Oversized clothes style secrets: when you’re worried trying something new

Styling oversized clothes can be a ton of fun. It’s all about playing with proportions. When it comes to clothes, proportions being the relationship between the clothes + your body, each garment to each other, and your outfit as a whole. 

On one hand it’s a ton of fun. On the other hand experimenting with new styles can feel unfamiliar and sometimes intimidating. Especially when it involves new-to-you proportions. We tend to prefer familiarity over unfamiliarity, so new styles can sometimes get sticky. (Also why it’s sometimes a good idea to keep new clothes visible instead of instantly putting them away in your closet.)

So this post is for you if you want to try styling oversized clothes but are worried. Maybe you’re worried about looking bigger, or messy, or not being able to pull it off. Whatever your concern, here are 3 secrets to help you out.

Learn more about styling garments (oversized and not!) for your body with Holly’s Guide to Dressing for Your Body Shape with Care and Confidence here.

Here are 3 secrets to styling oversized clothes to help you get started.

First things first.

Take what works for you, leave what doesn’t. Experiment, play, adapt these secrets so they work for you and your body. Find what makes you most comfortable. 

Your body is perfect and beautiful. It may seem impossible to believe, but you don’t have to worry. Also, most people aren’t staring. We’re all too busy worrying about our own body insecurities. And we all have days when we’re scared and want to feel more secure. 

Wear what you want to wear, when you want to wear it, and wear what feels good to you. If you try something and it doesn’t work, that’s ok. It just means it’s time to try something else. 

Secret #1: size WAY up

Size way up. When you’re styling oversized clothing, remember that you’re intentionally styling oversized clothing. 

The look you’re aiming for intentionally committing to stylishly oversized clothes.

You want to avoid “I bought the wrong size”. As with so much when it comes to personal style, looking intentional and confident is 90% of pulling off any outfit. (That’s why confidence is the very first thing we cover in 5 Days of Style.)

So sizing way up is the first secret to styling oversized clothes. Exactly how many sizes to size up will depend on: the style of the garment, the fabric of the garment, and the built in ease of the garment. (Ease is basically how close to the body is the garment designed to be. For example, a fitted blouse will generally be designed with less ease than a loose fitting sundress.) 

One to three sizes above the size you’d otherwise wear is a good place to start. 

An aside on clothes sizing.

On the whole, sizing in the fashion industry is a nightmare with no consistency. Each brand has their own standard of sizing. If you’re already towards the top of a brand’s sizing range, you’re going to have fewer options for sizing up your clothes. 

Despite every implied industry and social message – lack of sizing options reflects badly on the brand and the industry. It is not a reflection of you or your body.

Implementing this will be harder for some people than others. Again, having a lack of options is a reflection of the brand and the industry. A lack of options is not a reflection on you as an individual.

Luckily, sizing up is not the only secret to styling oversized clothes.

Secret #2: find your preferred fabrics & clothing structures

Paying attention to the fabrics and structure of your clothes isn’t just for oversized garments. But when you’re worried about styling oversized clothes, fabric and structure are particularly important elements to pay attention to. 

Pretty much any fabric / structure combination can work – but you’ll probably have some types of fabrics and structures that “click” for you and that you feel most comfortable in. Start with those. 

If you generally like wearing structured clothes, start with structured oversized pieces. If you generally like wearing softer & flowy garments, start with soft and flowy oversized items. 

However, if you’re not sure where to start, start with oversized clothes in styles that aren’t intended to be structured or close fitting. Softer, flower garments tend to be a little more forgiving. 

Secret #3: layers

The third secret is layers! 

It may seem counterintuitive to add layers, but it’s not. 

When it comes to layering and oversized clothes there are two generalized extremes. 

Extreme #1: Oversized layers on oversized layers on oversized layers. 

Think stylishly unkempt layering. This style can be a ton of fun if it matches your personal style. But it can be tricky to balance proportions. And you might need to do a little experimentation before you find your comfort zone.

Extreme #2: Second-skin or barely-there under an oversized layer. 

Think bodycon dress + trench coat. Or bikini + beach robe. Or short-shorts + oversized tee. Again, ton of fun if it matches your personal style – but not for everyone. (For more bodycon dress outfit options – including a number of oversized styles, pick up your copy of the “BODYCON! Outfit Recipes for Bodycon Dresses” ebook here.)

If one of these extremes speaks to you – have at it! 

Otherwise, a really simple way to dip your toe into styling oversized garments is to pair an oversized coat / jacket / sweater / etc with a closer fitting dress or top & pant. A classic example of this is a fitted dress with an oversized coat. Or fitted jeans with an oversized sweater.

Final oversized clothing notes

A couple last notes before we wrap up. 

Remember that trying new things with our style can feel exhilarating. It can also touch on some tender parts of ourselves. (And sometimes it can do both at the same time.)

If you’re running into some tender bits, here are some things you can try: 

• Try this new style in one area of your outfit and keep everything else well within your comfort zone. It’s like a variation on 5% fancier – 5% new. 
• Consider starting with clothes & styles that visually lengthen your body (long lines, etc.). If you’re starting to play with oversized styling and already worried, let’s not multiply the worry by also worrying about looking shorter. 
• In that same vein (and this goes for any new style) highlight the parts of yourself that you like. 

And keep a buffer phrase or two in your back pocket.

One last tip for styling oversized clothes

Finally, if you’re struggling to find oversized clothes, it might be time to branch out into new-to-you-brands.

Consider looking at brands that intentionally design for a broader size range, and/or brands designed and marketed towards male bodies. Using a wardrobe inventory to keep track of sizing, and a pocket shopping list to keep track of what you’re on the lookout for, or brands to try, can be extra helpful here.

Remember that wearing and styling oversized clothes is all about playing with proportions and making your choices look intentional. Confidence and looking intentional will go a long way in your personal style journey.

Again, you can learn more about styling garments (oversized and not!) for your body with Holly’s Guide to Dressing for Your Body Shape with Care and Confidence here.