How To Be Comfortable And Stylish 0
in Style

How To Be Comfortable And Stylish

how to be comfortable and stylish

How to be comfortable and stylish. There are those days when I desperately wish that it was appropriate to go to work in my sweats and my faded baggy t-shirt. Sure, when I was still actively working as a fitness instructor I lived in sweats, but they were never baggy or old. As much as I cherish my Louboutins and skinny jeans and fitted moto jacket, when it has been raining for the umpteenth day and I haven’t been to the gym and I’m feeling bloated, the last thing I want to do is show off my body.

how to be comfortable and stylish


Layers. When the weather gets cold, we all love to layer and this is your perfect excuse to just that. Choose your favourite and softest tee, throw a great cardigan over top, pair them with a pair of dark jeans (they are more dressy than their lighter counterparts) and oxfords and top the whole outfit off with a menswear inspired coat. You’ll be right on trend and comfortable at the same time. Or, another great layering ensemble is a pretty dress topped with a cropped sweater. If you are going for this option, just watch your proportions so that you don’t look too sloppy.

Prints. Prints are great distractions, but they are also eye catching and will elevate any look. Opt for a printed blouse and skinny black pants (yes, with stretch as we are sill going for comfort), ballerina flats or ankle boots and you have a great look for the office.

Monochrome. A monochrome look is always sleek and sophisticated, whether you are opting for all black or your most flattering favourite colour, just make sure that your outfit isn’t pilling or over-sized. Choose tailored pieces that fit you and complement your shape.

Sneakers or wedges. Even though heels are usually dressier, a pair of sneakers can look pretty fabulous as well. Pair them with boyfriend jeans, a dress or pretty much anything in your closet.

Beanie or beret. Hats have a way of elevating any outfit, but sometimes that fedora or cloche just doesn’t feel right. So throw on a beanie or a beaded beret. Not only will it hide a bad hair day, but it will do double duty by keeping you warm.

Steal from the gym. ‘Cause sometimes you just need that extra bit of coziness in your life. Wear a hoodie in a soft luxurious fabric like cashmere. Pair it with a great lipstick, your favourite jeans and go about your day.

Accessorize strategically. Of course, I’m referring to a luxuriously over-sized scarf. Create a chic collar effect by wrapping it numerous times around your neck and shoulders, or wear it like a cape by wrapping it around your shoulders. Add some complimentary earrings and you’ll have a put together glam look in seconds. Plus you’ll be cozy and warm.
how to be comfortable and stylish

It’s totally okay to be comfortable (really, there’s nothing worse than leaving for the day wearing something that you are uncomfortable in, as you’ll find yourself fidgeting and tugging on your clothes all day) . What’s not okay is to look sloppy. Pay attention to fabrics, cut and proportions and when in doubt, show a little bit of skin.

What are your tips for staying cozy and stylish at the same time?

For more don’t forget to follow me on INSTAGRAM and PINTEREST


images courtesy of DollarPhotoClub



Caroline has worked with international designers in fashion retail and completed professional makeup courses when working in the beauty industry. Her love of writing, photography and film inspired her to work at the Canadian Film Center and then to earn a BFA in Screenwriting. In addition to her blog, Style On The Side, you can see her work in Huffington Post Canada and other international websites.

Latest posts by caroline (see all)

