If you’re anything like me, you find dressing for the cooler months challenging. I am a lover of layering, and it’s essential this time of the year, but piling on clothes often makes me feel sloppy. Yesterday I sat in a meeting in my down jacket. Today I kept my hat on inside. I want to stay warm, but I also want to look professional.
I am one of those “temperature sensitives” who chatters to the point of vibrating in the cold and, as Todd often says, “wilts like a dead flower” in the heat. The heat, however, is generally easier to deal with, sartorially speaking. It’s also cheaper to dress yourself in the warmest months. Sandals, wispy dresses, light cardigans…done! The summer is when I find myself purchasing more disposable (read: cheaper) clothing. The cold months, however, sometimes require solid investments. Sure, you can find some great deals on eBay and in thrift stores, but a decent coat is going to cost you and it’s generally more prudent to purchase a pair of boots that will not fall apart before the season is over.
I’d love to hear your winter weather tips and recommendations. In the meantime, I’ve taken stock of my closet and determined what items I need to help keep me cozy, and stylish, through April.
Proportions
I am 5’5″, slender, with longer legs and very little in the way of a torso or waist. I dislike tight clothing on the upper portion of my body and I can’t wear belts. I love the flattest flats and highest heels, but I prefer heels in the fall and winter.
The proportions that work best for me during the cooler months, as detailed below, are:
- Slim/skinny jeans paired with heels and a cropped jacket or boyfriend blazer.
- Mini dresses paired with a cropped jacket and boots/heels.
- Boyfriend jeans paired with a floaty top, jacket and heels.
Likes
- Vests. Big puffy vests or small, cropped decorative waistcoats, they all add an interesting proportion.
- Anything mini. My legs are my favorite body part.
- Scarves. I can’t get enough of them.
- Knit beanies. I think they look cute, especially with super straight or slightly wavy long hair.
- Croppy jackets. Not *too” cropped, but hitting just at the hip, especially if they are fuller. Paired with a longer top, it’s a good proportion.
- Jeans for work. In black, cord…anything but denim.
- Kimono or robe styling. Flattering on everyone, and comfortable.
- Ankle and wrist length pants and jackets. Anything with a higher hem doesn’t work.
Dislikes
- Long coats, with the exception of trenches. They swallow me.
- Belts. Love them in theory but they look like shit on me.
- Tight tops. They make me feel insecure and I hate enhancing my boobs in any way.
- 2/4 sleeves. Especially on a top that hits at the hip. They make my upper half look like a box.
- Trousers. Again, in theory, I love them. But I always feel dowdy when I wear them, even those with a great fit like Theory.
- Dolman sleeves. Cute, but hard for layering and always requiring adjusting.
2009 Fall Looks I Love

I’ve pulled together a selection of items for my favorite proportions as noted above. Items in bold are must-haves or great values. I love doing this, it’s a great way to get the shopping bug out of your system without spending any money!


- Tops – Mod Cloth Night in Dream City Tunic, $55; LNA Black Lace Tank, $84; Snug Nude Camisole, $36; Mike & Chris Cognac Dallas Lambskin Vest, $314
- Outerwear – Toki and Nabi Military Waistcoat, $64; BB Dakota Potter Vest, $68; Marc by Marc Jacobs Vera Cherry Peacoat, $172
- Bottoms – J Brand 7/8th Skinny Jeans, $185; Notify Night Blue Hellebora Capri, $128
- Shoes – Topshop Radar Edged Bind High Sandal, $135; Forever 21 Suedette Pumps, $10
- Bags – Tano Boogie Bucket Bag, $179; Rian Cross Zip Bag, $68; Hayden-Harnett Franklin Flap Bag, $545
- Jewelry – We Dream In Color Nyah ($34) and Arya ($28) Earrings; Funktional Chain Me Up Necklace, $50; Jack Rabbit Halcyon Earrings, $52; Lauren by Ralph Lauren Pearl Earrings, $24
- Accessories – Topshop Plaited Snood, $50; Topshop Chain Print Silk Scarf, $44; Tolani Zig Zag Stripe Scarf, $85; J Crew Skinny Calf Hair Belt, $40
Aubin & Wills Featured Outfit – Rebeck Blazer, $500; Madleigh Jeans, $200; Rayser Tee, $160; Ainsworth Belt, $80; Bowbank Snood, $240
Street photo courtesy of Jak & Jil, illustration courtesy of Garance Doré.


- Tops – Topshop Stripe Gold Button Cardigan, $50
- Jackets – Luella Tweed Military Jacket, $1,017; Topshop Snake Metallic PU Jacket, $125
- Bottoms – Zoé Fan Fan Tiered Mini Skirt, $145; Miss Selfridge Striped Tube Skirt, $30
- Dresses – Blush Button Dress, $130; Mod Cloth The Gilda Dress, $53; Forever 21 Heart Print Silk Dress, $27; Heritage 1981 Mini Checkered Rose Dress, $27; Hayden-Harnett Pandora Dress, $298
- Shoes – Topshop Dolan Over-The-Knee Boot, $170; Max Studio Zanzibar Bootie, $144; Forever 21 Chaz Suede Bootie, $25
- Bags – Topshop Double Quilted Cross Body Bag, $50; Marc by Marc Jacobs Totally Turnlock Percy II Bag, $198
- Jewelry – We Dream In Color Gem Earrings, $28; Forever 21 Textured Cascading Chains ($8) and Roxanne Satin Trim Necklace ($8); Susan Hanover Two Stone Wire Bangle, $55; Rachel Leigh Millies Bow Drops Earrings ($66) and Gumball Ring ($71)
- Accessories – Aubin & Wills Shortlidge Scarf, $240, AE Pointelle Tights, $13, Calypso Fur Funnel, $195; Hat Attach Knit Beret, $42
Aubin & Wills Featured Outfit – Meridith Short Dress, $200; Beloteen Tights, $60
Street photos courtesy of The Sartorialist and Mr. Newton, illustration courtesy of Garance Doré.


