The Anthony's Guide on How to Dress Over 50
Posted on 21 September 2022

By the age of 50, you’ve made a life for yourself. You’re ready to give yourself a break from the hustle and bustle of life and enjoy the simple pleasures of your existence. Whether this involves sliding into retirement or simply planning more vacations for yourself, there are so many opportunities to take in your surroundings while aging with grace.
Understanding how to dress in your 50s is a simple yet important thing to consider at this time; creating a style for yourself that emphasizes your personality, exudes confidence and prioritizes comfort should always be at the top of mind.
Are you tired of wearing the same basic T-shirt and jean ensemble to every get-together? Are you searching for a cute beach look for an upcoming resort vacation? Just because you’re in your 50s, doesn’t mean you can’t express yourself and look great along the way. It’s all about finding that classic look that matches your body type and personal style!
Here are some tips and tricks on how to dress fashionable at 50, and suggestions on what pieces you can retire for good.
How to Dress Over 50
As you age, it’s important to continue transforming your wardrobe. Understanding how different pieces of clothing can help you flaunt your body, while also remaining stylish and comfortable, can encourage you to feel happier and more confident in your own skin. Here are some of the staple pieces to add to your wardrobe as you learn how to dress at 50 as a woman:
Dark Denim Jeans
Do you remember that perfectly fitting pair of jeans you swore by in your 20s? You can still achieve the same feeling of satisfaction, so long as you invest in the right style. A pair of dark denim jeans, whether bootcut or skinny jeans, can add casual sophistication to your wardrobe.
A Fun Blouse
Everyone needs a fun shirt for the night out on the town. When you don’t feel like dressing up, but you still want to make an impression, a printed blouse can turn heads. Let this piece of clothing encourage you to explore unique designs, fun textures and bold colors.
A Classic Bag
There’s something so powerful about having a memorable bag. Investing in a nice bag, regardless of the size, is a simple way to take your wardrobe to the next level, according to stylist Andrew Gelwicks.
"Accessories are fun! While they are of course functional, they can be transformational for your outfit,” he shared with Town and Country magazine. “A lot of designers are playing around with bag sizes—oversized, super tiny. A woman carrying a 'power' bag demands attention."
A Flattering Bathing Suit
Forget what you’ve heard about bathing suits. You don’t have to stop wearing a two-piece just because you’re over the age of 50.
Bathing suits are all about expressing yourself while providing comfort and protection as you have fun in the sand and sun. There are so many lovely, flattering bathing suit options that can help you achieve this without making you dress outside of your style preferences.
Whether it’s a one-piece swimsuit or a bikini, there are plenty of bathing suit options available for women over 50.

Other Staples and General Style Tips for Dressing Over 50
Beyond the ensemble suggestion above, there are a variety of other pieces of clothing that can help you feel more confident and put together as you age gracefully.
Other pieces to consider adding to your wardrobe when you want to know how to dress after 50:
- A flowy sundress
- A black dress
- Dressy ankle boots
- Sandals and slides
- Statement jewelry
- A blazer
- Bermuda shorts
- Bathing suit coverup
- Cardigan sweaters
- Leather jacket
When it comes to picking out your outfit for the day - or packing for a resort vacation - keep these small but useful tips in mind:
- Get your clothes tailored. When clothing fits the way it’s designed to, it’s more comfortable and appealing. Get in touch with a tailor who can help your clothing fit like a glove.
- When in doubt, keep things simple. Have fun with loud prints and bold colors, but don’t overdo it. There’s nothing wrong with neutrals! Use neutral shades to set the foundation for your wardrobe, and slide in bold colors and textures over time as a way to mix things up in your style.
- Buy underwear that fits comfortably and correctly. When your bra and underwear fit incorrectly, the rest of your wardrobe will follow suit. Make sure you’re wearing a well-fit bra, underwear and shapewear if desired. This can make a major difference in the way you look and feel dressing over 50.
How Not to Dress Over 50
Expressing yourself as you age is an important part of life, but there are still certain style pieces and concepts that should be left in your teens, 20s, 30s and 40s. Here are a few clothing items and accessories you can leave in the past to make way for your new and improved wardrobe:
- Oversized clothing
- Short skirts, shorts and skorts
- Crop tops
- Ill-fitting pants
Learn How to Dress Fashionable at 50 with Anthony’s Florida
Dressing over 50 and expanding your wardrobe can be intimidating, especially if you’ve been dressing the same way for decades. At Anthony’s Ladies Apparel, we want to make it simple and seamless to dress the way you want and feel comfortable and confident along the way.
Our assortment of women’s clothing can help you make a fashionable statement, all while making it easier to be yourself and feel good along the way. From bold colors and sophisticated animal prints, to asymmetrical fashions and standard neutral pieces, you’ll find everything you need to express your style and look amazing while you do it.
Whether you want to completely upgrade your current wardrobe or you’re looking to add a few new staple pieces to your collection, Anthony’s makes dressing over 50 a simple and exciting venture. Browse through our women’s clothing today and you’ll never have to wonder how to dress after 50 again.
Shop our women’s collection now!
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