You Might Also Like

How To Wear Gray

Your 8 Rules To Shopping

How To Look Good In Tights

How To Wear Athleisure

How To Style Chunky Sweaters

How To Feel Good About Your Style

How To Dress An Hourglass Shape

Makeup Pouches In Style

Best outfits for winter travel

Cocktail Fashion: Drink, Dress and Ring

How To Choose The Right Accessories

Best Accessories For Fall

Designer Spotlight Quinoa Paris

British MODE December Issue

How To Pack For A Weekend Getaway

Why You Should Dress For Yourself

One Dress Three Weddings

Shoe Shopping In Madrid

How To Succeed Online Part 3

How To Look Effortlessly Chic

Crystals For Winter In Style

How To Make Your Legs Look Longer

Black… And the Colour is Gone…

Designer Spotlight Talk To My Shoes

10 Creative Ways To Style Up Your Office Outfit

Dance Inspired Wardrobe

Designer Spotlight Femi Pleasure

How To Add The 60s To Your Style

Fashion Of Anime Cosplay

Best Sweater For Your Body Type

Gift Guide For The Fashionista

Effortless Style And Beauty

Must Have Coats For Fall

Blogging And Living Abroad

European Style And Travel

How To Add Colour To Your Fall Wardrobe

Coach Bag Is Art: Style

How To Wear Sequins For Day

How To Wear Green For Spring 2015

What To Pack For A Mini Getaway

How To Style A T-Shirt

How To Look Less Frumpy

Fedora: Traveling In Style

When It’s Too Hot To Pick An Outfit

How To Be Casual But Stylish

How To Wear Flowers In Your Hair

Hair Accessories: Hair Raising Tale

Travel Style And Life

What To Wear On A Boat

Designer Spotlight Blackbird London

How To Style Flats

Top 5 Style Posts Of 2015

How To Wear Red 2013

How To Style A Polka Dot Dress

How To Wear An Oversized Tshirt

7 Bags Every Woman Should Own

How To Effortlessly Reinvent Your Style

Why You Have Nothing To Wear

What Your Watch Says About You

Vintage Shopping In Berlin

8 Tips For Packing Light

How To Dress Up A Boring Outfit

How To Find Your Style

How To Dress An Apple Shape

Style On The Road

Your Ultimate Wardrobe Color Guide

Portland Shopping Garnish Apparel

Style: London Fashion Week

Designer Spotlight Darylynn Eyewear

How To Buy Pants That Fit

How To Wear Purple 2013

November Favourites

Summer Road Trip In Style

How To Style Jewelry

Designer Spotlight Work Wonders

How To Wear Summer Whites

How To Dress A Ruler Shape

Be Stylish Not Fashionable Or Trendy

How To Dress An Inverted Triangle

Best Jeans For Your Body Type

British MODE: Haute Couture

How To Dress In Your 30s

Designer Spotlight Perfect Black Leggings

Make 2016 Your Most Stylish Year

Style: Lazy Summer Days

Military Inspired Style For Spring 2015

How To Be Modern Boho

How To Wear Pink

Summer Dresses In Style

How To Wear Orange Spring 2014

How To Succeed Online Part 1

How To Dress A Pear Shape

Is It Okay To Wear Nude Tights

How To Wear And Care For Velvet

How To Find The Perfect Party Dress

Shopping For Court Shoes

Monogram Jewelry In Style

Navy Heels With A Touch Of Gold

How To Wear Gold Jewelry

How To Wear Ankle Boots

How To Dress Just For You

Clothing Tips Every Woman Should Know

Why Is Style So Important

Designer Spotlight Konplott Jewellery

How To Wear Fringe For Fall 2014

How To Succeed Online Part 2

How To Buy Pearls

Statement Earrings Guest Post

How To Style Hats For Fall 2014

Sunday Musings In Style

Granville Island Artists

Photography For Bloggers Composition

Wedding Sparkle in Style

How To Dress For Summer

How To Wear Black

Interior Design: Style On The Side

How To Keep Your Clothes Looking New

How To Travel In Style

What Your Hat Says About You

How To Dress For Canada Day

What Your Sunglasses Say About You

Long Evening Dresses

Fashion Picks For November 2014

Designer Spotlight EverywhereUR

How To Wear Silver Jewelry In Style

Odd Pears Why Socks Matter

Jewelry: Salt Spring Island Style

Fashion Rings For Style

How To Dress For Winter

Best shoes for traveling in Europe

How To Style Sneakers

Pre-Loved: A Treasure Hunt At Holy Rags

How To Mix Prints In Style

What Your Jewelry Says About You

Should You Have A Minimalist Wardrobe

Unique Jewelry Fabulous Accessories

How To Wear Plaid For Fall

How To Dress Vintage Modern

How To Make Clothes Look Expensive

Best Summer Bag For Everyday 2014

Best Dresses For Summer At Fine Finds

How To Pull Off Hats

Stay Healthy And In Style In Las Vegas

Luxury in Style: September Celebrations

How To Wear A Moto Jacket

Best Way To Wear Sweaters This Fall

Are Sandals Bad For Your Feet

Your Shoe Wearing Guide

How To Travel With Your Jewelry

How To Take Great Photographs For Bloggers

How to Wear Mint

How To Add Prints To Your Wardrobe

How To Wear A Tshirt

Best Coats For Spring 2015

How Style Affects Our Confidence

How To Shop For Vintage Clothing And Bags

How To Make Heels Comfortable

How To Feel Beautiful

Ultimate Guide To Layering

Designer Spotlight SYCAMAW

Best Sunglasses For Your Face Shape

Dresses Every Woman Should Own

Style Stories Louboutin Heels

Summer Solstice In Style

Which Type Of Tourist Are You

The Eternity of Diamonds

Must Have Hats For Fall 2014

How To Choose The Perfect Heels

Fall Outfits That Will Always Work

How To Wear Pink For Fall

Best Pants For Your Body Type

December Style Picks 2014

Where to find Modern Artisan Jewelry

What Your Bag Says About You

How To Dress In Your 40s

How To Wear White After Labour Day

October Fashion Beauty And Fitness Picks

How to Walk in Heels In Style

Best 2016 Runway Shoe Trends

Jewelry Every Woman Should Own

Beret: A Hat For All Seasons

Off Duty Style

This Ain’t California: Skateboarding Fashion

What To Pack For A Long Flight

How To Wear Pastels Spring 2015

Where To Shop For Vintage And Designer Apparel

Sidewalk Sale Shopping in Style

Style Habits That Make You Look Older

How To Love Your Clothes When You Don’t

Links I Love

How To Add Colour To Your Wardrobe

Styling Tricks Every Woman Should Know

New Year: A Wonderful 2014 To All

Classic Pieces Every Woman Should Own

Summer Office Style

Essential Accessories For Men

Best Beauty Products For Spring 2015

How To Store Winter Clothing

How Where You Live Influences Your Style

How I Lost My Style

Womens Essential Checklist

Contemporary Fashion Georgie And Elaine

Shopping FAQ In Style

How To Take Your Wardrobe From Winter To Spring

The Truth About Heels

Glasses: Blink and you’ll See!

