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Guide: Winter Outfit Ideas – Items to Grab for Cool Casual Style

Guide: Winter Outfit Ideas - Items to Grab for Cool Casual Style - Simply by Simone - Simone Piliero Arena - Winter Roundup with Revolve

While I have learned to enjoy the change in seasons here in New York, by January 1st, mentally I’m over Winter. I don’t care how pretty the snow is, I can’t deal with it being dark at 5:00 pm anymore. And the cold, I really don’t like the cold.

This Winter is of course different – many of us are still staying safe at home and doing way less (if any) things that call for a cute outfit. Yet, I almost find more excuses now than ever to get ready. At a certain point, I’m so over wearing sweatpants and leggings every day.

I try to keep the super casual looks to two days a week. Getting ready every morning sets my day up for success – it’s like making my bed, which also helps me feel a small sense of accomplishment before I even have breakfast.

That said, living in close quarters and seeing all the clothing, trinkets, books, etc. I’ve accumulated over the years has had me reevaluate what I need when it comes to my wardrobe. Having new things to wear makes me feel good – and I want to purchase pieces I can wear for years to come.

Today I teamed up with Revolve to share this roundup that only features items I think you’ll be glad to have in your closet. From working from home at your kitchen table to your future outside the house a bit more, you’ll be thankful to have these versatile items to wear for seasons to come.

Winter Outfit Ideas – Items to Grab for Cool Casual Style

Leather Pants

Leather pants are here to stay. If you purchase a straight or wide-leg or any relaxed cut I promise you’ll like them even more than your matching sweat set.

Winter Outfit Ideas - Items to Grab for Cool Casual Style - Leather Pants - Simply by Simone - #winteroutfit #winteroutfitideas #outfitideas #casualstyle
Winter Outfit Ideas - Items to Grab for Cool Casual Style - Leather Pants - Simply by Simone - #winteroutfit #winteroutfitideas #outfitideas #casualstyle

Wearing: The Nya Pant

Loose Fitting Dress

Comfort or I don’t want it. Place your order, but one size up. Gone are the days of squeezing myself into anything. The added room gives you the opportunity to layer your dress with the turtleneck, long sleeve shirt, or overall be move comfortable throwing a knit over it.

Guide: Winter Outfit Ideas - Items to Grab for Cool Casual Style - Loose Fitting Dresses - Simply by Simone #winteroutfit #winteroutfitideas #winterstyle #casualstyle
Guide: Winter Outfit Ideas - Items to Grab for Cool Casual Style - Loose Fitting Dresses - Simply by Simone #winteroutfit #winteroutfitideas #winterstyle #casualstyle

Wearing: Ira Mini Dress

Leather Shorts

Hear me out – leather shorts are exactly what you need this Winter. They are the epitome of cool casual style vs. their leather skirt counterpart. Leather shorts, tights, a chunky knit, and boots are perfect for any outing this Winter.

Use the TikTok trick and pair skin-toned leggings under your tights for added warmth.

Guide: Winter Outfit Ideas - Items to Grab for Cool Casual Style - Leather Shorts - Simply by Simone #winteroutfit #winteroutfitideas #winterstyle #casualstyle
Guide: Winter Outfit Ideas - Items to Grab for Cool Casual Style - Leather Shorts - Simply by Simone #winteroutfit #winteroutfitideas #winterstyle #casualstyle

Wearing: The Blaise Leather Short

Half-Zip/ Button Up Sweaters

Where preppy meets casual cool. The button-down sweater got its hype back in Winter 2019 but it hasn’t stopped since. The half-zip is having a moment this Winter but I don’t see it going anywhere anytime soon.

Guide: Winter Outfit Ideas - Items to Grab for Cool Casual Style - Button Down Cardigan and Half-Zip Sweaters - Simply by Simone #winteroutfit #winteroutfitideas #outfitideas #casualstyle
Guide: Winter Outfit Ideas - Items to Grab for Cool Casual Style - Button Down Cardigan and Half-Zip Sweaters - Simply by Simone #winteroutfit #winteroutfitideas #outfitideas #casualstyle

Wearing: The Kali Cardigan // The Leslie Half Zip Sweater

Neutrals For the Win

Did you know I’ve been shopping at Revolve since 2005? Recently as I’ve converted to a more neutral wardrobe, I’ve been adding easy-to-wear and significantly more casual items from Revolve. If I’d have to pick one item for you to grab this Winter it would be real or faux leather pants. The cuts this season have been perfect. And they’ll quickly become your new BFF. Move over leggings. 

Use this guide to create the best at-home wardrobe and set a goal to get ready this year – you won’t regret it.

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