What To Wear Where: October

My favorite month seems to be October and not just because my daughter was born this month. I love Halloween, pumpkin patches and just the smell that is in the air. After the high and low confusing weather that September brings, October truly feels like fall. It is also usually a relaxing time for me. Usually. This week has been a bit of a whirl wind and it doesn’t seem to be slowing down anytime soon. In order to be able to tackle the week, I have to preplan my wardrobe and honestly live in flats because I’ll be running around quite a bit. Here is my inspirational guide for what to wear where for October.

  • What to Wear | October 1 of 8
    PicMonkey Collage

    Need inspiration for this month? Check out my wardrobe plan for the week. 

  • Sunday | Family Day 2 of 8

    Sundays were made for family, a day to enjoy the best of the season. Sunday we enjoyed the pumpkin patch, corn on the cob and painting pumpkins later on at home. The weather was nice, it was sunny but it was in the lower 6o's and when the breeze it, it was crisp so I layered a vest over a sweater to keep warm and because it is the weekend, I had to wear my boyfriend jeans. I've been wearing more and more flat boots and these were perfect. I also made sure to take a small tote in case we ended up picking up a few small items. I kept the family on track because of course, I could never leave home without a watch. 

    Vest available at J.Crew, $108

    Sweater available at Dorothy Perkins, $29

    Jeans available at Mango, $70

    Boots available at Lulu's, $36

    Tote available at Sperry, $155

    Watch available at Asos, $54

  • Monday 3 of 8

    Monday is a "light" day. By light, I mean wearing flats again to go grocery shopping for the week, party shopping for my daughter's 4th birthday party and an afternoon play date. A pair of chinos and a plaid shirt keeps me casual but I've found a way to dress it up with a fur vest and hoop earrings. A cross body bag keeps my hands free for shopping bags and fits my phone, cards and my lip balm. 

    Shoes available at Asos, $75 

    Pants available at Jack Willis, $79.50

    Bag available at Target, $16

    Earrings available at TopShop, $20

    Lip balm available at Macy's, $3.30

    Shirt available at Mod Cloth, $40

    Vest available at H&M, $40 (UK site)

  • Tuesday 4 of 8

    Tuesday is an office day but since my little one is in school, I will be at the local coffee shop with my laptop and laptop case in tow. A stripe sweater and plaid flats are fun prints to mix especially with a vegan leather skirt. Black rimmed glasses and a brimmed hat makes me feel like I'm investigating something really next fall's trends. 

    Shoes available at Forever21, $16.80

    Sweater available at Loft,$29.50

    Skirt available at Pixie Market, $67

    Glasses available at Karma Loop, $18

    Hat available at Swell, $32

    Laptop case available at Leather Story, $98

  • Wednesday 5 of 8

    Wednesday is a busy work day. I need to carry a satchel for a morning meeting and want to look good for a fashion show in the afternoon. A little black dress is the perfect solution for both events and for running from place to place, a comfortable but fashionable pair of black boots. A watch ensures I stay on time, red lipstick means I mean business but a parka says I still keep it fun. 

    Dress available at Uniqlo, $59.50

    Bag available at Nordstrom, $68

    Jacket available at RALstyleShop, $60

    Boots available at Zara, $189

    Lipstick available at Lancome, $30

    Watch available at Sperry, $160

  • Thursday | Field Day 6 of 8

    I cannot wait for Thursday since my little one has a field trip to the fire station. Most women understand my excitement though my husband still gives me a dirty looks so I'll down play my look by dressing up a pair of sweatpants with a simple black top and a poncho. I'm not trying to look overly made up so simple eyeliner will be enough for the day as will a comfortable pair of lace up flats. A back pack for snacks and a small bracelet will finish off the look. 

    Pants available at Nordstrom, $88

    Top available at Uniqlo, $39.90

    Poncho available at Sperry, $48

    Eyeliner available at E.L.F, $3

    Shoes available at Amazon, $20.99

    Backpack available at Nine West, $39.99

    Bracelet available at Kiel James Patrick, $40

  • Friday | Work Event 7 of 8

    This Friday I have a fun event I am scheduled to work at one of the major department stores downtown. As a freelance make up artist, I've decide to only work only major events as I seem to be more and more pressed for time. A basic striped dress works well as long as I am wearing a black jacket to dress it up a bit. Adding leopard booties makes it fun and black tights keep me warm, it is Chicago after all. A classic lip color, a bold manicure and a statement necklace are the perfect finishing touches to my look. 

    Dress available at Forever21, $15.80

    Jacket available at New Look, $64

    Shoes available at DSW, $99.95

    Tights available at H&M, $12.95

    Lipstick available at Saks, $26

    Nail polish available at Julep, $15 

    Necklace available at Monsoon, $38


  • Saturday | Girls’ Brunch 8 of 8

    A crisp Saturday afternoon in October is the perfect time for girlfriends,  trench coats, statement necklaces and blood stained manicures. And if you plan on spending that afternoon sans little one(s), a clutch is all you need to carry your cards and a low heel bootie just so still feels a bit glamorous. Of course, any excuse is good enough to wear a dress but with the weather the way it is, I have to throw on some leggings to keep warm.


    Dress available at TopShop, $76

    Leggings available at Old Navy, $14.50

    Coat available at CiChic, $82

    Shoe available at C. Wonder, $148

    Bag available at Sole Society, $39.95

    Necklace available at New Look, $15.99

    Polish available at Essie, $5.99

Article Posted 3 years Ago

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