Must Have Spring Accessories

Vintage Bags In Style

How To Update Your Wardrobe

Best Shoes For Travel

Patches of Denim

Buying Jewellery: Must Read Tips

White For Fall In Style

Best Gifts For The Fashion Lover

British MODE: January Issue

How To Wear Brown

How To Wear A Summer Scarf

Fashion Is Art In Portland

Style Picks For February 2015

Today We Wear Black

Eyeglasses For Everyone: Warby Parker

Designer Spotlight Best of 2014

Designer Spotlight Standfor Shoes

Polette Parisian Eyewear

National Hat Day 2014

How To Wear Sneakers With A Skirt

What Is The Deal With Loving Your Body

How To Wear Yellow

Best Hat For Your Face Shape

How To Look Chic At The Office

How To Dress When You Work From Home

How To Take Your Look From Day To Night

How To Determine Your Body Shape

Style Shopping at Fine Finds

How To Add 50s Style To Your Wardrobe

Must Have Statement Jewelry Fall 2014

What To Wear To An Interview

British Mode June Edition

What To Wear At The Pool

Fashion And Architecture

Ultimate Accessories Guide For Major Social Events

Everyday Bag Essentials

I Want To Be Her: Book Review

Fly And Fierce Boutique

How To Wear Green 2013

What To Wear When You Have Nothing To Wear

The Bespoke Tailor: A History Of Style

How To Dress For A Work Party

Date Night Essentials

How To Add 40s Style To Your Wardrobe

Style: British MODE

What Clothes You Should Splurge On

Arm Candy Show Off Your Bracelets

How To Be Elegant Every Day

How To Grow Your Blog With Pinterest

Must Have Statement Pieces

How To Shop For investment Pieces

Packing For Two Weeks In Europe

How To Wear Mixed Metal Jewelry

Essential Wardrobe Checklist For Men

How To Be Modern Gothic and Rocker Chic

Easy Rules To Looking Your Best

Consulting For Online Success

Your Go To Outfits At Any Age

Shoes Every Woman Should Own

How To Add The 70s To Your Style

How To Layer Clothes For Fall

British Fashion: How Do You Define It?

On Our Radar March 2015

Shopping In Portland Accessory Style

Top Summer Essentials 2014

9 Accessories Every Woman Should Own

How To Wear White

How To Wear Navy In Style

Must Have Accessories For Fall

Best Winter Accessories

How To Wear Dresses For Fall

How To Wear Cufflinks

Best Bags For Summer Sightseeing

Style For Research: Fascinator

Summer Dressing Guide

Branding And Images

Fashion Must Haves For January 2015

How To Style A Denim Jacket

Stories From The Road in Style

Am I Too Old To Wear That

Fashion Flashback Styles of 2013

Best Jewelry For Summer 2014

My Story In Brief

Look great this summer without being a hot mess

How To Make An Old Coat New Again

The Color Guide

How To Wear Scarves In Style

How To Wear Hats In Fall 2016

How To Choose The Bag For You

Ankle Boots Were Made For Walking


  1. Layering is my fav trick to stay stylish&comfy (and warm if needed:)))


    1. Me too or just throwing on my favourite cozy sweater. Thank you!

  2. Thank you for the useful tips dear Caroline! Baci, Coco et La vie en rose fashion blog – Valeria Arizzi

    1. My pleasure, thank you for stopping by!

  3. I love the monochrome tip! I usually go with lots of black and belted knit sweaters.

    1. Thank you! I stick with black too….

  4. Wouldn’t it be great if we could go to work in our sweat pants when we’re blah or bloating!lol I love to layer during the winter because I’m always cold. But on days when I’m feeling bloated my saving grace is to wear jogger/sporty pants. They’re super chic and so comfortable 🙂

    xo, Jackie

    1. Awesome tip thank you! It’s funny because even when I did go to work in my sweats they had to be very fitted to show off my body… it wasn’t much better.

  5. Interesting stylish tips!!!!!!!!!!!!!
    Kisses, Paola.


    My Facebook

    1. Thank you!

  6. lovely tips!♥ I’m obsessed with sneakers at the moment!:) they are so comfy and trendy at the same time!

    1. I agree! I love a good pair of sneakers.

  7. hi Caroline, these look amazing, nice trends
    would you like to pass from my blog?
    I wish you an happy day
    a big kiss
    <<< fashion blogger >>>

    1. Thank you so much! Of course I will stop by.

  8. thanks for the tips Caroline, I learned something new here 🙂

    Jessica |

    1. Oh I’m so glad, thank you for stopping by!

Comments are closed.