- Tops – Topshop Stripe Gold Button Blouse, $60; Marc by Marc Jacobs Fade Sweater, $174; Calypso Sequin Jersey Tank, $100; Delias Go Heart Your Own Tee, $27; Alexander McQueen Zig Zag Zipper Sweater, $321
- Jackets – Facoup Faux Leather Jacket, $65; Topshop Leather Square Bolero Jacket, $310; BB Dakota Medallion Jacket, $79
- Bottoms – Acne Generic Girl Ripped Jeans, $263; Gap White Boyfriend Jeans, $20
- Shoes – Forever 21 Urban Studded Bootie, $27; Chloé Strappy Leather Sandals, $300; Where Maxine Studded Wedge, $153; Seychelles Scallop Heels, $98; Miu Miu Suede Platform Heels, $555; Rupert Sanderson Patent Mary Janes, $920
- Bags – Tano Favorite Bookend Bag, $255; Hat Attack Plaid Tote, $82; Taos Beaded Clutch (No Longer Available); Kimchi Blue Metallic Hinge Clutch, $18
- Jewelry – We Dream In Color Talon ($28), Hummingbird ($32) and Blue Leaf ($28) Earrings; Forever 21 Suedette Trim Ring, $4; Hayden-Harnett Ramone Studded Cuff, $98; Jules Smith Silver Kiss Kiss Petite Necklace, $150; Adia Kibur Pearls Bib Necklace, $134; Forever 21 Bead and Mesh Necklace, $13
- Accessories – Gap Plaid Frayed Scarf, $25; Freelook Black Chrono Watch, $300; Ray Ban Classic Aviators, $135; YSL Rouge Volupté Lipstick in Red Muse, $34; Mod Cloth Wings of the Tiger Headband, $20
Aubin & Wills Featured Outfit – Rebeck Blazer, $500; Bramsby Vest, $180; Brenrin Straight Leg Jeans, $240; Glendurgan Travel Bag, $700
Street photo courtesy of The Sartorialist, illustration courtesy of Garance Doré.









{ 7 comments… read them below or add one }
I really like skirts and tights in the winter. Usually with cute boots of some kind. It’s surprising how warm tights can be. Although as I found out the other week when it was 17 degrees, lacy tights are NOT warm when filling your gas tank up.
Tangentially related, I buy jeans at Delias (I know, I know, but its cheap) and I just bought 2 new pairs on Monday, put one pair on tonight and realized they’re too low cut. I like the fit (skinny) and they’re the right size, but I think I’ve crossed a line where I’m just not comfortable in super low-cut jeans anymore, plus am I crazy or is the combination of skinny jeans and low rider really…not flattering? I don’t know maybe it looks better if you have slimmer hips.
Can’t wait to peruse all these links :)
Also, I recently got some cute sweaters from the gap. Just simple v-neck but I really flattering length and pretty colors.
Penny! I replied to you on Jezebel without seeing this post first, and now I feel like a weird copycat, because I basically wrote the same thing about disposable/summer clothes vs. investment/winter clothes; I’m also slightly spooked because now I think that you’re a mind-reader and know exactly what I’m thinking.
I love dressing for the colder months, and I tend to go in the opposite direction of my summer style, when I rarely bare my pale legs and I layer a lot. In winter, though, I go nuts with miniskirts and minidresses that I wear with tights of all kinds. And boots. I love boots of all types, so this is my season. I don’t layer much because I feel constrained, so I try to invest in as many cashmere sweaters and knit tops as I can (I find wool very annoying and itchy, and try to limit it to skirts.) And I accessorize a lot. Scarves, shawls, gloves, long necklaces, huge earrings. I just don’t wear hats (I have a big head!) , and I hate turtlenecks.
I love coats, particularly peacoats. And I don’t wear parkas (I’m short, and look awful in them).
I am always cold too! especially when I am sitting at a computer. my best solution? cashmere anything. while not exactly cheap, it’s soooo warm! I have purchased a couple of cashmere vests and short sleeved sweaters that I pair over button down shirts and wear with wide leg pants- I have the opposite frame as you, same height but long torso & a wee chest. I also think my toughest challenge in the colder months is finding shoes to wear to work- it’s already in the 20s here and I have a 40 minute walk in each morning, so I need something comfy and warm. I also really like the colors you use- often in winter, I find myself wearing all black head to toe, with my any color coming from scarves or jewelry. Gotta move to the west coast, I guess!
There’s cold, and then there’s COLD! We just came out of a deep freeze (-35 degrees celsius), and there’s at least a foot of snow on the ground – when it’s like that you have to resign yourself to looking pretty frumpy and “thick”. Heels would be treacherous, even on boots, and down is your best friend. Unless you park in a garage at all times, even the thickest tights won’t do!
But now it’s warming up and I can switch to a lighter coat, sweater and gloves! Things will be very slushy though, so waterproof boots are a must.
Ergh, I’m pretty bad at this proportion stuff. I have a tiny torso area and a randomly fat butt, so in the summer, I wear floaty, full ’50s skirts a lot. But in winter, I don’t know what to do. I’ve been wearing jeans every day with knee-length boots, but I feel a little stumpy (I’m 5’2″).
I think sometimes I try to wear “trendy” stuff even though proportion-wise it doesn’t make me look good. This post is a good wake-up call!
I have nothing to add except that I could read your styling tips all day. Well I guess I should add that during the “colder” months here in socal, I make good use of coats, jeans, scarves, and mini dresses and skirts paired with tights. I also recently got a pixie haircut and I am pleased with how cute hats look on me. :)