Last weekend, I went for a long weekend in Annapolis, MD and I have to admit-I am totally in love with the city! It is so charming and reminds me of a mix of Newport, RI and Charleston, SC-two places I absolutely love! When packing for the weekend I went for simple outfits and accessories that easily transition from day to night. These outfit combos are my go-to looks for fall so I thought I would share them today along with some of the restaurants we tried while in Annapolis!

All my tops in this post are from Pink Lily, a high-quality, affordable, and trendy online boutique! Most products are made/finished in the USA. I first ordered from Pink Lily this summer and was so impressed by the fit and quality of the items (for very affordable prices)! Pink Lily has a great selection of all things fall-sweaters, sherpas, sweater dresses, and seasonal graphic tees!

Daytime Casual/Coffee Run:

I wore this pullover to get coffee, and someone told me they liked my “fuzz” haha! This pullover is my go-to for staying cozy! I wore it with my favorite moto Spanx ($38 Spanx option linked here), and a pair of $30 Golden Goose dupes.

Brunch/Siteseeing:

Oversized sweater, skinny jeans, and booties look put together and polished but still casual enough for daytime activities. This sweater comes in 5 colors and is under $50! I bought these booties in two colors for fall (wearing tortilla suede here, also purchased in natural embossed leather/snakeskin). The silhouette is so flattering and the heel is low enough to wear all day! Sean and I had brunch at the Iron Rooster-the chicken and waffles was to die! Their special item on the menu are homemade pop tarts-can you say nostalgia?

Dinner/Night Out:

I love the flare jeans/heels combination-it just makes me feel like I can take on the world lol! These flared jeans are so flattering and elongate the leg when worn with heels. The details like the balloon sleeves and slim waist of this sweater are dressy enough to be going-out worthy but still keep you warm on chillier nights. I wore this outfit to Level in downtown Annapolis. Their small plates/tapas style meals were soo delish! My favorite plate we tried was the Duck Confit. Dessert is also a MUST-the cobbler was amazing!

Stay tuned for a life update post this week-I’ll fill you in on why I was in Annapolis and what the future holds for Sean and I! Big changes ahead!