4 life-changing tips to stay stylish during weight loss (Ya know, when your clothes don’t fit right)

As a professional Personal Shopper I’ve worked with nearly every type of body and firmly believe people of all sizes can up their style game. Whether you’re currently trying to lose weight, recently had a baby, or just having trouble dressing your current size and shape, I am here to help.

And guess what? I’ve been there!

I’ve been a size 2 (post-break-up stress) and a size 12 (ate my feelings for years) so if weight fluctuations have you in-between sizes or confused about how to navigate an ever-changing wardrobe, below are my go-to, proven tips to being stylist during weight loss.


“I won’t feel good until I lose weight.” 

Regardless of size or shape, the right outfit makes us shine with confidence. How do you create those outfits every day? Especially when you feel you have “nothing to wear” and things aren’t fitting well?

If clothes have you feeling less then an attractive powerhouse, try this:

Follow good feelings to great outfits.


Pay attention to how much an outfit/item makes you feel good as soon as you see yourself in it. Ruthlessly eliminate what doesn’t give good feelings. Keep modifying the outfit by adding, subtracting or swapping out items (shoes, accessories, clothes) before the look feels “right and good”.


“My body isn’t there yet. It’ll be easier/smarter/better to dress stylish once I hit my weight loss goal.”


Reward yourself for where you are and the success you’ve had (creating life, losing weight, loving your body in this decade). It’s motivating to see ourselves in a positive light NOW and wearing sizes that aren’t flattering doesn’t encourage healthy consistency or self-love.

Instead of wearing what you have and making do with what is “good enough” do this:

  1. Audit your closet ASAP.

  2. Separate what fits well now and what doesn’t. Donate or resell anything you’re over.

  3. Put too-small, keepable items in one section of your wardrobe for wearing later on.

  4. Out of items that are too big, determine what you would like to wear right now.

  5. Bring the too-big clothing to a tailor and have them corrected to fit you well. If it can’t be tailored, donate them.

  6. Keep tailoring items and shifting the closet according to your weight loss/lifestyle. If you buy something new, you can tailor it down too, when or if weight loss makes it necessary. 

  7. Anything that eventually becomes too big can be brought to the tailor as needed.

  8. Edit, edit, edit. Use this process during your journey until the only thing that remains is what makes you feel and look good. (see #1)


“Buying new clothes feels like a waste of money and time.”

After #2, you may find yourself longing for a few new things.

Focus on items that adapt!

A note on menswear - men have it a little easier if strictly buying nice shoes and accessories. They can also tailor almost everything or buy low-cost replaceable pieces (i.e. t-shirts) and keep their style simple. This option is available in womenswear as well, but female body shapes and diverse clothing options can make it more limiting or difficult to discern your .

Now is the time to shop smarter:

  1. Buy flowy dresses, blazers, jumpsuits, grandpa sweaters, shoes, bags, sneakers and accessories into your wardrobe.

  2. Play with styles that you would love to wear now in items that don’t bring fit challenges (like jeans).

  3. Buy beautifully crafted accessories and classic low-cost pieces (t-shirts, tailored shirts, fine knits) for simple yet sharp style.

  4. Give your attention to fashion (trends, colors, fabrics, appliques) that excites you in pieces that will adapt.

This approach won’t waste money and you’ll be more satisfied with your wardrobe edit in the long run. (See #1+2)


“I’ll focus on my appearance when I lose the weight”!

NO! You are not defined your body weight/size/shape. 

You can look and feel better now. Do this:

Dress your natural-I-born-with-it features and use them as an accessory to your outfits.

Focusing on these features helps because that uniqueness isn’t changing (at least for a loooong time). Dress to impress by accentuating what you love in your appearance and giving less attention to what you don’t.

So, if you love your long legs, broad shoulders, beard or sexy raven-like hair, then flaunt. If that means more trips to the barbershop and bangin’ beard oil, then invest accordingly. Take these features to the next level by advancing grooming or wearing outfits that draw attention to it.

Developing “forever” style tricks will enhance your image while bringing in confidence - and compliments - not related to size. It’s a fantastic way to practice seeing the good in yourself too!