
Cons:
- This pattern was a nightmare to make (poofy sleeves?) but this blog is all about conquering your sewing fears and making it work
- Need to buy fabric
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Joan Holloway’s Purple and Pink Dress
The first time I saw Mad Men was on an airplane flight and this was the first episode I’ve seen, so this dress is particularly memorable to me.
(Source: Tom and Lorenzo’s Mad Men Style.)
Pattern contender:

McCall’s 4994, modified.
Pros:
- Pattern already adjusted, potential for a good fit very high
- Use fabric from stash
Cons:
- This pattern was a nightmare to make (poofy sleeves?) but hopefully at this point I’d have it figured out
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Kitty Romano’s Rose Print Dress
Pattern contender: self-drafted
Pros:
- unique pattern and fit
- I love flowers and would wear this year round
Cons:
- I have yet to scour the garment district thoroughly to find a fabric that isn’t truly vintage to match the rose print of this one
- Need to buy fabric
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Joan Holloway’s Rose Applique Dress
Pattern Contenders:

McCall’s 4994, modified.
Pros:
- Pattern adjustment already underway
Cons:
- No idea where to get roses to applique from (need more fabric?)
- Need to buy fabric for dress itself
- Do I have the patience to applique?
Nevertheless I really do like this dress and might attempt it in the future, just not for a sewing challenge.
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Midge Daniel’s Black Cigarette Pants and Blouse
Pattern contenders:

Pants: Simplicity 7886.

Blouse: Butterick 7886.
Pros:
- Both are wardrobe staples
- Both are flexible and can be worn year round
Cons:
- I have to buy fabric for the blouse
- Time restriction: I don’t know if I’ll be able to fit a pair of pants this accurately in 3 weeks and make a blouse on top of that
(I might do this in the future just without a sewing challenge in mind.)
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Helen Bishop’s Cigarette Pants and Blouse
Pattern contenders:

Pants: Simplicity 7886.

Blouse: Butterick 7886.
Pros:
- Both are wardrobe staples
- Both are flexible and can be worn year round
Cons:
- I have to buy fabric for pants and blouse
- Time restriction: I don’t know if I’ll be able to fit a pair of pants this accurately in 3 weeks and make a blouse on top of that
(I might do this in the future just without a sewing challenge in mind.)
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Verdict: My most favorite dress from this batch is Kitty Romano’s Rose Print Dress. My most favorite separates is Midge Daniel’s Cigarette Pants and Blouse. But the heaviest contenders for me in terms of time and practicality are Joan’s Pink Dress or Joan’s Pink and Purple Dress, so we’ll see how it goes.