How to bundle up in style

Hello there! Happy mid-January to you. Popping in to give a brief update on how the year of less is going, and also update an old post from the archives of this blog covering a topic near and dear to my heart this time of year: how to style your outfits when you live in a climate of single-digit temps, snow, and slush. You know, the kind of place where it becomes socially acceptable to show up to social gatherings in marshmallow coats with snot frozen to your face, glasses fogged over, and pants that you've slept in (possibly multiple nights in a row). (I've been there… recently… so this refresher is for both of us.)

Ok, first things first: the YOL update! Two weeks in, and we're going strong with meal planning and have received only one Amazon Prime delivery to restock my Skinceuticals CE Ferulic serum. I've had zero temptation to buy anything, but we have run into a few questions around rules for the year:

  1. Are we going to allow ourselves a 'date night' budget that counts as social eating out, or does it need to be eat at home if it's just the two of us?
  2. Should we have more constraints around budgets for social eating out? After I went out to dinner with a girlfriend at an extremely hip, very expensive restaurant and we accidentally had multiple very expensive bottles of wine, Wes made the point that it would be easy to inadvertently shift our savings into overspending in other areas we're allowing for this year and it might be wise to hold ourselves to a cap each month.
  3. Do candles count as groceries? (I burn candles constantly, and they are important triggers for me to unwind, right up there with music and dimmer light switches.) My candle supply is going to last me until mid-February, so have a little time to think on this one.
  4. How should we handle birthdays? Allow for gifts, or contain it to experience-based investments?

If you have advice or thoughts on how we should answer these questions, please feel free to leave me a comment or shoot me a note.

Alright, on to the topic at hand for this post: how to avoid succumbing to the temptation of dressing like the Michelin man for the next few months. If you live closer to the equator or in the southern hemisphere, you can drop off here.

Figuring out how to style myself for an average winter day was challenging when I moved back to Chicago a few years ago. Learning how to invest in outerwear and boots was one part of the challenge, but figuring out some of the following questions took time for me:

  • What kind of pants do I wear with equestrian boots? Snow boots? Chelsea boots?
  • What kind of socks do I need to wear so they don't fall off in my boots?
  • Are there ways to style my clothes so I can avoid wearing tights?
  • What kind of coat do I need to wear with a dress? A tunic?
  • How can I layer myself so that I don't suffocate on my train commute?
  • How do I wear these leather leggings in a way that does not make me look like a dominatrix?

You get the idea. They sound funny when I type them out, but all of those questions have come up for me in the past as I tried to get dressed for the cold.

If you've been reading for a while, you know that I am big on planning out your outfits in advance in order to improve your style. You also may remember that I believe that all outfit planning should start with selecting the shoes (or boots) that will work for the various activities you have going on in a day. I know some people wear snow boots and carry extra shoes with them to change into at work or at a party, but for me that's too fussy and would introduce the risk of forgetting or losing my shoes.

Anyway, I am saying all of this because I spent one Sunday afternoon planning a few weeks' worth of outfits to avoid YOL boredom / temptation to buy, and decided to kill two birds with one stone by sorting through every single pair of winter-appropriate footwear I own and building outfits around every pair to have plenty of options for the various* activities I do during the winter.

Speaking of boots, this is a great segue to the first tip below - I hope you enjoy them all (and the reminder if you remember this post from back in 2015)!

#1 Collect boots that multitask 

Invest in boots you love that can be worn in a variety of settings, from hiking through slush to the train, to meetings at work and social events on the weekends. I ignored the over-the-knee boot and Hunter boot trends for this reason, because I didn't think they would get great mileage in my wardrobe. A great pair of black ankle booties with a pointed toe, a pair of flat boots in black leather that are roomy enough to be worn with Smartwool socks, and a pair of knee-high black rubber equestrian boots for really snowy days are really all you need. A few years ago, I also invested in a great pair of black suede mid-calf pointy-toed Sigerson Morrison booties that are the perfect high heel replacement for any outfit.

