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The How and Why of Upgrading Your Style Game

Winter is here, and that means it’s time for more clothes including layered sweaters and jackets, cute tops, and warmer dresses, to name just a few. But more clothes mean more clothing decisions, and that’s not welcome news to everyone. For those of us without a knack for fashion, the season to start “really dressing” can be a fraught one. 

You can get by this winter by bundling yourself into a big coat and skipping the layers and fashion-forward details — but you shouldn’t. You don’t have to be a naturally style-conscious person to appreciate the ways in which dressing well can improve your mood and your life. And you should know that upgrading your style game doesn’t have to involve hours of research and massive amounts of money. 

Why dressing well matters 

If you’re not into fashion, you might have a negative idea about what fashion is. You might consider it shallow or vain. When you hear that how people perceive our attractiveness and confidence can affect our career prospects and our love lives, you might find that news frustrating. 

It’s okay to be frustrated, but don’t assume that fashion is just about impressing others or glorifying ourselves. To many, fashion is a hobby or a passion. To others, it’s simply a way to respect themselves. Dressing well makes you look your best, which is something we should all enjoy. Like taking the time to shower or work out, it’s a sign of healthy self-care and is part of a broader lifestyle that will make us look and feel good. 

Fashion and mental health are connected, believe it or not. Simple rituals like dressing well can boost our self-esteem. Looking our best can improve our confidence, and confidence is key to everything from career success to personal relationships. Take the time for fashion! 

How to make a style change this winter 

If you’re ready to make a change to your style, that’s great — but how can you do it? Some of us may assume that investing in personal fashion means lots of research and fashion magazines, not to mention lots of expensive purchases at fancy boutiques. 

That stuff is perfectly valid if you’re into it, but you don’t need to obsess over fashion or spend big in order to look your best. In reality, a few simple rules and some smart spending will serve you just fine. 

For starters, you need to consider fit and body type. Fashion details come and go, but flattering fits are much more permanent. You should shop around at different stores and check out different styles. Look for the ones that accentuate the best parts of your body and avoid highlighting things you don’t like. 

Start with fashion essentials which include dresses, tops, and pants that you’ll be able to wear in a wide variety of settings. Get things you can wear to work and then feel good in when you stop at the bar for drinks after hours with coworkers. Get fancier garb that will suit a dinner party or religious services. And think about classic colors and designs that are easy to mix and match. Playing with color can be a lot of fun, but building a basic wardrobe means starting with versatility and moving to specialty items from there.


Buying a bunch of new clothes is pricey, of course, which is another reason to start with the basics and build out only when you’re comfortable. But there are other ways to save money, too. One big one is to shop online. This doesn’t necessarily have to mean giant ecommerce companies, but rather curated online boutiques — hip online shops that have the same kind of stylish threads as their brick-and-mortar cousins do. Online boutiques offer the sweet spot between high-quality fashion and low prices.


By focusing on fits and basics and buying quality long-lasting clothes from online boutiques, you’ll build a foundation for your style that will last. And when you experience the joys of dressing well, you’ll want to keep shopping for more and more variety.