How To Dress Well on the Way To Reaching Your Goal Weight


Today’s Q&A Thursday topic wasn’t requested by any one listener. But it’s a question that I’ve heard countless times over the past decade plus. I get asked about this issue all the time from friends and family, on podcast interviews, and from women in my community. It’s time to address it fully right here on the podcast. 

The question is: How can I dress well on the way to reaching my goal weight?

Friend, I get it. If you’re in progress on a weight loss journey, you do not want to spend a fortune, or even a penny, on new clothes you hope won’t fit you for long. But we’ve also talked in past episodes about how important it is to look and feel your best TODAY. So what should you do?

Well, I have an answer to this very common conundrum. In fact, I’m going to give you 8 ways to celebrate where you are right now, get dressed with confidence, and look amazing without wasting money on clothes before you’ve achieved those coveted weight loss goals. Whether you want to lose 10 pounds or 10 sizes, this episode is for you.

I don’t want anything holding you back from looking and feeling your best. So let’s make sure you’re well-dressed no matter what size you are today or tomorrow. No more excuses, my love.

1. Mix oversized and fitted pieces

Oversized styles are still trending, so this is a great styling look to try if you’re on a weight loss journey. What I would recommend is pairing oversized pieces with something fitted so you can still show off your figure, celebrate your success, and make sure to avoid looking swallowed up by your clothing. For example, you could wear a fitted top with baggy jeans or a loose oxford shirt unbuttoned with a fitted tank or bodysuit underneath. Don’t hide your shape!

2. Alter your favorite items

If you have clothing items that you love but no longer fit perfectly, consider taking them to a tailor. Tailoring can make a significant difference in how your clothes fit and flatter your body. This way, you can continue to wear your favorite pieces while you work towards your goal weight.

Tailoring costs can range from $10 to $100 or more, so call around for estimates first to help you decide whether it’s worthwhile. 

3. Try a clothing rental service

Here are a handful to explore:

4. Shop size swap programs

Did you know there are stores that will allow you to swap clothing sizes for FREE for one whole year or more? I think this is the most genius and generous solution ever to this extremely common problem. And it makes so much sense if you know you’re not going to fit into the same size clothing within the next few months or even years. I highly suggest checking out these incredible companies:

5. Get trade-in rewards

This isn’t as ideal. But check to see if the brands you love and already shop offer trade-in rewards. Lots of clothing companies, including fast fashion retailers, are making efforts to help eliminate textile waste. I rounded up a handful to give you a jumping off point:

6. Build a micro capsule for your current size

I totally get it if you don’t want to build a full wardrobe you love right now. If you’re actively working to lose weight and this is a healthy and realistic goal for you, it makes sense. That said, I still want you to look and feel your best. One of the things I love to recommend to my clients is curating a really small capsule closet to help you get by in the meantime.

I normally don’t adhere to capsule wardrobe rules like limiting yourself to only 33 pieces. But a super small and well thought out wardrobe could be the perfect solution if you want a few versatile items to sustain you until you hit your goal and feel ready to invest in a full-on closet makeover!

7. Focus on the foundations

The majority of what I call your Style Foundations do not fluctuate with your weight. So it’s never too soon to start dialing-in your signature style, learning how to flatter your figure, or discovering your best colors. You can implement these foundations right now and simply size up or down as needed.

Think about it; Your proportions will not change. Your basic body shape will not change. Your best colors will not change.

There’s a lot you can do right now, exactly where you are, to start dressing yourself at the next level and feel way more confident today. No weight loss required and no need to wait! Start doing your homework now, because these foundations will work for you in every season and at every size moving forward.

8. Think about what lies beneath

If you’re going to buy anything during the process of losing weight, make it bras and underwear. When it comes to styling outfits, one of the most important things is to make sure your undergarments are working to flatter your figure, optimize your silhouette, and give you the smoothest line possible. Because what goes underneath your outfits is what allows your clothes to drape well on your body. So this is an incredibly important step when it comes to putting your outfits together.

Up to 80% of women are wearing the WRONG bra size! Thanks to common weight and hormone fluctuations, experts recommend getting fitted for your bra size every 6 to 12 months —and this is regardless of whether you’re actively working to lose weight.

It’s been said that “good fit brings attention to you; bad fit brings attention to itself.”

So here’s what to look for when it comes to your undergarments. Ideally, you want your bra to lift and separate. Underwear is best left to the imagination, especially under light-colored or skin-tight pants, skirts, and dresses. Take the time to find the right fit and style for your bottoms as well.  

There you go, my friend. We’ve covered 8 ways to dress well on the way to hitting your goal weight.

I hope this empowered you to stop waiting until you reach some destination on the scale and start up-leveling your personal style so you can look and feel your best today. You don’t need to spend much, if anything, to dress yourself well in the beautiful body you have. I’m here to support and cheer you on every step of the way!


leave a comment

Exclusivity Looks Good On You

well, hello there

Get on the VIP list and I'll happily email you weekly style advice and exclusive, personalized content you won't find anywhere else.