Gentri: Dressing for Winter Weather

Makeup artist, stylist and magazine founder Gentri loves everything vintage. She takes our retro Pillow Boots for a hike around her home state of Utah.

2 min read

We chat to professional blogger Gentri about dressing stylishly for winter weather, and the biggest fashion mistake she's ever made.

How did you dress as a child? What was your favorite thing to wear?

As a child, I lived in overalls and playsuits. Denim, velvet, corduroy, cotton; I loved them all!

There was one specific summer’s day where I wore a hot pink t-shirt and denim shorts. The outfit wasn’t really the problem, but rather my appearance. I was covered in ice cream and dirt, from head to toe, and specifically remember wanting to go home and clean up, before anyone else saw me in public!

“In the winter, my aim when getting dressed is purely based on comfort... Often that can mean not looking so hot, with mismatched layers thrown on in a hurry. So, lately, I’ve tried to make more of an effort to create winter looks I can feel and look great in!”
— Gentri

You have a time machine. What time and place do you travel to just for the clothes?

I would travel to anytime between the 1920s and 1940s. People knew how to dress, back then, and did it with such class!

“These new boots from Cougar have been my go-to. They are insanely comfortable, retro-inspired, have just a hint of red in the lining, and really kick up my winter outfit game!”
— Gentri

What’s the biggest fashion mistake you’ve ever made?

I used to wear this bright yellow, glitter eyeshadow, and had no idea how to apply it. Which meant it was covering my entire eyelid (lashline to brow). Once I saw a photo, and realized what a terrible mistake I’d been making, I quickly learned a bit more about how to apply makeup and ditched the glitter.

Related video

Watch: Cougar Shoes Fall 2018 Collection

What’s the biggest mistake people make when shopping for clothes?

I think people are too quick to purchase cheap, trendy, “disposable” options. Not that you have to have or spend a lot of money to look nice. But the saying “you get what you pay for” is very true!

I firmly believe in investing in just a few, quality pieces, rather than filing your closet with items you won’t like or be able to wear in a few months.

Who is your current style icon?

I am pretty much obsessed with Zoe Sugg (Zoella). I own a few things that I’ve seen her share, and would happily copy her entire wardrobe, if I could. Her style is classy with an edge, but has pops of color and quirky elements—which I love!

What’s the most important style item to invest in?

Shoes, for sure! Our shoes definitely do the most work, when it comes to our wardrobes, and there’s nothing worse than wearing a cheaply made pair of shoes that hurt your feet.

Check out Gentri's full Pillow Boot review and photoshoot on her website!

Gentri is wearing the Original Pillow Boot.

Photos courtesy of Gentri Lee.

Gentri's picks

Fargo Leather Ankle Boot

Colleen Natural Hide Ankle Bootie

Angie Leather Ankle Boot

Related articles

Ania: Rocky Mountain Boot Style

How does a fashion model keep warm in winter? Our natural hide winter boots are put to the test in the snowy Rocky Mountains.

Peri Natural Hide Winter Boot

Erica: #Warkit Stylist & Fashion Expert

Canadian stylist and fashion expert Erica Wark frequently shares style tips on CTV’s The Social, The Marilyn Denis Show, Etalk and Your Morning, helping women find their true style-selves.

Kensington Chelsea Boot, Vanora Suede Winter Boot, Dani Suede Winter Sneaker