Glamour Boutique

Breastforms, Bodyshaping and Affordable Crossdressing

Shopping Bag

Ask Katie: Is There a Proper Order When Dressing En Femme

Discover the smoothest, most stress-free way to transform, as Katie breaks down the perfect step-by-step order for your transformation.

Table of contents:

  • Body Prep
  • Shapewear
  • Clothes
  • Makeup
  • Wig
  • Finishing Touches

Dear Caroline,

Trust me — you’re far from alone. We’ve all been there- smudging makeup onto a cute top, sweating off half our makeup while squeezing into a corset, or having to restyle our wig completely after it snagged on a dress. A polished transformation often comes down to one thing: the order you get ready in. Once you follow a clean step-by-step routine, everything suddenly becomes easier, faster, and a lot more fun. Here’s the sequence that tends to work best for me, especially when you’re using shapewear, forms, makeup, and a wig to create your final look.

1. Start With Body Prep

Kick things off with anything that helps you feel clean and confident: a shower, shaving (if you choose), moisturizing, deodorant — the basics. Prepped skin makes your clothes glide on more comfortably, helps makeup sit better, and reduces that “last-minute scramble” energy.

2. Shapewear

This is your foundation- literally. Put on:

Breast enhancement (breast forms, breastplate These items usually require pulling, adjusting, smoothing, and wiggling. Installing them early means you won’t risk smearing makeup or disrupting your wig. If you’re using a breastplate or any piece that needs to go over your head or shoulders, now is the perfect time to put it on!

  • , bra)

3. Clothes

Slip into any tight, pull-over, or fitted clothing. Think: body-hugging dresses, tops that sit close to the skin, bodysuits, slips, camisoles — anything that takes a bit of effort to pull on. Putting these pieces on before your makeup and wig ensures you won’t accidentally smudge your face or knock your hair out of place while struggling with tight fabric. You can leave zippers or buttons undone for now. The goal is simply to get the clothing on so you can secure everything neatly once your hair and makeup is finished!

4. Makeup

Once the tugging and adjusting are behind you, you can dive into the beauty side of your transformation. If you use a wig cap and/or face tape, do it during this stage—before any makeup. Wig capping and taping early allows you to position everything smoothly and then blend makeup on top for a seamless finish. Doing makeup at this stage protects it from clothes rubbing against your face and ensures your wig will frame a flawless canvas.

5. Wig Time

Once your makeup is complete and set, it’s time for the wig. This step ties the whole look together! Secure your wig, apply adhesive now if you use it, and position your wig exactly where you want it. Brush it, shape it, fluff it — whatever makes you feel the most feminine. Doing hair after your makeup ensures everything blends seamlessly and nothing gets smeared or shifted.

6. Finishing Touches

This is where your look comes alive. Save these items for the end:

  • Earrings, necklaces, rings
  • Belts & Jackets
  • Perfume
  • Heels or boots
  • Handbags
  • Any last smoothing, buttoning & zipping

These final touches don’t interfere with makeup or hair, and they complete the fantasy in the most satisfying way.

When everything is done in a thoughtful order, your transformation becomes smoother, quicker, and far more enjoyable. With practice, the entire process becomes its own relaxing ritual — one that lets you step confidently into your most feminine self without the frustration of backtracking or redoing steps.

With love,

Katie

Remember if you have any questions on the subject of crossdressing, Katie can help. From relationship advice to tucking to sizing. Ask away and Katie will gladly answer all emails sent in to [email protected] Make sure to add ‘For Katie’ into the Subject Line.