Before you pack away that summer dress, try it on with tights and boots. Add a knit over the top, and you might have more crossdresser winter outfits you’d happily wear for lunch in November. A summer to winter wardrobe transition can start with the clothes you already love and a few additions you’ll wear repeatedly.
In this article, we’ll cover:
- Adding sleeves to a summer dress
- Turning dresses into crossdresser winter outfits with knits or jeans
- Choosing tights and boots for several looks
- Buying the missing piece instead of a whole outfit
1. Pull out three summer favorites before you shop
Choose three pieces you’d like to keep wearing: perhaps a sleeveless dress, a skirt and a favorite top. Lay them on the bed beside your jeans, knitwear and boots.
Then try the combinations on. That floral skirt might work with a plain sweater you’ve had for years. Your summer camisole could sit under a cardigan, with the lace showing at the neckline.
Take a photo of each outfit you like. If something is missing, write down exactly what it is. “A fitted black long-sleeved top” gives you a useful shopping list. “Some winter clothes” leaves a lot more room for purchases you won’t wear.
2. Put a fitted top beneath a sleeveless dress
If you’re working out how to wear summer dresses in winter, start with a thin, fitted long-sleeved top underneath. Try a plain black top beneath a patterned dress, or a cream one beneath denim.
One of the most useful layering tips for crossdresser winter outfits is to check the shoulder fit again after adding a layer. A dress that fits beautifully on bare skin can become tight once there’s another top underneath. Keep a warm coat for outdoors, and save the lightest summer fabrics for indoor plans on colder days.
3. Wear a sweater over a dress you already own
Pull a sweater over a summer dress and let the lower half work as a skirt. A plain knit over a floral dress gives you a new outfit without buying another skirt.
Long sweaters can hide the waist of your dress. Try a shorter knit, or tuck the hem of a longer sweater up under a belt at your waist to give it a cropped shape. Turn sideways and check the back in the mirror too, paying attention to where the fabric gathers. A lighter sweater is easier to tuck without leaving a thick roll around your middle.
This is also a good way to keep wearing a dress with a neckline you don’t fancy leaving exposed in the cold.
4. Add opaque tights to the skirts you wore all summer
A pair of tights is a small addition that works across several crossdresser winter outfits. For your summer to winter wardrobe transition, try the same skirt with opaque black tights and the boots you already own before deciding it needs replacing.
Black tights with black footwear give you a continuous line beneath a shorter skirt. If you prefer color, pick up a shade from the dress or top. You can still enjoy your summer prints when the temperature drops.
5. Choose boots that work with your dresses and jeans
Get your boots out and have a play with hemlines. That summer midi dress might look lovely falling over the boot tops, especially now you want a bit more coverage. You’re looking for combinations you’ll actually reach for on a cold day, so give your existing boots a proper try before shopping for another pair.
Watch the calf fit when choosing knee-high boots for crossdressers. Jeans take up more room inside a boot than tights, so measure around your calf over the jeans you plan to tuck in. Compare that measurement with the boot’s size guide before buying.
6. Try your summer dress over jeans for more crossdresser winter outfits
Jamie recently showed us this combination, pairing a dress with jeans and boots to dress the look down for autumn. It’s worth trying with something you already own.
Start with straight or slim jeans and a dress that leaves room to move at the hips. A button-front dress gives you another option: wear it open over a simple top and jeans, like a long outer layer. Try it before packing it away. You might discover it gets more use this way than it did in summer.
7. Buy for the outfit you have already tried on
When you’re crossdressing on a budget, it’s easy to buy a bargain dress and then discover you need shoes and a jacket to wear with it. Go back to those outfit photos before placing an order.
If the same cardigan finishes three looks, that’s a useful purchase to increase your crossdresser winter outfits. If a sale item needs several more purchases before you can wear it, leave it for now. Give yourself a spending limit and buy the piece you’ll use first. There’s no need to finish an entire winter wardrobe in one shopping trip.
Your summer to winter wardrobe transition can begin with one outfit laid out on the bed. Try the dress, add the tights, change the shoes, and see what you’ve already got. You’ll have a much clearer idea of what to buy next, and a few favorites can stay out of storage a little longer.
Which summer piece would you love to keep wearing through winter: a favourite dress, a skirt or a top you’re not ready to put away? We’d love to know what you think! Email us at [email protected] or message us on our Facebook page. And be sure to check out more great tips and articles on our blog!