Since this was originally posted, I also added a pair of simple Stuart Weitzman tall black leather flat boots that hit just below the knee, and ended my search for a pair of boots with the comfort and utility of UGGs but chic. (The ones I bought were from House of Harlow 1960, pictured below.)

#2 Up the quality of your sweaters

I have a few amazing cashmere and wool sweaters (I love the brands Vince, ACNE and Eileen Fisher) in neutral colors (cream, black, gray) that are on constant rotation in my wardrobe during the winter. I've shown an oversize ACNE one styled a few ways in this post. After cutting out shopping for a year, I realized that I gravitated towards my sweaters that were super high quality, slightly oversize, and in neutral colors. After recognizing that, I made an effort to avoid anything that didn't meet those qualifications and developed a willingness to spend significantly more if I found one that did.

#3 Invest in a several simple-yet-wonderful coats

In cold temperatures, your coat sets the tone for your whole outfit and it's worth having a good selection that you can rotate. Over the years, I've invested in a few basics with timeless shapes (like a wool pea coat and a long blazer coat) and have used them season after season. You can also layer lighter coats to get more out of your collection. I should also note that I have a long down jacket a la sleeping bag that I use for purely utilitarian purposes like taking my dog out and other non-stylish events of the like.

(As an update to this tip, I decided to style my long down jacket with an oversize cashmere scarf, great shearling gloves and apres ski boots for an example of how to upgrade the basic leggings-and-UGGs when you venture out on the weekend! See below.)

#4 Use hats as a statement piece

For a really long time, I hated hats and convinced myself that they'd ruin my hair volume and make me look ridiculous. But they are absolutely essential to staying warm, so I got over it and have since built up a nice collection of cool hats that not only keep heat from escaping from my scalp but also add an element of cool to my winter outfits. I've got a Russian fur hat, a basic American Apparel beanie, a classic French wool beret, and a cashmere beanie that I rotate as accessories. When I started thinking of them as accessories, it changed everything. Where my 22-year-old self would think I look crazy in a hat, I think they lend my outfits an air of "I don't take myself too seriously" or just that practicality never goes out of style. As my dad says, it's impossible to be cold if you're dressed right. 

#5 Add an unexpected accessory

By unexpected accessory, this can be a pair of fun earrings, a vintage silk scarf worn as a bracelet, or a beautiful clutch that hasn't gotten enough airtime lately. Lately, I've been trying to mix in my 'summer' bags to freshen up the monotone, all-neutral looks I tend to wear this time of year.

#5 Mix and match your hats, scarves and gloves

I've built a small collection of oversize cashmere scarves in neutral colors (one each in black, gray, and cream) and love to mix and match them with my collection of hats-of-varied-textures referenced in point #3 above. Because my scarves and hats are so simple, they go with all my coats and add variety and a much-needed element of eclectic luxury for those days that I'm plodding through slushy, brown snow to the train. 

#7 When all else fails, wear red lipstick

My aunt recommended Armani Express Moisture lipstick a few years ago when I was complaining that my dry, chapped lips were interrupting my lipstick game. I picked it up in the perfect red shade called Rouge Ecstasy and it's changed my life. Even when there are tears frozen to my face, I feel stylish whenever I wear it. I wear it constantly and it lasts forever, and is worth every cent. However, if you cannot reconcile spending $40 on a tube of lipstick, Burt's Bees lip balm with a red tint does the trick as well and adds some much needed color to a simple-yet-very-warm outfit of all neutrals.

That's all I've got for you, hope you enjoyed this post and would love to hear your thoughts in the comments. 

*By various, I mean three activities, if we are not counting my homebody habits of sitting in front of my fireplace in my pajamas or in front of Wes's ginormous TV watching Netflix with a Costco-sized bag of SkinnyPop at the ready. (Which has been done more nights in the past two weeks than I care to admit. Old habits die hard, especially in winter.) Those three activities are going to the office, dining out with friends, or relaxing with friends via pedicure, Chinese massage, or sitting around someone's living room with wine and Cards Against Humanity.