Even if you are a self-proclaimed dress hater, try to keep an open mind and consider, just for a moment, how delightful it is to throw on one piece of clothing, accessorize, and be out the door. Don't lie, you know you like it.
Besides being ridiculously easy, dresses are a great way to break up the monotony of separates.
With these lovely incentives in mind, let's chat dresses. Instead of breaking down dress options by shape, let's start with the seasons.
Summer dresses are arguably the most fun, because there are so many options. The patterns, fabric weights, and shapes are almost endless. Here's what I recommend:
1. If you live in a warm climate (read: Florida, Vegas), I suggest having at least 3 casual summer dresses and 1 more formal one on hand. The casual ones can be any pattern or color your little heart desires, keeping in mind that proper fit is still important when it's hot out and no one wants to see your bum no matter how many sessions you've had with your trainer. The more formal one would be for a wedding, bar mitzvah, etc. and should probably be in a solid color that isn't distracting (I like the ones in the above picture).
2. If you live in cooler weather (hello, San Francisco), you might need 2 casual dresses at most. But if you are a dress lover, I can't fault you for having more.
3. If you like white dresses, do everyone a favor and wear a slip or get one that is already lined. Surely no explaination for this is necessary.
4. Your shoes should be in keeping with the tone of your dress. Black patent leather shoes with a white linen sundress are too heavy and seasonally inappropriate. Try sandals or open-toed pumps in a fun color.
5. Stilettos + grass = muddy heels and increased tripping. Wedges are a perfect alternative if you don't want flats.
Fall dresses tend to be the most versatile both in color and fabric weight. Heavy cotton blends and light wool blends are ideal for the cooler weather, and they transition well from late summer into winter.
I recommend having the following:
1. Wrap dress in a cotton, silk, or wool blend. Perfect with a cami and heels or boots.
2. Shift dress, lined for optimal fit. Great with tights and pumps when it's cool, bare legs and peep toes when its warmer.
3. Evening dress in flattering color. For the theater and cocktail parties.
4. Dress shapes should flatter, not hide, whenever possible. Don't get me wrong, I love the freedom of a trapeze dress, but it's not exactly giving me a waist.
5. Fall is the best time to buy dresses, because the quality of fabric is typically much higher generally than in other seasons. If you want something to last for several years, I suggest looking in the fall offerings.
6. Plaid dresses are pretty juvenile; I prefer my plaid in smaller doses.
I'm not a huge fan of winter dresses because I can't wear any of the snuggly wool options. But just because they make me itchy, doesn't mean you shouldn't try one if you can handle the fabric.
1. Sweater dresses are great, but beware: they are often not flattering, and tend to be highly unforgiving.
2. Please avoid the winter maxi dress at all costs. Just because they are everywhere, doesn't mean you should get one. I will discuss maxi dresses shortly, but suffice it to say that they do not belong in your winter wardrobe. No, not even belted.
3. The maxi dress should not be confused with a long formal gown, which could be useful this season, depending on the kinds of parties you attend.
4. A comfy, long sleeved dress for the weekend is a nice change from the ubiquitous jeans-and-a-sweater and a snuggly yet cool choice with tights and boots.
5. Most, if not all, fall dresses can be winterized with tights, boots, and a jacket or sweater.
If you aren't dress-inclined, you can skip this season all together. Most retailers are trying to sell us resort wear and unless you are going to Tahiti in March, I doubt you need any of it. If you like dresses, though, some spring dresses can liven up what you've been wearing all winter and take you into summer without breaking a sweat.
1. Maxi dress: just do it. They are comfy and cute and you can wear them all spring and summer. Pick one that is fitted on top to balance the volume in the skirt.
2. Color! Now is the time to break up the black and brown with something colorful. Beware the trendy prints. Safari-inspired, ikat, etc. are all cute, but aren't super versatile for most of us.
3. For some reason, denim dresses keep creeping into the landscape. Avoid these at all costs. Run, do not walk, away from anyone who tells you differently.
4. Ruffles. Spring is a fun time to experiment with new shapes and volumes in your dress wardrobe. Ruffles and the one shoulder look are fun; don't go overboard on pattern or color if you choose an already bold shape.
If you own none of these or want pictures for examples of the dresses described above, let me know and I will do a follow up post with pictures and definitions. There are no stupid questions, only stupid purchases.