• Skip to main content
  • Skip to header left navigation
  • Skip to header right navigation
  • Skip to after header navigation
  • Skip to site footer
  • Facebook
  • Instagram
  • YouTube
  • Home
  • Blog
Life In Pleasantville

Life In Pleasantville

Food, Travel, Life

  • Work With Me
  • LinkTree
  • Travel
  • Food & Drink
  • Living

Cottage Style: Transitioning from Weekday to Weekend with Ease

by Candace Sampson

With June well under way, we have unofficially started summer and also cottage season! But how to go from weekday to cottage weekend in style? I’ve got five cottage style pieces that will work with items you probably already have in your current wardrobe, to help you transition effortlessly.

cottage-style

Denim Shirt Dress

A denim shirt dress is one of the most versatile wardrobe pieces to have.

Work Style: For a casual Friday belt it for a more polished and structured look and pair it with tan coloured platform sandals or shoes.

Cottage Style: When you’re heading out for the weekend it’s as easy as removing the belt and sporting flat sandals, flip flops or runners!

Check out this one from White House Black Market ($110)

Lightweight Sweater

A lightweight sweater is a must have for summers in the office to keep you warm enough when the air conditioning is blasting.

Work Style: Choose a bright coloured one that can pair well with your dress pants and skirts.

Cottage Style: This sweater is perfect for cool summer nights out too when barbecues  by the water take you late into the evening.

Try the LOFT Shadow Striped Sweater available in regular and petite sizes. ($68.21).

T-Shirt Dress

A T-shirt dress is another wardrobe staple that I believe everyone should have!

Work Style: Be sure to choose one in a length that’s appropriate for work and you can wear it to the office with a cardigan or blazer. Add some elegant jewellery and wear it with either ballet flats or low heels for a very polished work look.

Cottage Style: Remove all the accessories, throw on a pair of tennis shoes and a hat and you’re set for cottage life!

I love this inexpensive option from Old Navy ($14.50).

Linen Shirt

No fabric screams summer more than linen. I’m not even sure what other season is really appropriate to don this fabric but in the summer months it looks very chic and effortless.

Work Style: A linen shirt works perfectly for the office as it can be paired with dress pants and dress skirts easily and makes for the perfect casual Friday outfit.

Cottage Style: When heading to the cottage throw on a pair of jeans or short and wear the linen shirt unbuttoned over a casual tank top. It can also double as a swim suit cover up!

The Gap’s Linen Boyfriend shirt ($64.95) comes in a wide variety of colours and patterns to suit everyone’s tastes. 

 Black Culotte Romper

Looks like rompers and jumpsuits are here to stay! I absolutely love the look of a culotte romper as it can work for both office, evening and weekend! Talk about bang for your buck!

Work Style: For the office pair this smart number with pumps, a blazer and some understated jewellery.

Evening Style: For evening simply remove the blazer and add a statement necklace and some arm bangles.

Cottage Style: For weekend you can easily wear the romper with sandals, ballet flats or even cute white tennis shoes!

Try this Deep V-Neck Culotte Romper from Dynamite ($54.95).

Share with us your favourite weekday to weekend cottage style transition pieces!

Category: Fashion, LivingTag: cottage style, easy pieces for comfortable and stylish summer, update your summer wardrobe

About Elaine Atkins

Elaine Atkins is an everyday girl from Toronto with a love of beauty, style, food, travel, and everything in between. Her interest in beauty and skincare is showcased on her beauty blog Toronto Beauty Reviews while she shares her latest loves and experiences over on the aptly named lifestyle site, Elaine Loves. Passionate about blogging, she lends her expertise to Spark Sessions as the Project Manager, and you can see her work online in publications such as Fashion Magazine and Huffington Post Style.

Previous Post:A (Canadian) World Travel Guide When the Dollar is Falling
Next Post:How to Find Zen In The Laundry Basket

Reader Interactions

Comments

  1. Nicole Boyhouse

    at

    So rompers really ARE here to stay? I just can’t. I can’t! Aieee! Oh well, I can partake in other fashion trends, yes? I had to smile because I’m always freezing in air-conditioned places and so carry a sweater with me all the time, even in Las Vegas when it was 108 because otherwise I’d freeze!

Sidebar

Instagram

Save the Date - Girl Trips

Canadian getaways for women 45+
Click to learn more →

Categories

Here’s where else you can find me:

Girl Trips Logo What She Said Logo

Oh Canada

Travel Here, Not There: 10 Canadian Swaps for Your Favourite U.S. Getaways

Le Boat House Boat at Bevridges Lock

 Heading Out on a Le Boat Trip? Here’s What to Pack (and What to Leave Behind)

Plan a Cabot Trail Road Trip: The World’s Sexiest Drive

Enjoying your time in Pleasantville?

From travel tips to personal stories, Life in Pleasantville is powered by caffeine and curiosity. If this post hit home, made you laugh, or helped plan your next trip, please consider buying me a coffee to keep it going.

Buy Me a Coffee

Connect With Me Online

  • Facebook
  • Instagram
  • Threads
  • TikTok

Inspiration

“Every day is another chance to get stronger, to eat better, to live healthier, and to be the best version of you.”

Recent Posts

Le Boat House Boat at Bevridges Lock
Girls camping in Ontario

Copyright © 2025 · Life In Pleasantville · All Rights Reserved