As women over 50, we often prioritize comfort in our clothing. Personally, I know I no longer want to feel restricted by tight clothes, and I prefer pieces that provide a little more coverage. After all, clothes are our friends, and with the proper fit (and coverage) they can make us look and feel fabulous! Women over 50 look for comfortable fashion, yet we still want to look chic!
But feeling comfortable doesn’t have to overshadow style. We don’t want to look like we’ve just rolled out of bed in sweatshirts and joggers when we’re out on the town.
5 Comfortable Fashion Wardrobe Must-Haves
Luckily, the fabrics of today allow us to stay comfortable but still look crisp and sharp. Here are 5 fashion pieces I recommend for women over 50 that are almost as cozy as sweatpants—but will leave you looking put-together and chic.
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These wardrobe staples all have one thing in common: you can wear them for hours without feeling uncomfortable!
1. White Shirt With Stretch
A white shirt is a must-have wardrobe staple, and you can get one with a bit of stretch like this one from Lyssé. This shirt is ideal because you can tuck it in or wear it out over a t-shirt, or belt it over a slim pencil skirt or trousers. And it never wrinkles.
2. Long Cardigan Sweater
A cozy, long cardigan is a versatile layering piece that can add polish to any outfit, not to mention warmth. It is a great alternative to a structured blazer, which is not as comfy. The longer length is flattering too. Black is my favorite choice, but this Caslon® long cardigan is also available in grey and olive.
3. Stretch Belt
A belt may not sound like the most comfortable thing to wear, but it is when it is a stretch belt! It cinches your waist and adds shaping to loose or flowy pieces. Even if you feel you don’t have a small or well-defined waist, wearing a belt can be flattering and give you that shape. Give it a try over the white shirt or cardigan sweater on this list. This stretch belt from Target is only $20!
4. Jeans with Elastane
Jeans are a staple in any wardrobe, but when they have elastane (or spandex) they’re a game changer. They stretch and move with you while still holding their shape. The styling of these Mother straight leg jeans are a classic that can be flattering on many body-types and they offer a lot of stretch with 2% polyester and 1% elastane. However, look for a denim style that is flattering on you (skinny, flare, wide-leg, etc.) only make sure it offers at least 2% stretch for all day comfort.
5. Ballet Flats
Ballet flats are chic, comfortable and versatile. But some flat shoes don’t offer enough support for your feet. Vionic makes ballet flats that are podiatrist-recommended because they come with a heel and arch support insole. (It can also be removed so you can replace it with your own orthotic insole.) I like this square-toe style (in black, of course), but why not get the leopard print for added style? You can also choose from wide variety of colors to suit your personal style.
But wait… that’s not all!
A Comfortable Stretch Outfit
These 5 pieces can be worn together as an outfit. Wear the belt over the shirt, over the cardigan, or tuck in the shirt and wear it over the jeans under the cardigan. You get it— there are plenty of options and everything has stretch!
This look is perfect for the office, going out to a restaurant, happy hour with the girls, or any time you want to feel comfortable and stylish. These pieces are your new sweats!
What do you wear to feel comfortable and look chic? What is your must-have wardrobe piece?
You may also like to read Trendspotting Fashion and Beauty in Japan: How To Get The Look and Pantone’s Top 10 NYFW Fashion Color Trends For Spring 2025.
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