D-I-Y Dee-It-Yourself Shopping Part 1

I would have to think that a common theme amongst M to F crossdressers (like me) is shopping for clothes. As a guy, it’s zero fun. I always say my guy wardrobe is gifts (e.g. Christmas presents), Costco, and race shirts (those you get when you enter a race).

OTOH, shopping for Dee is mega fun. I once said if I can run five hours to finish a marathon I can certainly shop that long.

I know everyone’s circumstances are different, so everyone doesn’t have the same freedoms I do to go shopping. Many in our group limit themselves to online shopping, for a variety of reasons. These days, many women also almost shop online only, like my GG friend Renee, as well as Ms. Dee-ism. While I have bought a handful of items online (most from stores catering to crossdressers), the majority of things I have bought have been in person from bricks and mortar stores (I am also fortunate to be the beneficiary of a number of Hand-Dee-Downs from GG friends, mostly from Michelle).

The main advantage of buying in person is, of course, the opportunity to try things on and see how they look and fit. Depending on how confident and comfortable you are, sometimes you can get a second opinion from a friendly sales angel or a shopping buddy. Or to paraphrase what Kira from Dangerfield once said, “come out and strut your stuff on the catwalk!” It’s simply a chance to try on lots of different things and see what works and doesn’t work. It is incredibly fun to pick up something, tell yourself “no way”–and then try it on and have the mirror tell you “that’s not a bad look”.

Where to go? I’ll list several of my favorite stores. Next week, your second-hand/thrift options (although Kan-Dee should write the chapter on second-hand and thrift options, as she is the undisputed queen of discount shopping). Of course, this is a US centric list–with a bonus pick for down under, as my travels to non-US locations (other than Australia) are extremely limited.

1. Nordstrom. When I emerged from my cocoon in October 2016 my first shopping destination–fresh from a makeover from Sephora–was Nordstrom. I had arranged a room in advance, and sales angel Diamond even called me the day before asking what types of dresses I wanted to try on (my answer can best be summed up as saying “all of them”). The staff at Nordstrom were friendly from Day One (“come back anytime”; “we love you”) and I’ve been to a number of Nordstroms in different cities and I’ve always felt welcome. I usually comb through the discount racks, or will try something on I like, and then wait until it hopefully goes on sale. You can also set up a meeting with a stylist; there is nothing so heart harming as opening a dressing room door to find a roomful of clothes waiting for you to try them on, along with a sales angel to help you decide what works for you.

2. Nordstrom Rack. The Rack sells both items removed from the main Nordstrom outlets plus other brands. Occasionally I will find something that I previously saw (more likely tried on) at Nordstrom’s. I have bought a few things here (there are two in the St. Louis area). If you are looking for shoes, they have racks sorted by size, which generally makes life easier for girls like us. OTOH, the prices, even on discount, tend to be a little higher than I like to pay. But if you don’t know your size, you can always pop into a Rack, and find some different sizes to try on (even if you are in guy mode). They usually have clearance and outlet shoes up to size 12.

3. Dee-Signer Shoe Warehouse. While on shoes, with the passing of the brick and mortar Payless stores (RIP), DSW has become my go to shoe store (because we can never have enough shoes). DSW, like the Rack, has clearance racks, organized by size, usually at the back of the store. It’s another place you can try and find shoes in your size, although they are generally limited to size 11 as the largest. There will also be the occasional shoes in the regular racks that I will try on, although it is generally where I look for my size (11, preferably 11 wide) and then I will see if I like the style. They also have email offers occasionally, so you can apply coupons and the like and buy a nice pair of heels for a reasonable price. You can also buy online and pick up at the store, which can minimize a bit of the embarrassment of buying in person.

4. Macy’s. Macy’s used to have three selling points. Minimal staff, so you got left alone, lots of stuff on discount (some ridiculously so), and lots of changing rooms. Post Covid, a lot of their out-of-the-way changing rooms have been closed, so that is no longer a benefit. Also, the quantity of items on discount–especially in dresses–has gone down quite a bit. During my last buying trip, back in March in Durham with GG friend Renee, we found two extremely cute, fun, and sexy juniors dresses, one for $5 and the other $15, and as Renee says, they were a “hell yes”. Macy’s also often has clearance shoe racks organized by size, and some of the items are reasonably priced, so another opportunity to find shoes in your size.

5. Akira. It’s a store aimed at a younger and more urban demographic, but they do have fun stuff. It tends to be in smaller sizes, but they do have a fair number of sales racks with things for $10, $15, or $20 (I even found a bra top for $1, and bought a second in a smaller size for $1 for GG friend Michelle). If you want to take a stroll on the wild side, find your nearest Akira. The vibe reminds me of Dangerfield.

6. White House, Black Market. I’ve had good experiences in multiple WHBMs. It’s also a favorite of Ms. Dee-Ism, another GG friend. My latest strategy has been to try something on in the store. I like it but it’s full price, so I pass on buying it. However, I will keep an eye on it, and with the ad tracking software these days, WHBM will find me, and tell me something that I have been stalking is now 50% off, and I become more interested. My last two buys have gone on sale, so i have gone into the local store and asked if they have the item in my size. Usually they don’t, but the friendly sales angel will find another store that has it, and that store will ship it to you FOR FREE. For the last two items, once in the store, I find the items are on sale for an additional amount, so I end up buying something I really like for about 25% of the original cost. I will also have a spot in my heart for a fabulous time I had in a WHBM in Chicago.

7. H&M, Windsor. Two stores aimed again at a younger (and smaller) demographic, but I have found things I like in both, and they are spotted across the US.

8. Dangerfield. My favourite Aussie outlet. Multiple fun brands–Princess Highway, Revival, Dangerfield, Black Friday–each with their own feel and style. The sales angels are hip and colourfully dressed (they are required to wear Dangerfield gear) and are very willing to offer their opinions. The main problem is too many choices, and their sizes tend to be smaller than I can fit into (Aussie sizes are also smaller than ours, so a 14 in Aussie is generally about a 12 here). It is my definite go to store when down under.

The above are my regular, go to stores for buying in conventional stores. In Part 2 I will cover the other part of my purchases, thrift stores, so stay tuned.